6 Books and 8 Steps to Endurance Running Success

Endurance Running - WhyWhatHow.xyz
Endurance Running - WhyWhatHow.xyz
The Marathon des Sables, 2016
Day one of seven – Only 256km to go!

Perfect for you if:

  • You’re fit, motivated and starting to become serious about endurance running.
  • You’re preparing for your first (ultra)marathon, especially the Marathon des Sables (MDS).
  • You’re rehabilitating from a running injury.

“Full of very succinct and good advice… as a general guide to help people prepare for long distance challenges like the MDS, I think your blog is excellent.”
Julian Goater, National Cross Country record breaker, twice world age-group duathlon champion and author of The Art of Running Faster

“A clear, concise and true account of what to expect in an endurance race. Some really level headed and rational advice.”
Marina Ranger, 18 Time Ultra-marathon and Ironman Competitor

A couple of years ago I was asked by a friend if I wanted to run the Marathon des Sables (MDS). We had 10 months to prepare. Neither of us were anything close to what you might call “endurance runners”. Personally I’d never run much more than 5km in one stretch in my life.

In the end four of us went along with his crazy scheme, raising ~£30,000 for charity in the process. Two of us finished in the top 250 (of 1,200). My friend and I placed in the mid pack (~600). That was despite him breaking both his little toes, losing eight toe nails and having half the skin on his feet sanded off by the Sahara (the photos are gruesome!). Looking back, the training and race were one of the most challenging and rewarding experiences I’ve ever had.

One of the first things I did was to buy as many books on endurance running as I could. I then synthesised the best of these into a set of notes (below) which informed my training plan. Looking back on the experience I’m incredibly glad I did this. Our timeline from fairly fit to MDS worthy was short and the notes helped avoid most major “new runner” pitfalls. At one point I did pick up a knee injury. Thanks to my research I was able to get back up and running as quickly as possible without major complications.

To keep the notes below concise I’ve stripped out the extra detail on preparing specifically for the MDS. I might break these down in a future post. For now, here’s my raw MDS training plan, kit list and nutrition plan. What’s left below is hopefully a useful starting point for general endurance running / ultra marathon training!

Where a section lacks detail I’d recommend referring to the books below or a Google search. This is probably because that section gets very detailed (e.g., fixing your feet), academic (e.g., training periodicity) or controversial (e..g., nutrition). In those cases I’ve tried to link to a good resource that wraps up the main points well.

I was never a runner before training for the MDS but it’s now an important part of my life. Running keeps me fit whilst I’m on the road and is an amazing way to explore new places and meet new people. As a keystone habit it’s also been incredibly powerful for bringing about far reaching positive change to my life.

Good luck with your training and if you have any hints/tips/opinions then please do leave a comment!

Six Books every Endurance Runner Should Read

  • “Born to Run” – Chris McDougall – From the African Savannah, to the Mexican Copper Canyons and Nike’s factories – Chris takes running back to basics in his critically acclaimed book on evolution, injury and recovery. Compelling insights, great story telling and practical insights abound. A must read.
  • “Eat and Run” – Scott Jurek – If you’re going to take advice from anyone you could do worse than the most well-known and successful ultra marathon athlete of our time. Scott’s proof that veganism is compatible with world class athleticism alone would make this book a must. Definitely one to read and refer to.
  • “Field Guide to Ultra Running” – Hal Koerner – Hal dispenses with story telling in favour of a wealth of practical, down-to-earth tips on endurance running. This essential endurance running guide is full of trail running techniques, race strategies and even detailed training plans for 50km or 50 and 100 mile ultras. One of the most helpful books I read.
  • “The Art of Running Faster” – Julian Goater – A fantastic running primer, especially on the bigger picture elements of running (e.g., mindset and training cycles). Julian’s book is a superb supplement to Hal’s guide with a slightly more track focussed and academic flavour.
  • “Survival of the Fittest” – Mike Stroud – I didn’t read this book before the MDS but wish I had. Full of anecdotes from the author’s own experiences and some great insights into Nutrition, Evolution and Physiology. If you’re still hungry after McDougall and Jurek then this book is definitely worth picking up.
  • “Fixing your Feet” – John Vonhof – If endurance running is your trade then your feet are your tools. Nowhere will you find a book that covers the topic so comprehensively. Perfect for you if you’ve ever had a hot-spot, blister or toe-nail trouble. If you haven’t, you will. This bible on foot care will save you a world of pain!

Extra Credit

Anyone training specifically for the MDS might also enjoy “Running from Shadows” by Mark Roe. A humorous and well written account of one office warrior’s experience training for and completing the race.

This Discovery Channel documentary featuring Olympic rowing gold medallist James Cracknell also made for part inspiring, part terrifying pre-race viewing.

The Runner’s World website is a treasure trove of high quality writing on all things running. No matter what I type into Google on the subject it usually comes up top of the results. Well worth checking out.

Eight Steps to Endurance Running Success

  1. Bring the Right Mindset.
  2. Don’t Get Injured.
  3. Work on your Technique.
  4. Practise Purposefully.
  5. Sculpt your practice into a long-term plan.
    • Set a goal >>
    • Build in milestones >>
    • Periodise your training >>
  6. Fuel yourself for success.
  7. Race smart.
  8. Use the right tools.

1. Bring the Right Mindset.

50% of endurance running is in your head. That’s why, when it comes to running, mental toughness is as important as physical fitness.

Remember these tips whenever you feel demotivated or find yourself dreading training sessions:

Decide to love it not to fight it.

  • Keep training fun (don’t over fixate on performance).
  • Periodically run without gadgets and goals.

Adopt a growth mindset.

  • No plan survives first contact with the enemy.
  • Expect the unexpected both in training and on the race.
  • Relish each setback as an opportunity for learning and growth.

Expect nothing in return.

  • It’s not the goal, it’s how you get there.
  • Do it for yourself, not for others.

Share it.

  • Join a running club and/or run with others (if possible)
  • Share your running highs and lows with friends and supporters.
  • Give back; run for charity, help other runners.

2. Don’t Get Injured.

It is amazing what the body can withstand and achieve with small, steady, compounding improvements. That is why the Golden Rule of becoming a better runner is not getting injured.

  • Consistent gains come from consistent training, but
  • The biggest enemy of consistent training is injury, and
  • The majority of injuries are avoidable.

What’s more, the advice to runners who do pick up an injury is clear:

  • Don’t train on an injury; and
  • Don’t overcompensate coming back into your plan.

The pressure of catching up on missed training is powerful. Do not succumb to it. Injury cycles can last for months or even years. Once you slip in, it can be very hard to escape.

Here are some steps you can take to stay ahead of the pack:

Know your enemy (see APPENDIX: Running Injuries).

  • Learn the causes, early symptoms, preventative measures and treatments of common complaints.
  • This will help you catch them early and prevent setbacks.

Be patient with your training.

  • Overtraining leads to mental and physical fatigue.
  • Fatigue will wear you down and compromise your form.
  • Never train so hard that you lose form (this exacerbates overtraining and causes most injuries).

Work on your technique.

  • Poor technique is at the heart of many chronic injuries.
  • Over striding and heal striking are the worst offenders.

Remember that the first and most important goal of every training session is completing the next session.

3. Work on your Technique.

For a great primer on technique, check out this timeless 4 minute classic from ultra marathon legend Scott Jurek.

Speed (distance per minute) = cadence (steps per minute) x stride length (distance per step).

First, focus on high cadence and light feet. This will help you avoid injury and increase efficiency.

Then, adjust stride length (without compromising cadence) to control speed.

Here are some of characteristics of a good running technique:

Feet (run with quick, light feet):

  • Use a fast cadence (180 strikes per minute).
    I use a free metronome app on my phone set to 180 bpm to help with this.
    It may feel uncomfortably quick at first but will quickly became natural.
  • Land on mid/front of the foot.
    The key here is to avoid heal striking – a major cause of knee and back injury.
  • Land lightly (listen to your feet).
  • Strike below or behind your hips.
    Otherwise you’re heal striking and wasting energy coming over your foot.

Posture (imagine a rod from head to foot strike):

  • Lift your head up.
  • Look at the ground ~5 yards out.
  • Stand tall.
  • Straighten your back.
  • Open your chest.
  • Relax your shoulders.
  • Bend your arms 45-90 degrees.
  • Do not cross your body with your arms.
  • Bend your knees slightly.

Form (think of running as controlled falling):

  • Lean forward (but without bending forward)
  • Think of an efficient cycling movement.
    • Lift your knees to pull you forward.
    • Flick your heels back to push you forward.
  • Use your arms.
    • Arms are integral to shifting bodyweight quickly.
    • Cadence is often limited by arms rather than legs.
    • Feel shoulders (not elbows) pulling back and down one at a time (but keep them relaxed).

Breathing (breathe deeply through your nose):

  • Breathe through your nose.
    • Breathe easily, no need for gasping.
    • Reduces heart-rate and perceived stress.
    • If you can’t breathe through your nose you may be running too hard.
  • Set a consistent rhythm (breathe in for 3 + steps, out for 3 + steps).
  • Practice using your whole lungs (be mindful to avoid shallow breathing).

4. Practise Purposefully.

REMEMBER: The golden rule of training is to be able to complete the next training session.

Give each training session a clear focal point.

Good running requires training in ALL of these skills (even/especially for endurance).

  • Focus on honing one skill per training session (six Ss).
    How and when to focus on each S will make more sense after section 5.

    • Skill
    • Stamina
    • Strength
    • Suppleness
    • Speed
    • (P)sychology
  • Train twice a day on non-long run days.
    • Breaks up the distance.
    • Provides twice the training focal points.

Vary the conditions you train in.

  • Surface (road, trails, sand, mud):
    • Variable surfaces will build ankle strength and reduce the risk of injury.
    • Be careful of road cambers, they can skew technique and cause injury.
  • Weather:
    • Get used to running in the wind, rain, snow, heat, cold, humidity.
    • Learn to relax into and embrace adverse conditions, not fight them.
  • Times of day:
    • Run at dawn, mid-day, dusk and night time.
    • The unique challenges of each will help generalise your conditioning.

Using a variety of training techniques each week.

  • Easy runs:
    • These should form the bulk of running sessions.
    • Run at 60 – 70% (enough to carry a conversation) without checking a watch or worrying about pace.
    • Treat these as a good opportunity to experiment (with terrain, mileage, running partners).
    • You may feel easy runs are “junk miles” but they add to the foundation and build strength and muscle memory.
      Weekly mileage is the best predictor of race performance.
    • Finish with Strides (100m bursts of 95% speed with 2 min cool down, sets of 4 – 12).
  • Long runs:
    • 30 (- 50% if racing back to back marathons) of your weekly mileage.
    • For ultras, longest run should be about 60 – 70% of the distance you will race
    • Back to backs are great for building time on the feet and logging miles
    • Use these to experiment with race nutrition and gear.
    • Careful not to increase by more than 10% per week.
  • Special training sessions (see APPENDIX: Special Training Sessions):
    • e.g., fartleks, tempos, intervals, hills, barefoot, spectrum and resistance training.
    • Include a few each week to stress a particular focal point.

* I found aiming for a heart rate of ~ 160 BPM worked well for me when running without a partner.

Supplementary training

  • Strength training:
    • Core strength (esp. stomach and back) is key to running.
    • Go to the gym and train regularly on top of your running.
    • Aim for 200 crunches every morning in addition to your gym sessions.
  • Stretching:
    • Suppleness increases range of motion and efficiency as well as reducing risk of chronic injuries.
    • Best performed consistently; before and/or after and separately (e.g., Yoga) to training.

5. Sculpt Your Practice Into a Long-term Plan.

Sign up for a Race.

Sign up for a race, whether competitive or fun.

  • Races are a great way to structure your training.
  • Have fun with it, pick a race that will take you to new places and people.
  • Always remember that the race is a training aid and not an end in itself.

Set multiple goals for the race.

  • Choose a target pace / time based on previous results.
  • Set A, B and C goals (e.g., top 100, personal best, finish race).
  • This will help you adapt your plan to reality leading up to / on race.

Train specifically for your race.

  • Know the course and its demands.
    • Type of running (back-to-backs vs. long runs).
    • Conditions (temperature, time of day, surface, hills).
    • Recommended/required gear.
    • Nutrition requirements/options/limitations.
    • Hydration approach (and limitations e.g., rationing).
  • Replicate these demands as much as possible in training.

Sign up for Practice / Milestone Races.

Sign up for milestone races e.g., one third and two thirds of the way to your main race.

  • Creates a forcing mechanism.
  • Gives you an indicator of progress.
  • Creates realistic conditions to test your gear, nutrition and hydration.

Periodise your training

Macro Periodisation (Training Cycles):

  • Periodisation is about structuring your long-term training plan to maximise fitness.
  • There are many different opinions on “best” practice and it can get pretty academic pretty quickly.
  • Experiment with what works best for you, do some research, ask other runners or join a running club.
  • For now, here is a basic overview of major periods for a 16 – 20 week training plan:
    • Base (~8 weeks) – Take it easy, focus on easy and long runs.
    • Specificity (~6 weeks) – Start brining in some Special Training Sessions to focus on eg., endurance, speed and recovery.
    • Peak (~2 weeks) – Ramp up and push the boundaries of over-training. This shouldn’t feel sustainable but don’t get injured!
    • Taper (~2 weeks) – Cut training down to almost nothing. Stretch, do some acclimatisation.
    • Race – The big day(s). Don’t forget to stick to your plan!
    • Recover (~4 weeks+) – Very light training. Why not try e.g., swimming.

Micro Periodisation:

  • You can take things even further by periodising within your macro periods.
  • E.g., run harder than the period average for 3 weeks then take it easier for 1 week.
  • This can help keep your sessions varied, speed up gains and avoid fatigue.

6. Fuel yourself for success.

Caveat: Do not overthink general nutrition. It is the quickest way to make your life and running habit miserable.
A little education goes a long way and you will find yourself naturally changing your diet as your running progresses.
Be wary of general rules: nutrition is highly individual. Experiment. Have fun. And trust your body.

Think of food as fuel:

On the run:

  • Inputs:
    • Carbohydrates
    • Salts
  • Vectors:
    This is a highly personal choice – experiment on your training runs and mix up flavors to avoid monotony.

    • Energy Gels
    • Energy Chews
    • Electrolyte mixes
    • Energy drinks
    • Natural foods (e.g., Chia seeds, nuts, chocolate milk for recovery)
    • Salt tablets
  • Process:
    • For carbs, aim for 300 – 400 calories an hour.
    • For salts, aim for 200mg (easy conditions) to 400mg (tough conditions) per hour.
    • Use a watch to monitor your caloric intake closely and don’t get behind.

Hydrate before it’s too late:

  • Get used to drinking on the run while training
  • Do not get behind on water intake (this is a main cause of ultra race dropouts)
    • Once dehydrated it is very hard to catch up.
    • Severe dehydration can lead to Hypertonia as the kidneys shut down.
    • Aim for 600ml per hour (20 – 40 sips @ 15 – 30ml per sip) in easy conditions and much more in harsh conditions.
    • Use a watch to keep to a strict drinking regimen.

7. Race Smart

Have a plan for the race:

  • Set multiple goals (pace/time)
  • Train for those goals (don’t expect to suddenly run faster on race day)

Stick to the plan on race day:

  • Start slow, finish fast (it takes at least an hour for the adrenaline to wear off)
  • A big part of endurance running is discipline: start steady and stick to a plan

8. Use the right tools.

Very personal. I’m a Brooks Cascadia (designed by Scott Jurek) fan but each to their own!
Use the Taco test to check if your current shoes are compromised: if you can bend the forefoot past 90 degrees it’s time for a new pair!

  • Don’t skimp, go to a specialist running shop.
  • Avoid too much support (this can weaken your foot).
  • Think about trail shoes vs. trainers (some trail shoes have self cleaning soles).
  • Wear shoes that allow you to run down hill without jamming your toe.
  • Anticipate foot swelling of at least half a size.

Socks (very important):
I always run with an inner layer of Injinji toe socks and have (so far) never had a blister.

  • Blister management = moisture management.
  • You get what you pay for, avoid cottons (terrible wicking).
  • After contact with water, change socks or use a hairdryer at next aid station.
  • Try different combinations of socks during training (don’t leave it to race day!)

Watch (with GPS)
Very personal choice. I’m a huge fan of Suunto’s Ambit Peak range.

  • Critical for timing nutrition, hydration.
  • Also important for sticking to planned pace.


  • Cover up in light clothing / colours.
  • N.B., Wearing less is not always the best option for staying cool.

Compression gear may / may not help with recovery and may provide some benefits whilst running:

  • Compression shorts
  • Calf sleeves


  • Wear this around your waist.
  • Keeps it stable allowing head movement.
  • Also lowers angle increasing depth perception.
  • Bring spare batteries.


  • Is good but make sure you can still hear what (and who) is going on around you.
  • In early stages of training it can be helpful to hear your feet to make sure they stay light.

Water bottles:

  • Many different styles and varieties available.
  • Practice with your bottles before a race to check for leaks / customisations.

APPENDIX: Common Running Injuries

Fixing your Feet

If endurance running is your trade then your feet are your tools. Look after them and they will look after you. Failing to do so will result in catastrophic blisters, toe nail loss and injury causing alterations in technique.

Nowhere will you find a book that covers the topic so comprehensively as John Vonhof’s “Fixing your Feet”. In the meantime here are some basic pointers:


  • Equipment:
    • Invest in high quality footwear.
    • Check the lining often for snags and bumps.
    • Replace it as often as required.
    • Learn some basic alternative lacing techniques.
    • Experiment with types and layers of socks.
  • Training:
    • The best way to get your feet used to endurance running….
    • …is to spend lots of time on your feet.
  • Treatment:


  • Taping
  • Lubricants – consider shoe lubricants and powders to reduce friction


  • Intervention
    • Never try to run through a hot-spot – it will become a blister.
    • Much better to lose 5 minutes than drop out of a race entirely.
    • Replace wet socks with dry ones as soon as possible.
  • Bandaging – learn the basics of treating blisters.

Chronic ailments


  • Runners knee – irritation at / around where the kneecap (patella) rests on the thighbone.
  • Achilles tendinitis – dull or sharp pain along the back of the tendon, usually close to the heel.
  • Hamstring issues – pain in the back of your thighs or butt (also sometimes lower back pain)
  • Plantar Fasciitis – a sharp stab or deep ache in the middle of the heel or along the arch of the foot.
  • Shin Splints – diffuse pain in the lower part of your shins.
  • Iliotibial Band Syndrome (ITBS) – swelling and pain on the outside of the knee.
  • Stress Fractures – a specific point of acute pain on a bone (usually lower leg or foot).


  • Mental
    Demotivation / depression are common symptoms of mental fatigue.
    Sleep / rest. Have fun and check your mindset hasn’t become overly performance focussed.
    If all else fails, take a break from formal training and / or running entirely!
  • Physical
    An abnormally elevated resting heart rate is a dead give away for physical fatigue or illness.
    Be mindful of overtraining and make sure you’re getting enough sleep, rest and food.
    Pushing yourself too hard when you’re physically fatigued is a sure route to injury.

Acute ailments


Musculoskeletal (muscle, ligament, bone)


APPENDIX: Special Training Sessions

Fartleks (“Speed play“):
Stress-free workout that improves mind-body awareness, mental strength, and stamina.

  • Unstructured speed experimentation
  • Decide as you feel like it to sprint, run fast, jog…
  • … for 30 seconds, to the next lamppost, past a cyclist

Hill training: General
Challenging but absolutely critical workout that builds strength and speed

  • Long Hills: Build up to 2 – 3 miles up a consitent gradient
  • Hill Repeats: 2 – 3 minutes uphill running at an all out effort. Repeat 3 – 12 times depending on the workout.
  • Practice both up and down hill running but only one at a time.
  • If no hills, use a treadmill (better than nothing!).

Hill training: Uphill

  • Uphills make you run properly (front strike, arms moving) so note the feeling on them.
  • Practice running strongly off the top of a hill to leave other racers behind.
  • Don’t eat during a climb (while heart rate elevated), eat at the top, you will need the energy for the descent.

Hill training: Downhill

  • A good downhill is harder to master than a good uphill.
  • Find a line and look where you want to go (5 meters ahead).
  • Keep gravity over the centre and let gravity do the work.
  • Keep cadence fast and land on your mid-foot.
  • Use a duck stance if the descent is technical to avoid lateral ankle roles and increase stability.
  • Maintain breathing and stay relaxed.
  • Use sunglasses/a visor to help stop air get into your eyes.
  • Spread arms wide like an airplane for balance.

Tempo training:
Increases lactate threshold to run faster at easier effort levels. Improves focus, race simulation, and mental strength.

  • Warm up and cool down with a consistent fast effort in the middle
  • If you can talk easily, you’re not in the tempo zone, and if you can’t talk at all, you’re above the zone.
  • Pace is not an effective means for running a tempo workout, as there are many variables that can affect pace including heat, wind, fatigue, and terrain

Interval training:
Improved running form and economy, endurance, mind-body coordination, motivation, and fat-burning.
See e.g., structured speed training, progression runs and negative splits.

  • Short, intense work outs followed by an equal or slightly longer recovery e.g., two minutes hard, two – three minutes recovery.
  • Unlike tempo workouts, you’re running above your red line and at an effort where you are reaching hard for air and counting the seconds until you can stop.
  • The secret is in the recovery. Patience and discipline while you’re running easy allows you to run the next interval strong and finish the entire workout fatigued but not completely spent.

Barefoot training:

  • Modern trainers can weaken the foot by providing too much support (leading to injury).
  • Progressive and occasional barefoot running is good to strengthen feet.
  • Start with 5 – 10 mins then work slowly up to 30 – 45 mins.
  • Choose a soft surface e.g., grass.

Spectrum training (deliberate extremes)

  • Helps to push you out of your comfort zone and discover new things (esp. in absence of a coach).
  • Examples:
    • Strike as far forward on your foot as you can for 2 mins.
    • Run as fast as you can for 2 mins.
    • Increase cadence to max possible for 2 mins.

Book Crunch: “The Power of Habit”, Charles Duhigg

The Power of Habit, Charles Duhigg

The Power of Habit, Charles Duhigg

“The Power of Habit”, Charles Duhigg
Print length: 402 pages. Buy on Amazon.

Perfect for you if:

  • You’re under the illusion that you’re in conscious control of most of your life.
  • You want to start a new habit but just can’t seem to make it stick.
  • You want to kick a bad habit but keep falling off the wagon.

Charle’s Duhigg’s “The Power of Habit” is a primer and guide for anyone that is fascinated by or has struggled with habits, cravings and willpower.

The idea that habits are a powerful driver of behaviour is not a new one. William James was one of many to observe that:

All our life so far as it has definite form, is but a mass of habits – practical, emotional, and intellectual – systematically organised for our weal or woe, and bearing us irresistibly toward our destiny, whatever the latter may be.

However it is the author’s astonishing breadth of sources and pulitzer worthy story telling that makes this book a classic on the subject. From classical and sports psychology to rehabilitation programs, big business, government and cultural movements; Charles sets about demonstrating that habits dictate most of what goes on around us, whether we see them or not.

Most powerful of all are the practical implications of Charle’s writing. Anyone who knows first hand the unstoppable destruction of craving and addiction can benefit from this book. But so can people looking to make small, positive changes in their lives. Even CEOs and leaders of communities and societal change can benefit from its insights.

The book’s closing sections touch lightly on the thorny nature of free-will and the ethics of habit. Charles concludes that habits can and do exert a power that may go beyond our conscious control to moderate. Changing those habits when we know about them, however, is within our control and a failure to try and change something you know about amounts to negligence.

This book teaches us not just what habits are but also how to change them. What follows is the essence of its main arguments.

The Anatomy of Habit

At some point, we notice that: Cue + Response => Reward.

  • Cues are combinations of stimuli (sight, smell, taste, touch, sound, thought).
  • Responses are chains of thoughts and/or actions.
  • Rewards are increases/decreases in pleasant/unpleasant sensations, emotions or thoughts.

As a result, we practice the response until it becomes a reliable and automatic habit.

  • Repetition triggers long-term changes to the brain’s structure (learning).
  • Coordination becomes independent of conscious decision making.

With time, the brain begins to expect and crave the reward as soon as the cue arises.

  • Cravings emerge even before the habitual response takes place.
  • Even similar cues (near misses) can begin to trigger these cravings.

These cravings then begin to drive responses that deliver the reward.

  • Cravings are powerful enough to override even basic survival instincts.
  • Physical cravings are mostly short lived (e.g., nicotine in blood stream < 100 hours).
  • The mental component tends to be much more powerful and enduring.

The Roles of Habit

As individuals we rely on habits to free up our limited conscious resources.

  • Our conscious attention and working memory are limited.
  • Yet we must respond to thousands of stimuli throughout the day.
  • We manage this by delegating most of our responses to the subconscious.

As companies we rely on creating or changing the habits of our customers to sell our products.

  • Companies have become masters of understanding and manipulating habit cycles.
  • They understand cravings, create new ones and identify and exploit periods of change.
  • Understanding our own habit loops as individuals can help us spot and limit this manipulation.

As groups we rely on habits (laws, processes, routines) to encourage sustainable cooperation.

  • Organisational habits reduce the time and cost of making decisions.
  • Good habits set clear common goals and rules for reward and punishment.
  • Poor habits leave accountability ambiguous and undermine cooperation.

As societies we rely on habits to make major changes / movements sustainable.

  • Societal change moves initially through strong (friendships) and then weak (community) ties.
  • But sustaining this change is effortful so long as its behaviours are a disruption to “normal life”.
  • To make the movement self-sustaining, leaders must set new habits and sustain the movement until these habits become the status quo.

The Properties of Habit.

Habits Are Prone to Relapse.

Habits can’t be erased.

  • Habits result from structural changes in our brains.
  • Once formed, these structural changes decay very slowly.

They can only be overridden by conscious willpower or a new, deeper habit.

  • The subconscious always follows the path of least resistance.
  • But we can use willpower to override a habit with a new behaviour.
  • Or to bridge the gap between a new habit and a deeper one.

But willpower is limited in capacity and endurance (like a physical muscle).

  • We can’t lift e.g., 3x our maximum weight at once nor 60% of it for three hours.
  • It can be strengthened through patient practice (but only within limits).
  • And willpower strength correlates highly with success over time.

This is why deep, old habits are prone to relapse.

  • Cravings drive habits that reinforce themselves.
  • And cues can be persistent and out of our control.
  • Eventually, willpower can become overwhelmed, leading to relapse.

Habits Cascade Like Dominos

The outcomes of habits are often cues for other habits.

This is why changing just one “keystone” habit can have far reaching effects.

  • It can eliminate cues for habits further down the chain.
  • It can establish cues that create new or trigger other, existing habits.
  • It creates a period of wider change and a sense of belief in change.

But not all habits are effective keystone habits.

  • Some habits are better positioned to trigger cascades than others.
  • Keystone habits are often those that benefit from changes across many different areas. e.g.,
    • Quitting smoking might not lead to starting running or improving your diet,
    • But starting running might encourage you to do both and more.

How to: Create a Habit

1. Identify the desired response.

  • Work on one new thing at a time.
    New habits need willpower and willpower is limited. Don’t bite off more than you can chew.
Remember, keystone effects may naturally trigger more change than you think.
  • Make it easy to follow through.
    Plan/prepare/do what you can in advance to make the new response easy to complete.
    e.g., put gym clothes on first thing for running, lay things out the night before for early rising. 

2. Select a cue.

  • Choose one or more of the following to establish as a cue for your response:
    • Location
      Somewhere unique that supports this habit (e.g., a library for studying)
    • Timing
      A regular time each day / week works best
    • Emotional state
      Is the trigger for this new habit excitement? anger? anxiety?
    • Other people
      Who will trigger the new habit? a spouse? a colleague? a friend?
    • Directly preceding sensation, thought or action
      What series of steps will trigger this response? Is it another habit?
  • Visualise the cue and plan out / rehearse your exact response to it in your head.

3. Design some carrots.

  • Treat yourself.
    Use something that makes you feel good like a small piece of chocolate, or chatting with friends.
    Be thoughtful about what new habits this reward itself might create.
  • Establish support networks.

    Find one or more people to tackle the habit and/or check in with to keep you motivated.
  • Visualise your desired outcome and remind yourself of it often.
    Write a clear visualisation of your end goal, print a photo, save a video etc…
  • Track progress and celebrate small wins.

    Small wins reinforce the behaviour and create a positive cycle of belief in change.

4. Set up some sticks.

  • Commit yourself to your new resolution on paper.

    Those who write down resolutions are ~10x more likely to complete them.
  • Track streaks of completed responses.

    The threat of breaking a long streak is a simple yet powerful motivator.
  • Make a public commitment, especially to your weak-ties (acquaintances and communities).

    People whose opinion you care about but who are not so close they won’t judge you if you fail.

5. Practice your new habit cycle every day for 30 days.

The structural changes that underlie habits are triggered only by extended, consistent practice.

How to: Change a habit

Caveat: There is no single formula to change a specific habit.

  • Every person has different cravings and drivers for the same routines / behaviours.
  • Some habits are simple to break down, others are complex and require prolonged study.
  • Some habits can be changed quickly, others are more obstinate.

1. Choose the existing response that you want to change.
e.g., snacking, web browsing, smoking, waking up late, nail biting, stuttering

2. Experiment with rewards.
Rewards are often obvious in retrospect but hard to uncover.
e.g., snacking mid-afternoon may be more about taking a break than the need for sugar.

  1. Give yourself a few days, a week or even longer.
Don’t put yourself under pressure to change in this period, you’re just collecting data.
  2. Adjust your responses to test different rewards and determine the craving driving your routine.

    e.g., eat an apple instead of a cookie, take a break and socialise instead of snacking.
  3. After the response, jot down the first three sensations, emotions or thoughts on your mind.

    This creates momentary awareness. and helps with recall later.
  4. Set a timer for 15 minutes.

    Give the response and reward time to take effect.
  5. Review your notes and ask yourself if you still feel the same urge.
    If no: you have found the reward that satisfies your craving.
    If yes: the reward is something else, try again.

3. Isolate the cue.

Like rewards, cues are often obvious in retrospect but hard to uncover.

  1. Each time you feel the craving arise make a quick note of:
    • Where you are
    • What time it is
    • How you feel
    • Who else is around
    • What you’ve just been doing or thinking about
  2. Review your notes for patterns to identify the cues for your craving.
    e.g., craving to take a break takes place between 15:00 and 16:00

4a. Either: Eliminate the cue.

  • Many cues are directly within our control.
  • The quickest way to stop a response is to simply eliminate the cue.
    e.g., block websites, delete apps, disable notifications, end relationships.
  • Eliminating cues is powerful because it requires no willpower.

4b. Or: Design an alternative response that delivers the same reward (see Create a Habit).
Some cues are not possible or practical to eliminate e.g., times of day, location of work, colleagues

N.b., Periods of major external change and crisis can uproot even old and entrenched habits
These periods give us and others a licence to shake up old habits and act in new ways.

  • Major external changes include e.g., starting a new school, getting married, moving home, changing job, having a child.
  • Crises include e.g., health scares, bankruptcy, accidents or near misses, global financial crises.
Fabricating or artificially prolonging a sense of crisis can be useful when promoting change in yourself and others.

Further Reading

“Thinking Fast and Slow”, Daniel Kahneman – A deeply insightful and Nobel Prize winning piece of work on the psychology of human misjudgment. A little hard work to get through but well worth it. I’ll be crunching this book at some point soon.

“Eat that Frog!”, Brian Tracey – I first picked up one of Brian Tracey’s books when I was 19 and it is no exaggeration to say that it changed my life. One of the best writers on habit forming, goal-setting and general life-acing out there.

“A Mind for Numbers”, Barbara Oakley Book crunch here. A superb book and practical guide on the psychology of learning. Barbara touches on habit forming in her excellent primer.

“Deep Work”, Cal Newport Book crunch here. Cal’s book focuses specifically on building the habit of deep work. Its insights are both fascinating and practical.

“The Marshmallow Test” – three and a half adorable minutes of scientists torturing small children with marshmallows. A modern revival of the classic Stanford experiment.

TANQ entries for 'The Power of Habit'

TANQ is WhyWhatHow’s growing central library of thoughts, anecdotes, notes and quotes.

“The brains dependence on automatic routines can be dangerous. Habits are often as much a curse as a benefit.”

Charles Duhigg The Power of Habit

“Cravings are what drive habits.”

Charles Duhigg The Power of Habit

“It seems ridiculously simple, but once you’re aware of how your habit works, once you recognize the cues and rewards, you’re halfway to changing it.”

Nathan Arzin The Power of Habit

“When people join groups where change seems possible, the potential for that change to occur becomes more real.”

Charles Duhigg The Power of Habit

“A habit cannot be eradicated – it must, instead, be replaced.”

Charles Duhigg The Power of Habit

“Habits are most malleable when the Golden Rule of habit change is applied: If we keep the same cue and the same reward, a new routine can be inserted.”

Charles Duhigg The Power of Habit

“The habits that matter the most are the ones that, when they start to shift, dislodge and remake other patterns.”

Charles Duhigg The Power of Habit

“Routines are the organisational analogue of habits.”

Geoffrey Hodgson The Power of Habit

“When people start habitually exercising, even as infrequently as once a week, they start changing other, unrelated patterns in their lives, often unknowingly. Typically, people who exercise start eating better and becoming more productive at work. They smoke less and show more patience with colleagues and family. They use their credit cards less frequently and say they feel less stressed. It’s not completely clear why But for many people, exercise is a keystone habit that triggers widespread change.”

Charles Duhigg The Power of Habit

“Families who habitually eat dinner together seem to raise children with better homework skills, higher grades, greater emotional control, and more confidence.”

Charles Duhigg The Power of Habit

“Making your bed every morning is correlated with better productivity, a greater sense of well-being, and stronger skills at sticking with a budget.”

Charles Duhigg The Power of Habit

“Keystone habits offer what is known within academic literature as ‘small wins.’ They help other habits to flourish by creating new structures, and they establish cultures where change becomes contagious.”

Charles Duhigg The Power of Habit

“Willpower is the single most important keystone habit for individual success.”

Charles Duhigg The Power of Habit

“Among the most important benefits of routines [(organisational habits)] is that they create truces between potentially warring groups or individuals within an organisation” [Is the same true for potentially warring parts within us?]

Charles Duhigg The Power of Habit

“Good leaders seize crises to remake organisational habits [and] crises are such valuable opportunities that a wise leader often prolongs a sense of emergency on purpose.”

Charles Duhigg The Power of Habit

“People’s buying habits are more likely to change when they go through a major life event [and] there’s almost no greater upheaval for customers than the arrival of a new child.”

Charles Duhigg The Power of Habit

“People, it turns out, often go to the gym looking for a human connection, not a treadmill.”

Charles Duhigg The Power of Habit

“To sell a new habit… wrap it in something that people already know and like.”

Charles Duhigg The Power of Habit

“A movement starts because of the social habits of friendship and the strong ties between close acquaintances.
It grows because of the habits of a community, and the weak ties that hold neighbourhoods and clans together.
And it endures because a movement’s leaders give participants new habits that create a fresh sense of identity and a feeling of ownership.”

Charles Duhigg The Power of Habit

“All our life, so far as it has definite form, is but a mass of habits – practical, emotional, and intellectual – systematically organized for our weal or woe, and bearing us irresistibly toward our destiny, whatever the latter may be.”

William James The Power of Habit

“There are these two young fish swimming along and they happen to meet an older fish swimming the other way, who nods at them and says ‘Morning, boys. How’s the water?’ And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes ‘What the hell is water?'”

David Foster Wallace The Power of Habit

“Water hollows out for itself a channel, which grows broader and deeper; and, after having ceased to flow, it resumes, when it flows again, the path traced by itself before.”

William James The Power of Habit

“Some habits yield easily to analysis and influence. Others are more complex and obstinate, and require prolonged study. And for others, change is a process that never fully concludes.”

Charles Duhigg The Power of Habit

Book Crunch: “The 4-Hour Work Week”, Tim Ferriss

Four Hour Work Week - Tim Ferris

“The 4-Hour Work Week”, Tim Ferriss
277 pages – Paperback | eBook | Audiobook

Perfect for you if:

  • You’re sure there must be more to life than just living to work.
  • You’re thinking about starting your own business but aren’t sure how.
  • You work from an office (when you could be working from anywhere).

“The 4-Hour Work Week” is a powerful book on lifestyle design for anyone that wants to put living before working. I was 19 years old when it first changed my life. Fast forward 10 years and I am amazed at how many of my habits it still influences.

Tim’s goal is to show the reader not only how to design their ideal lifestyle but also exactly how to get there. He combines eye-opening insights and compelling stories with detailed guides and resource lists. The result is a book so full of practical life changing advice that it is very hard to take in on one reading.

There is one catch: Tim offers a reality so alien to most of us that it can be easy to dismiss as unrealistic or unattainable. As an ex McKinsey consultant I can sympathise. The truth though is that Tim’s reality is very attainable. In the last 4 years of travelling the world I have myself met many people living some version of their own 4-Hour Work Week. This includes my Australian girlfriend, Erin, who I met at a Salsa class in Medellin, Colombia.

That said, if there is a major flaw in Tim’s book it is his tendency to favour the catchy ideal over the realistic. Most paths to Tim’s promised land are neither simple nor straight. For many, such a radical shift in world view will mean changing many comfortable habits and beliefs. That process alone is a long one of gradual experimentation. Even then, few will hit on a BrainQUICKEN (Tim’s own success story) on their first or even fifth attempts. Nor will every idea last forever, or be an overnight success. It took Erin 7 years to build her company (along side regular jobs) to the point of becoming a full time “digital nomad”.

But the rewards of experimentation and persistence are worth the effort. As I type this post from St. Petersburg, Russia, Erin is sat across the room, quietly expanding her business into two new continents. She already earns more than most McKinsey partners. What’s more, she does this working less than 5 hours a day (an intense period) from wherever she wants to in the world. Right now we’re half way through a 3 month trip through the Baltics and Scandinavia. Later we’ll plan our next ‘mini-retirement’: two months living in Tel Aviv with adventures in Oman, Jordan, Egypt and Morocco. Even if you don’t know many people like her – I can promise you that her story is far from unique.

In the following crunch I’ve tried to draw the main story line out of the book. I’ve also included as much detail on the step-by-step guides as possible. For brevity, I’ve omitted the pages of helpful resources included throughout the book.

Read this book. Take action on Tim’s suggestions. They may not make you an overnight millionaire that works four hours per week.

But they will change your life.


Book Crunch

Life is short and we play it by outdated rules.

Life is short.

  • We get ~ 30,000 days / 720,000 hours.
  • We spend much of this time asleep.
  • We are rarely fully in the present moment.

And we mostly conform to a status quo.

  • We work at specific times.
  • We work in specific places.
  • We work for ~45 years then retire.

But the status quo is antiquated.

We are influenced by protestant morals of suffering and self-sacrifice.

  • Less is seen as laziness (e.g., face time valued over productivity).
  • Living to work is championed over working to live.

And our work patterns were designed for the industrial revolution.

  • Factory shifts (working at specific times)
  • Limited communication (working in specific places)
  • Demanding, physical work with no safety nets (work hard and young, retire late)

And the status quo is unscientific.

It is unproductive (bad for business):

Unhealthy (bad for us):

  • Stressful: Undefined (de)stress rather than good purposeful (eu)stress.
  • Sedentary: Long hours indoors, at desks, looking at screens.
  • Meaningless: Unimportant activities feel/are meaningless.

And ineffective:

Batching retirement doesn’t make sense.

  • Financially – retirement ages and savings plans do not reflect life expectancies.
  • Physiologically – energy and interest are cyclical.

Neither does batching self-improvement.

  • You cannot relive your youth no matter how youthful you are in later life.
  • The opportunity cost of missing compounding self-improvement is high.

Major upgrades and alternatives do exist.

It’s being done – many case studies are easily and freely available.

  • Pick any number of books or stories from the 4HWW.
  • Since quitting my own job I have met many, many people who have made this kind of life a reality. I would never have met them in the course of my old life.

What’s more, improvements are universally accessible:

  • Whether entrepreneur or employee
  • With or without children
  • Young or old

And the benefits are significant:

  • Greater productivity
  • Better health
  • More fulfilment

Despite this, we often fail to take action.

Because we don’t know how.

  • We don’t know what we want.
  • We don’t believe it’s possible.
  • We don’t know how to do it.

And/or because we are afraid:

  • Of what could go wrong.
  • To let go of what we have.
  • Of what others will think.
  • To admit we might be wrong.

There is a different path, but only you can choose to walk it.

First, you must reconfigure your assumptions and beliefs.

Changing habits takes time and reinforcement, be patient with yourself.

Always ask “Why? Why? Why?”: just because it is, doesn’t mean it should be.

  • Kill the sacred cows: test your basic assumptions about life and the status quo.
  • Question their source: Why do I believe this? Is this a received truth? Have I questioned it?
  • Be honest and don’t fool yourself to spare your ego (consistency bias).

But remember balance: Things in excess become their opposite.

  • Pacifists become militants, freedom fighters become tyrants.
  • Blessings become curses, help becomes hindrance.
  • Different is better only when it is more effective or more fun.

Do what you fear most, it is usually what you most need to do.

  • We often fear what we least understand or threatens to undermine our world view.
  • This is why fear is often our best teacher – move towards not away from it.
  • Here are some simple tricks to help:
    • Understand and accept that the timing is never right.
    • See life as a big experiment: don’t get too attached to the results.
    • Live by the mantra “There is no such thing as failure, only feedback”.
    • Define the worst case: Is it really so bad? How could you mitigate it?
    • Write down every excuse you can think of: How how could you solve each one?
    • Consider the financial, emotional costs of inaction – can you afford not to act?

Get comfortable with psychological discomfort.

  • Being different will make others feel uncomfortable, and that’s ok.
  • Get used to letting small bad things happen so you can focus on the big things.
  • Have the courage to be the one to propose solutions others can build on.
  • Make lots of mistakes, admit them openly to yourself and others.
  • Seek forgiveness rather than asking permission.

Get used to letting small bad things happen.

  • You cannot please all of the people all of the time.
  • To do the big things, you must sometimes let small bad things happen.

Set unrealistic goals, they are often easier to attain than realistic ones.

  • We overestimate what we can achieve in a day, we underestimate what we can achieve in a year.
  • Aiming for a higher goal incentivises better performance and more creative solutions.
  • The fishing is best where the fewest go (there’s just less competition for big goals).
  • Our failed scenario is often better than the outcome of the realistic goal.

Remember that “money” and “things” are only as valuable as the freedom they create.

  • Time and freedom are your most valuable and irreplaceable assets.
  • This is why relative income is more valuable than absolute income ($1k in 2 h > $2k in 6h).
  • Freedom of What, When, Where and with Whom also multiply the value of money (allow you to do more with less).
  • Understand that everything you own has a call on your time; this is the reason the things you own end up owning you.

Then, “Define” what you want – motivation requires motive.

Whenever you feel lost or purposeless, return to this stage.

Initially: ‘Dreamline’ excitement into your life

  • Imagine you have $100m in the bank and are the smartest person you know.
  • What would you: “Have”, “Do” and “Be” in the next 6 and 3 months.
  • Convert any “Be”s to “Do”s to make them actionable.
  • Pick any 4 things on your list to set as goals.
  • Calculate the financial cost (ongoing, monthly).
  • Calculate the monthly / daily income needed to make them a reality:
Target Monthly Income = [ Monthly Goals + (One Time Goals / Total Months) ] * 1.3 Monthly Expenses
  • Define the next actions to move you closer to those goals (Today, Tomorrow and the Day After).
  • Complete those actions by 11 A.M. each day.

Later: Fill the void

  • Financial freedom is just the beginning of the journey.
  • Eventually many things which excited you will lose their thrill.
  • Existing outside of conventional society may also feel socially isolating.
  • This loss of external structure and meaning often leads to an existentialist vacuum and depression.
  • Stick with it, you are not alone! Defining your “Who” and choosing your “Why” are daunting but liberating.
  • It doesn’t much matter what purpose you choose – many tend towards continuous learning and serving others.
  • Once you’ve decided, act. Your new source of meaning will reconnect you with the world around you.
  • You could also seek out and connect with others who share these values and circumstances. *
  • Most important of all: fill your life with different projects and enjoy the social rewards of life.

* Locations with high lifestyle to cost ratios (e.g., Medellin and Berlin) are good places to start.

Next, “Eliminate” all but the non-critical to create time and space.

N.B., employees should see the next section, “Liberate”, before they “Eliminate”.

Be efficient (do things right) AND effective (do the right things).

  • Doing something unimportant well does not make it important.
  • Requiring a lot of time does not make a task important.
  • “What” you do is more important than “How” you do it.

Do only what matters: Apply the Pareto principle (80/20) to your happiness.

  • In your personal life: friends, social groups, commitments.
    • We are the average of the 5 people we spend the most time with.
    • Life is too short to fill it with poisonous or even neutral relationships.
  • In your business: customers, advertising, affiliates, partners, committees.
    • Which 20% of the customers deliver 80% of the profit / problems?
    • Which 20% channels of channels drive 80% of the traffic?
  • Begin distancing yourself from anything on the wrong side of the curve.
  • Experiment initially. Make permanent anything that shows results.
  • Repeat the process every two weeks for your business and personal life.

Do it faster: Apply Parkinson’s law to your work time:

  • Ask yourself: How would you get your work done tomorrow if:
    • You only had 2 hours per day?
    • You only had 2 h per week?
  • Write down max 2 mission critical items and test by asking:
    • Would I be satisfied with my day if only they happened?
    • What are the consequences if they don’t?
  • Complete these tasks by 11 AM the next day
  • Don’t multitask.

Stop doing unimportant things: Lack of time is actually a lack of priorities.

  • Identify the activities you use to avoid doing difficult/important things.
  • Write a not-to do list (e.g., email shuffling, web browsing, status meetings).
  • Ask yourself frequently: am I inventing things to do to avoid the important?
  • Don’t waste time and energy on things you can’t define or influence.

Practice selective ignorance.

  • “News” is often time consuming, negative, irrelevant and outside of your influence.
  • Processing information also costs time and energy and is often not immediate or important.
  • Experiment with cutting down on both by:
    • Trying a one week media fast:
      • No news whatsoever
      • No non-pleasure television
      • No non-task related web browsing
      • No non-fiction books
    • Letting others synthesise for you:
      • Talk to people who know what you want to know.
      • Trust their synthesis of the subject.
  • Ask yourself “Will I definitely use this for something immediate and important?”
  • Practice the art of non-finishing: let go of sunk-costs.

Decimate emails.

  • Set up rules (automatic or via assistant) to eliminate or defer unimportant emails.
  • Streamline responses to prevent back and forth (be specific, provide alternatives).
  • Wean yourself and others off instant email gratification.
    • Use “Limited access to email” autoresponders to train response time expectations.
    • Divert urgent enquiries to an urgent only phone number.
    • Divert non-urgent enquiries to a voicemail (that can be emailed to you).
  • Batch emails to as few concentrated sessions per day as possible (aim for 2 or less).

Eliminate interruptions.

  • Free up time by saying no to low consequence work and commitments (keep excuses vague).
  • Reduce switching costs by batching time consuming and repetitive work (e.g., emails).
  • Prevent bottlenecks by trusting and empowering others to act for you.
    • Trust beyond your comfortable zone (but set up protections).
    • Empower: “Fix anything that costs less than 100 USD”.
    • Review and adjust periodically.

Avoid meetings where possible.

  • Refuse meetings without clear objectives.
  • Force clarity by requesting an email with specific objectives / outcomes.
  • Solve any objectives you can by email, then by phone and only then if you must in person.
  • Force others to the point and avoid chit-chat.
    • Set a defined end time (use a real/imaginary next commitment).
    • Keep things short (< 30 minutes).

N.B., Don’t sight of your dreams: remember, work and money are means not ends.

  • Don’t micromanage and email to fill time.
  • Don’t handle problems your outsourcers or co-workers can.
  • Don’t reply to emails that won’t result in a sale or that can be answered by an FAQ or autoresponder.
  • Don’t strive for perfection when good or simply good enough will do.
  • Don’t blow minutiae and small problems out of proportion as an excuse to work.
  • Don’t make non-time-sensitive issues urgent to justify work.
  • Don’t handle the same problem twice: set up rules and processes instead.

Now, “Automate” what ever is left.

Entrepreneurs struggle here because they fear giving up control.
Employees should first “Liberate” and then return to “Automate”

Outsource what is left and cannot be eliminated.

Outsource whatever you can to focus on more important tasks.

  • Never outsource what can be eliminated.
  • Never delegate something that can be streamlined and automated.
  • Tasks must be time consuming and well defined.
  • Have fun with it: professional and personal tasks.

Hire a Virtual Assistant (VA).

How to: hire a VA.

  • Avoid single point failure (consider an agency/team vs an individual).
  • Measure cost per completed task (consider impact of e.g., cultural / language barriers).
    • India / Philippines (4 – 15 USD per hour) vs.
    • Europe / America / Canada (25 – 100 USD per hour).
  • Request exactly what you need (e.g. types of task, excellent english, phone calls required).
  • Interview and trial several VAs with a difficult task on a short (48h) deadline.

How to: outsource tasks.

  • Define the task precisely:
    • No ambiguity
    • 2nd grade English
  • Assign only one task at a time.
  • Break the task up into 24/48h chunks.
  • Set a 3h check in for any task.
  • Set clear priorities within the task.
  • Create rules and define processes to handle frequent questions / scenarios.
  • Empower and trust others (e.g., fix if under X), review weekly > monthly.

How to: mitigate risk

  • Never use the new hire and prohibit VA firm subcontracting.
  • Avoid debit cards for online transactions (hard to reverse if fraud).
  • Create new unique log-ins and passwords for each VA.

Create an automated income stream.

Start with the end in mind.

  • Aim to “own” a business rather than “run” or “work for” it.
  • Keep it simple: Don’t try to create the next Amazon.
  • The goal is cashflow for low time investment.

Launch a product based business.

  • Scalable and not a function of time (unlike service businesses).
  • Start small – test a minimum viable product early and cheaply.
  • Think big – design and develop the business to scale.

Step 1: Aim at a specific and affordable niche.

  • Creating demand is hard. Filling demand is much easier.
  • What niches do you belong to / understand? Which of these have their own interest/hobby magazines?
  • Look for repeat, direct advertisers in these – the more frequent their ads, the more profitable the niche.

Step 2: Brainstorm (do not invest in) products.

  • Encapsulate the main benefit in one sentence – What is it? For who? How is it different?
  • Price high then justify: aim for a 50 – 200 USD retail price point.
    • Less competition than the mid-range.
    • Fewer, better customers.
    • Higher profit margins.
  • Create a margin of safety: aim for 8 – 10 x markup.
    • i.e., 5 – 25 USD unit cost
    • Get pricing for 100, 500, 1,000 and 5,000 units
  • Additionally aim for a product that:
    • takes max 3 – 4 weeks to manufacture (ideally 1 – 2 weeks)
    • is explainable in a good online FAQ (not ingestible)
    • is testable for < 500 USD
    • is automateable within 4 weeks
    • will require < 1 day per week of management

Create, License or Resell a product (in that order of preference).

  • Creation: New product or private labelling.
  • Licensing: profitable, can be complex (fees ~ 3 – 10% of wholesale).
  • Reselling: lowest profitability, shortest life span (wholesale cost ~ 40% of retail).

Information products are a great choice (high margin / difficult to duplicate).

  • Create them yourself (see generating credibility).
  • Repurpose public domain content (check local copyright laws).
  • Licence or compensate an expert (~3 – 10% royalties on sales).

There is a simple formula to generate credibility when creating information products.
Member of AAA organisation, trusted by BBB University and CCC companies, featured in DDD publications

  • Join trade related organisations.
  • Read the three top-selling books.
  • Give one free, two hour seminar.
    • At a nearby major university.
    • At the local branches of a big company.
  • Write for trade magazines.
    • Either: Use credibility generated above.
    • Or: Offer to interview an expert.
  • Join e.g., ProfNet to become a source of quotes for journalists.

Step 3: Micro-test.

Micro testing uses inexpensive adverts to test consumer response prior to manufacturing.

  • Intuition and experience are poor predictors of profitability.
  • Don’t ask people if they would buy, ask them to buy.

A good micro testing strategy has three stages: (i) Best, (ii) Test, (iii) Divest or invest.

  • Best: Create a 1 – 3 page website with a more compelling offer than the competition (1 – 3h set up).
  • Test: Test the offer using a 5 day Google Adwords campaign (3h set up).
  • Divest / invest: Cut losers and roll out winners.

(i) Best the Competition.

  • Look out for and collect adverts that catch your attention in print or online.
  • Visit the three sites that consistently top the search and PPC positions for your product’s keywords.
  • Write a more compelling proposition (use the collected adverts as models).
    • More credibility indicators (media, academia, associations).
    • Better guarantees, selection, shipping, testimonials.

(ii) Test viability.

  • Buy a domain and set up a simple 1 – 3 page website to captur conversions.
    • Capture contact details via an online form or calls to your phone.
    • Redirect to an “out of stock” or apologise re the same.
    • Don’t capture billing data (illegal before manufacture).
  • Set up Google Adwords campaigns with 50 – 100 search terms at < 50 USD per day.
    • Keep terms as specific as possible.
    • Aim for second through fourth positioning.
    • Pay no more than ~0.20 USD per click.
    • Focus ad copy on the differentiators.
    • Test variations (headlines, guarantees, product and domain names etc…).
    • Disable serving of only best performing Ad.
    • Aim for qualified traffic only (don’t try and trick people).
  • Alternative options include setting up an eBay auction and then cancelling last minute.

(iii) Invest or divest.

  • Review data from testing phase.
    • What was the click through rate? Which adverts performed best?
    • How many conversions on site? Where/when did abandoners leave?
  • Estimate potential demand and profitability from conversion data.
  • Consider improving the offering (e.g., a better guarantee) and trying again.
  • Decide to invest in the product or move on to another idea.

Step 4: Rollout and automate.

This is where most entrepreneurs get stuck.

  • They fail to move on from bootstrapping and replace themselves.
  • The reward is a scalable business that can shift from 10 to 10k orders per week.

Start with the end product in mind.

Updated Anatomy of an Automated Business and Example of a Variable Profit Calculation coming soon!

How to: make the system the solution.

  • Contract specialist outsourcing companies (e.g., fulfilment / call centres).
  • Ensure that outsourcers are willing to communicate among themselves.
  • Give them written permission to make inexpensive decisions without consulting you.

Phase I: 0 – 50 units shipped (Do it all yourself).

  • Take all calls and emails yourself.
    • Write down FAQs.
    • Make pay per click advertisements and website more specific.
  • Personally pack and ship products to determine best / cheapest options.
  • Investigate merchant account options with a bank (esp. for card processing).

Phase II: >10 units per week (Outsourcing fulfilment).

  • Add the FAQ to your website and continue to develop it.
  • Find local fulfilment companies under “fulfilment services” or “mailing services”
TIP: call local printers and ask them for recommendations.
  • Limit to those with:
    • / negotiate no set up fees and monthly minimums (often smallest).
    • ability to respond to order status emails or phone calls from customers.
  • Ask for three customer references and ask those for examples of specific past issues.
  • Ask for net-30 terms (payment for services 30 days after rendered).
  • Have manufacturer ship directly to your fulfilment house.
  • Put fulfilment contact details on online “thank you” page and for order status questions.

Phase III: >20 units per week (Assembling an architecture of friends).

  • Research bigger fulfilment houses that also handle refunds and returns.
  • Ask for referrals to call centres and credit card centres they already work with.
  • Set up with credit card processor first (important for returns and refunds).
  • Review online vs. call split at testing and optionally test the call centres.
    • Call toll free numbers of some of their other clients.
    • Should be answered within 3 – 4 rings.
    • Any wait / on hold time should be < 15 seconds.
    • Ask difficult questions and gauge sales ability.

Minimise decisions and avoid complexity.

  • Offer one or two purchase options.
  • Offer one, fast shipping option and charge a premium.
  • Don’t offer over night / expedited shipping (too much headache).
  • Eliminate phone orders completely (online only).
  • Do not odder international shipments (customs are a pain).

Eliminate low profit and high maintenance customers (80/20).

  • See customers as equal trading partners.
  • Do not accept payment via Western Union, checks or money order.
  • Raise wholesale minimums to 12 – 100 units and require a tax ID.
  • Refer resellers to an online order form and never negotiate price on higher volumes.
  • Offer low prices products instead of free products to capture information.
  • Offer lose-win guarantees (“deliver in 30mins or it’s free”) instead of free trials.
  • Do not accept orders from common mail fraud countries (e.g., Nigeria).

Look bigger than you are when approaching large resellers or partners.

  • Use a mid-level title like “VP” or “Director” instead of “CEO” or “Founder”.
    • Makes the company look bigger than it is.
    • Avoids making you the obvious decision maker in negotiations.
  • Put multiple emails for different departments on your website even if they forward to just 1.
  • Set up an Interactive Voice Response (IVR) remote receptionist.
  • Do not provide a home address (use partner addresses or a PO box).

Finally, “Liberate” yourself physically and mentally.

Employees often struggle here because they fear taking control.

Escape the office.

Be smart about how and when you try to liberate yourself from the office.

  • Ask: If you don’t ask you don’t get.
  • Put yourself in your bosses shoes: adjust slowly and demonstrate benefits to them personally.
  • Time your requests for a period when it would be difficult to lose you.

Step 1: Increase your company’s investment in you.

  • Suggest a company funded training course.
  • Mention the benefits to your boss and the company.

Step 2: Prove increased output offsite.

  • EITHER: Call in sick but not Monday or Friday or it looks like a 3-day weekend.
  • OR: Use a preplanned project or emergency (family/personal issue, relocation etc…).
  • Request to work remotely: compromise on salary during that period if necessary.
  • Collaborate with your boss on how this will work to get them invested.
  • Work from home and double your output on those days in a traceable way.
  • Keep records of productivity for reference during later negotiations.

Step 3: Prepare the quantifiable business benefit.

  • Communicate ongoing remote working as business sense, not a personal perk.
  • Write bullets of quantifiable out of office results achieved (e.g., more hours billed).
  • Identify causes (e.g., no commute, fewer distractions out of office).

Step 4: Propose a revocable trial period.

  • Approach boss one week after absence.
  • Propose e.g., two days from home for two weeks (fall back to one day).
  • Use the evidence identified in step 3 to demonstrate value to business.
  • Make it clear the trial can be cancelled by your boss at any time.

Step 5: Expand remote time.

  • Repeat steps 2 and 3 on remote days (no need to call in sick).
  • Propose e.g., four days from home for two weeks (fall back to three days).
  • Ask for and address specific concerns if you come up against resistance.
  • Re-emphasise the revocable nature of the trial.

N.B., If a job is simply beyond repair, let go of it.

  • Don’t let your pride stand in the way of making the right decision now.
  • Being able to quit things that don’t work is integral to being a winner.
  • Investing a lot of time or effort into something doesn’t make it productive or worthwhile.
  • In any case, quitting is not permanent, the bills will get paid, it won’t ruin your benefits or resume.
  • Don’t forget to define the worst case: Is it really so bad? How could you mitigate it?.

Still struggling?

  • Imagine you had a heart attack: How could you work remotely for four weeks?
  • Put yourself in your boss’s shows: Would you trust yourself to work remotely? If not, why? Now fix it.
  • Practice environment free productivity. Work out the kinks before you go for liberation.
  • Quantify your productivity. These measures will help you and your proposal.
  • Practice getting past no e.g., be smart about timing, get specific conditions, look for precedent.
  • Remind yourself there are other options: post your resume to a job site under a pseudonym.

Replace binge travel with mini retirements.

There is a strong case for replacing end-of-life with frequent mini-retirements:

  • Physiologically: Energy and interest are cyclical, you wouldn’t / can’t batch all your meals at once.
  • Psychologically: It takes time (~2 – 3 months) to unplug and get perspective.
  • Emotionally: Relocation forces decluttering, simplification and prioritisation.
  • Financially: Relocation is much cheaper than both vacation and home life.

Mini-retirements are different from traditional escapes.

  • Vacations – one to six months of relocation vs. two weeks
  • Binge travelling – few/one vs. many locations
  • Sabbaticals – frequent and recurring (3-4 times / year)

Mini-retirements are not limited to those without children.

  • Take a trial run for a few weeks before an extended trip.
  • Use a week of language classes to help with transportation and making friends.
  • Use bribery and incentive schemes to keep children under control.

Four months out: Prepare mentally.

  • Take an asset and cash-flow snap shot.
  • Fear-set a one-year mini-retirement in a dream location in Europe.
  • Research starting points / region to begin exploring from.

Three months out: Eliminate.

  • Perform 80/20 on your belongings: Pack, store, sell, give away or bin.
  • Scout out travel insurance.
  • Prepare to rent, swap or sell your home.
  • Counter doubt/fear with “If I had a gun to my head how would I do it?”

Two months out: Automate.

  • Set up auto payments on reward point credit cards with regular billers.
  • Set up automatic direct debits for credit cards or any billers that refuse.
  • Set up online banking payees for any remaining billers.
  • Cancel all paper statements (and other bills).
  • Give a trusted member of your family and/or accountant power of attorney.

One month out:

  • Forward all mail to a friend / family member / personal assistant.
  • Get all immunisations for target region.
  • Set up software / processes needed for remote work.

Two weeks out:

  • Scan all identification, health insurance and credit/debit cards.
  • Give printed copies to family members and take a few of each with you.
  • Downgrade cell phone plan to lowest tier possible.
  • Set up email and voicemail autoresponders.
  • Do location level travel planning and book accommodation.

One week out:

  • Move remaining possessions out of your apartment.
  • Put digital copies of documents on a USB drive / upload to drop box.
  • Prep any automobiles for storage (tires, fuel stabilisers etc…).

On arrival:

  • Day 1: Take a hop-on-hop-off duty bus tour.
  • Take a bike tour of potential apartment neighbourhoods.
  • Buy an unlocked cell phone and SIM.
  • Email apartment owners or brokers (online, news papers).
  • Days 2/3: Find and book an apartment for one month.
  • Later: Eliminate extra things your brought but won’t use.

Book Crunch: “Meditations”, Marcus Aurelius

Meditations, Marcus Aurelius

Meditations, Marcus Aurelius

“Meditations”, Marcus Aurelius
Print length: 304 pages. Buy on Amazon.

Perfect for you if:

  • You wonder what kind of books Presidents and World Leaders keep by their sides.
  • You’re looking for new tools and practices to build into your daily life.
  • You’re new to Stoicism or “Meditations” is one of your favourite books.

“Meditations” is a collection of personal notes written by the author, Marcus Aurelius, to himself. These notes were never intended for publication and had two purposes:

  • To define for himself a life philosophy and ideal character worthy of aspiring to.
  • As an integral part of his struggle to live up to those two things.

In the process, Aurelius touches on some universal truths. Truths that still resonate with us almost two thousand years later.

The insights themselves are remarkable and inspiring but not unique. Instead, the power of “Meditations” is in both “Who” the author is and “How” they are written.

Who: Marcus Aurelius (121 – 180 AD) served as Roman Emperor from 161 – 180 AD. This is the age of the Imperial Cult. Roman emperors are divinely sanctioned authorities with almost limitless power and wealth. What’s more, Aurelius spent half (10 years) of his rule in brutal wars to defend the empire’s borders. Either factor was enough to drive many emperors to tyranny or madness – often both. Yet Aurelius’s humility and objectivity is staggering. He constantly reminds himself of his own mortality, insignificance and fallibility.

How: Just as impressive are the vulnerability, eloquence and pragmatism of Aurelius’s writing. It is philosophy without being philosophical. It is as accessible, quotable and practical. You can feel Aurelius’s struggle to make sense of the world around him. He repeatedly assaults the same themes, reframing them over and over. His striving reminds us that we all face the same journey though life, no matter who we are.

As a finished product Aurelius’s “Meditations” help us most obviously in two ways. They are:

  • As a long-term compass. An ideal that can point us in the right direction when we feel lost.
  • As a source of short term of inspiration. Providing reassurance, guidance and strength when most needed.

But the most important lessons from “Meditations” are not “What” but “How”. They are the daily practices we can bring into our own lives. Practices that help us define our own ideal and work through the obstacles to achieving it.

I bought several translations of “Meditations”. Many are free. The one linked above is not. It is, however, the best I have found. Gregory Hays keeps his translation as faithful to Aurelius’s original “Meditations” as he can. What’s more, he does so using clear and modern language that is easy and enjoyable to read. His introduction also gives fantastic context of the “Who” and “When” behind the work.

This crunch has three sections: Major Themes, Values to Live By and Practices to Start Today.

Major Themes

Aurelius revisits several themes throughout the “Meditations”. These include:

  • Impermanence: Aurelius reflects frequently on mortality. Human life is ephemeral and fleeting. Even the memory of it fades. Striving for fame or immortality in this life or after it is vain and futile. Instead, seize the present moment.
  • Cyclicality: Human nature stages the same play over and over through time and space – only the actors change. In particular, nature and its cycles of growth and decay are at the heart of many of Aurelius’s analogies.
  • Fate/Causality: Like stoicism, Aurelius’s take is one of Compatibilism (also known as soft-determinism). Our path is fated but we can choose to go with the flow or be dragged along with it (to the same end). Aurelius spends some time exploring this idea in the context of acceptance and resignation to external events (que sera sera). Disclaimer: this is a simplification – see Google for more detail.
  • Mindfulness: Perception begins with attention in the present moment to both the internal and the external. We cannot own the past or the future so it is pointless striving to hold on to them. Mindfulness also applies internally to our emotions and patterns of thought and behaviour. It is the first step in achieving…
  • Objectivity: A position we believe to be objective is often already intertwined with our reactions and beliefs. Making good decisions means identifying and separating raw perception from interpretation. This struggle is a frequent topic of interest for Aurelius. I would argue that each of the “Meditations” is itself an attempt to return to a place of greater objectivity.
  • Equality: Human nature is universal. We are all subject to the same drives and temptations. Aurelius reflects that under the same conditions, he is just as capable of any failing that he has observed in another. This insight is the foundation of understanding and patience.
  • Hierarchy: All men may be the same but that doesn’t make them equal. 10 – 15% of the Roman population have been estimated to be slaves. Aurelius draws several analogies to reconcile his views on equality with the hierarchical reality of the Rome he ruled (sun vs. rain, captain vs. crew, doctor vs. patient).
  • Civic duty / Justice: Aurelius does not believe in universal and inalienable human rights. He often reflects on the need for each citizen (including himself) to act for the good of the whole, even at individual cost. This view is more similar to a contemporary Chinese than American ideal.

Values to Live By

Throughout “Meditations” Aurelius lays out several values that he strived to live by.

They make for an inspiring read and a worthy goal for anyone to aspire to:

  • Balanced / moderate: opposed to extreme views and actions (especially in politics or religion)
  • Humble: having a modest estimate of one’s importance, accepting one’s own fallibility
  • Simple: doing only what is necessary, speaking clearly
  • Austere: not requiring comforts or luxuries; having a plain and unadorned appearance
  • Accepting: receiving people and happenings as they are without striving against them
  • Open: receptiveness to change or new ideas, especially in letting go of ones current beliefs
  • Diligent (esp. in planning): having or showing care and conscientiousness in one’s work or duties
  • Energetic: showing or involving great activity or vitality
  • Persistent: not giving up in the face of adversity, however great
  • Patient: able to accept delays, problems, or suffering without becoming annoyed or anxious
  • Pragmatic: dealing with things sensibly and realistically in a way that is based on practical rather than theoretical considerations
  • Mindful: consciously aware of internal and external circumstances in the present moment.
  • Purposeful: having or showing determination or resolve towards a defined purpose
  • Having integrity: the quality of being honest and having strong moral principles
  • Dispassionate (esp. in pain, in anger): not influenced by strong emotion, and so able to be rational and impartial
  • Silent (in thought, word and deed): ‘being’ over ‘doing’ or ‘having’, patience to observe clearly before acting, knowing when not to act at all and not drawing attention to oneself by ones actions
  • Rational: based on or in accordance with reason or logic
  • Cooperative: open and willing to be of assistance in working towards a common goal, working as part of a team
  • Forgiving: feeling no anger about or not wishing to punish offences, flaws or mistakes

Disclaimer: Defining values is a tricky business. These definitions combine dictionaries with my own interpretation of “Meditations” (and inevitable biases). I’m very open to improvements and suggestions.

Practices to Start Today

Referring to “Meditations” is like looking up answers in a textbook. It might let us know where we’re heading. It might even help us through a particular problem. What it won’t do is teach us to solve those problems by ourselves. For that, there’s no substitute for rolling up our sleeves each day and getting our hands dirty.

The most valuable things Aurelius gives us in his “Meditations” are not the answers. They are the tools that he used to solve the problems he faced. Like Aurelius, anyone can pick up those tools and learn to use them. Anyone can break and hone them, day-in-day-out against the challenges they face. We might not reach Aurelius’s level of mastery. We might not even come close. But we can all get closer.

  • Simplify: Despite being a Roman Emperor, Aurelius slept on a simple camp bed. He avoided rich clothes and shunned excess. Remember that everything you own ends up owning you. It demands your two most precious resources: time and attention. Simplify wherever you can. My own life never became happier than when I reduced its contents to a single 40 litre backpack.
  • Meditate (on paper). “Meditations” is the outcome of Aurelius’s greatest tool – making time each day to sit and think with a pen and paper. Do the same, even if you don’t feel emotional or overwhelmed. Think through the challenges you are facing. What are you sensing, thinking or feeling? What about the other people involved? Start by setting a timer for 15 minutes. Write whatever comes into your head. The only condition is that you cannot stop writing until the timer runs out. There is a kind of magic that goes on when we write by hand.
  • Define your values. Our values are at the core of personal meaning. Knowing them, and choosing to act consistently with them gives any “What” a “Why”. In the first ‘book’, Aurelius identifies the values that he cherishes most in those around him. He devotes the “Meditations” to working how to apply these values throughout his life. What would people say about you if you were to die tomorrow? What would you like them to say? What values inspire you in the people around you? Take time to reflect on these questions and think on paper. As you go through your day, try to act as if you already had the values you aspire to.
  • Reframe (“The obstacle is the way”). Whenever you come up against an obstacle think of it instead as an opportunity for growth. Better yet, consider that the obstacle might be part of an unconventional solution. They say that “there is no such thing as failure, only feedback”. Thomas Edison encapsulated this idea perfectly in his famous quip about the lightbulb – “I have not failed. I’ve just found 10,000 ways that won’t work”.
  • Practice Gratitude. It is impossible to feel jaded about the world around you when you are also grateful for it. Get started by writing just five things each day that you are grateful for on a piece of paper. You will be happier for it.
  • Surround yourself with great people. You are the average of the five people you spend the most time with. Aurelius could have surrounded himself with suck-ups and yes men. Instead he surrounded himself with people who loved him and inspired him to be a better person. Surround yourself with people who love you and inspire you to be a better person. Life is too short to fill it with destructive relationships.
  • Learn continuously. Aurelius’s early teaching was everything you would expect from a future Roman Emperor and he explicitly recommends sparing no expense for education. Despite his responsibilities as Emperor he continued to read widely and take extensive notes (much of the “Meditations” is filled with quotes from favourite authors). This dedication to life-long, continuous learning is clear throughout the “Meditations”.
  • Serve others. Despite almost god-like status, Aurelius’s never excluded himself from his own philosophies. In particular, his writings on civic duty make it clear that he saw himself first and foremost as a servant of his people. In this regard, he was among the few not corrupted by the power and wealth of his position. Serve others. It is one of the most rewarding things we can do and one of life’s greatest sources of meaning.

Further Reading

“Letters from a Stoic”, Seneca – the original blog on Stoicism. Seneca’s letters to his friends are full of good, practical advice. His thinking and writing would come to influence Aurelius some 100 years later.

“Discourses and Selected Writings”, Epictetus – A bit harder to read than other books on this list but an excellent primer on all things Stoic.

“Man’s Search for Meaning”, Viktor Frankl. One of the greatest books of the modern age. Short, readable and powerful. Its insights are as profound as its subject matter is heart breaking. You can find my book crunch here.

“The Obstacle is the Way”, Ryan Holiday – Holiday is the most prolific and outspoken of the 21st Century’s “New Stoics”. “Meditations” is one of his top books and Aurelius’s fingerprints are all over his work. His books are both readable and powerful – this one is a good place to start.

The Daily Stoic, blog – one of today’s best source for all information related to Stoicism.


TANQ entries for “Meditations”

TANQ is WhyWhatHow’s growing central library of thoughts, anecdotes, notes and quotes.

The happiness of those who want to be popular depends on others; the happiness of those who seek pleasure fluctuates with moods outside their control; but the happiness of the wise grows out of their own free acts.

Marcus Aurelius Meditations

“Do external things distract you? Then make time for yourself to learn something worthwhile; stop letting yourself be pulled in all directions.”

Marcus Aurelius Meditations

“You could leave life right now. Let that determine what you do and say and think.”

Marcus Aurelius Meditations

“You need to avoid certain things in your train of thought: everything random, everything irrelevant. And certainly everything self-important or malicious.”

Marcus Aurelius Meditations

“Never regard something as doing you good if it makes you betray a trust, or lose your sense of shame, or makes you show hatred, suspicion, ill will, or hypocrisy, or a desire for things best done behind closed doors.”

Marcus Aurelius Meditations

“Forget everything else. Keep hold of this alone and remember it: Each of us lives only now, this brief instant. The rest has been lived already or is impossible to see.”

Marcus Aurelius Meditations

“Nothing is so conducive to spiritual growth as this capacity for logical and accurate analysis of everything that happens to us.”

Marcus Aurelius Meditations

“The things you think about determine the quality of your mind. Your soul takes on the colour of your thoughts.”

Marcus Aurelius Meditations

“True good fortune is what you make for yourself. Good fortune: good character, good intentions, and good actions.”

Marcus Aurelius Meditations

“Practice really hearing what people say. Do your best to get inside their minds.”

Marcus Aurelius Meditations

“It never ceases to amaze me: we all love ourselves more than other people, but care more about their opinion than our own.”

Marcus Aurelius Meditations

Book Crunch: “Perennial Seller”, Ryan Holiday

Perennial Seller, Ryan Holiday

Perennial Seller, Ryan Holiday

“Perennial Seller”, Ryan Holiday
Print length: 257 pages. Buy on Amazon.

Perfect for you if:

  • You’re a creator – be it writer, film maker, musician, artist or entrepreneur.
  • Many of the things you love, read, listen to, watch or use are over 10 years old.
  • You want to understand why some creations become timeless sellers.

perennial | adjective lasting or existing for a long or apparently infinite time; enduring or continually recurring.

Ryan Holiday’s “Perennial Seller” is a book for creators that explains how to build for timeless and enduring impact. It serves as a refreshing reminder of long term value in an age where many industries (and governments) seem so fixedly short-termist. True to its title, the book favours time-tested, practical and inspiring home truths over get-rich-quick hacks.

I learned a huge amount from reading it and am looking forward to applying its principles in my own writing. I will certainly be re-reading it and these notes again in the future.

The book divides into two main parts. In Part I: “Making a Perennial Seller”, Ryan describes what it takes to create in a way that withstands the tests of time. In Part II: “Marketing a Perennial Seller”, Ryan explains both how to ensure your message is heard and also why it is important be personally at the centre of the marketing process.

Ryan’s own extensive reading and network is evident in the number of powerful examples and quotes throughout the book. These help to add an enduring sense of depth and credibility to his arguments.

If you love reading and/or don’t know of Ryan’s work I strongly recommend a visit to his blog and signing up for his excellent monthly reading list. I’ll be crunching many of the books that appear on it in the coming months.

“Perennial Seller” is available on Amazon in both kindle and paperback editions.

Part I - Making a Perennial Seller

Start with the right attitude.

There is no magic to creating perennial sellers,

  • Masterpieces are made layer by layer, piece by piece …
  • … and ‘genius is 1% inspiration and 99% perspiration’.

But creating a perennial seller must be your aim from the start,

  • Aim for lasting (> 10 years) impact and relevance.
  • Harden yourself to short-term measures of success.

And you must prepare to meet the demands of delivering massive value.

  • Laser-like dedication (and by extension sacrifice),
  • Persistence (fuelled by a clear personal motive), and
  • Dogged end-to-end personal responsibility (from making to marketing)

Develop specific positioning.

One sentence, one paragraph, one page
This is a [ What ] for [ Who ] that helps them by [ How ]

Create something defined and accessible… [ What ]

  • Know your genre conventions and audience expectations.
  • Be bold and experiment with breaking its conventions.
  • But not too many at once, it must stay accessible.

… that addresses a specific core audience… [ Who ]

  • Picture creating for just one specific person.
  • Create for your core audience only, crossover is a bonus.

… and solves a significant and enduring problem. [ How ]

  • If the problem is not significant, why should people care?
  • If the problem is not relevant in 10 years, nor is the solution.

Create, evolve and refine until perfect.

Concept > Prototype > Draft(s) > Refined creation

Start small – testing early and often.

  • Grow from e.g., concept to conversation to article to talk to book.
  • Test for external resonance and feedback at each stage.
  • Change and pivot early in response to feedback.

Next, write the first draft.

  • Consider a pre-rest/drawdown period to prepare physically and mentally.
  • Then create intensively and with your audience of one always in mind.
  • Make time and space to focus on nothing else during this period (see Deep Work).

Now, prepare for extensive rewriting, editing and refinement.

  • Understand that this process is usually as long or longer than the writing.
  • Seek feedback externally – from editors and audience members you trust.
  • Be open to feedback, even if it’s major – many classics are total rewrites of their first draft.
  • Keep iterating, even after release – many classics only peaked in later editions.
  • Keep the positioning specific (even if it needs updating) and stay resolute to your aim of longevity.

Part II - Marketing a Perennial Seller

Word of mouth sustains life, marketing creates it.

The Lindy effect: The chance of something disappearing decreases the longer it exists.

Word of mouth is the self-sustaining heartbeat of a perennial seller.

  • It passively refreshes discoverability in the absence of active marketing.
  • It converts better (50x so for trusted and emphatic vs. low quality word of mouth).
  • It feeds on and multiplies itself.

To qualify you must first deliver massive value (see Part I).

But even then, you must make yourself heard.

  • There is more competition for our limited attention than ever before.
  • A creation must stay above this noise or disappear into it – no matter how good it is.
  • Marketing brings a creation momentarily to the surface and gives it a chance at life.

You must take personal responsibility for driving discoverability and building a platform.

Many shy away from marketing.

  • To distance themselves from judgement/failure.
  • Because they prefer creating.
  • Out of purist sensibilities.

But you cannot outsource it, nor should you want to.

  • Nobody cares about your creation as much as you do.
  • Nobody understands the positioning as well as you do.
  • Giving up control means leaving everything you’ve worked for to chance.

Your job is to tell people what your creation is and why they should care.

  • Marketing is anything that gets and keeps customers.
  • Its goals are to drive short term discoverability and build a long-term platform.

Driving discoverability is a sprint: it is creation specific and has diminishing returns.

Concentrate on a launch day.

  • Bring relationships, media contacts, past experience, favours, budget and allies to bear.
  • Choose a date with a hook (e.g., international XYZ day).
  • Use this spike to puncture through the noise.

Give things away for free.

  • Sacrifice short-term profit for discoverability (often cheaper than you think).
  • Create a core following by giving away the first X units for free (e.g., as samples or to influencers).
  • Give part of your service away for free to drive sales in others (e.g., free TED videos vs. $10k USD conference tickets).

Use discount pricing.

  • Price for accessibility and discoverability – don’t let ego stand in the way of impact.
  • Use occasional short-term price drops to drive sales. Often has a prolonged impact.

Find your champions.

  • Find, engage and prefer organic, existing users of your creations over paid influencers.
  • Consider non-traditional influencers (e.g., business figures or politicians over celebrities).
  • Offer don’t ask: help them, send free things (enough to give away to their friends).

Be wary of traditional media.

  • Can be useful as part of a larger campaign by building a profile and credibility.
  • But rarely gives a good direct return on high cost of time and money.

If you still want it: Start with smaller, niche outlets.

  • They appeal directly to your target market (remember Positioning).
  • These are cheaper and easier to access than major publications …
  • … and also create momentum by feeding into them anyway (like tributaries into a river).

Even then: Don’t pay for attention. Earn it. Try:

  • News-jacking. Adapt quickly to and piggy back on ‘hotter’ trends (e.g., accepting bitcoin payments).
  • Creative advertising. Attention grabbing but risky for big corporates and so often overlooked and under-competed for.
  • Publicity stunts. Give reporters something to write about. Be bold (but not too bold).
  • Being direct. Google reporter contact details. Call them. Make it interesting by being interested.

For everything else (e.g., social media) adapt, test widely and double down on results.

  • Adapt to the channels available at the time (this changes rapidly).
  • Adapt to the features and popularity of those channels (changes even more rapidly).
  • Try a bit of everything. See what sticks. Double down on it.

Building a platform is a marathon: it benefits all your creations and is compounding.

A platform is all the tools, relationships, access and audience you have to spread creative work.

Building a direct (e)mailing list by providing massive value.

  • Give something free – an ebook, a sample, a service (e.g., book recommendations).
  • Run competitions and sweepstakes – make the free offer time-limited.
  • Do things by hand – create a physical form you can hand out at events.
  • Do a swap – Cross promote with another creator’s list.
  • Make it easy – Use pop-ups and simple sign up forms, put a link in your email signature.
  • Ask your existing contacts to join – export your social network followers, ask family and friends.

Build a karma positive network (contacts, relationships, influencers and fans).

  • Never dismiss anyone – rule #1 is just be a nice person.
  • Play the long game – all senior decision makers were once fresh faced minions.
  • Focus on pre-VIPs – engage people who should be famous, even if they’re not yet.
  • Participate – honestly and authentically with your network and fans (see rule #1).
  • Be a giver – give long before you think of receiving. Always stay karma positive (See Give and Take).

Build a body of work.

  • Good work compounds itself – the more value you deliver, the wider your platform will grow.
  • Which is why making is also marketing – building a platform is part of building a career as a creator.

Reach out to new fans.

  • Collaborate with other creators to make something new that promotes crossover.
  • Create variations on your portfolio that expand as well as serve your current audience.

Build an empire. Ask yourself:

  • What new areas would my expertise be valuable in?
  • Can I cut out the middleman and invest myself?
  • Can I help other creatives achieve what I have?
  • What are people in my field afraid of/looking down on?
  • How can I diversify my income stream?
  • What would I do if I took a break from creating?
  • What components around my work can I improve or grow?
    (e.g., live events, conferences, subscriptions, memberships)

Related Reading / Watching / Listening

“How Great Leaders Inspire Action”, Simon Sinek: The structure of this 20 minute TED talk bears striking similarities to Ryan’s book. It was also the inspiration for the title of this blog.

“How I Built This” , NPR: Is a podcast about innovators, entrepreneurs, and idealists, and the stories behind the movements they built. A fascinating insight into the stories of some of today’s Perennial Sellers.

“Give and Take: A Revolutionary Approach to Success”, Adam Grant: This wonderful perennial seller is a fascinating insight into the network building power of becoming a giver rather than a taker.

“Shoe Dog: A Memoir by the Creator of NIKE”, Phil Knight: A fascinating and candid memoir from one of the 20th Century’s greatest entrepreneurs and perennial creators.

“Steve Jobs: The Exclusive Biography”, Walter Isaacson: As above.

“Elon Musk: How the Billionaire CEO of SpaceX and Tesla is Shaping our Future”, Ashlee Vance: And again. See also this excellent series of posts from Wait but Why.

TANQ entries for “Perennial Seller”

TANQ is WhyWhatHow’s growing central library of thoughts, anecdotes, notes and quotes.

“A book should be an article before it’s a book, and a dinner conversation before it’s an article. See how things go before going all in.”

Ryan Holiday Perennial Seller

“You don’t have to be a genius to make genius – you just have to have small moments of brilliance and edit out the boring stuff.”

Ryan Holiday Perennial Seller

“The best way I’ve found to avoid missing your target – any target – entirely is to identify a proxy from the outset, someone who represents your ideal audience, who you then think about constantly throughout the creative process.”

Ryan Holiday Perennial Seller

“The key to success in non-fiction work [is] that the work should either be ‘very entertaining’ or ‘extremely practical'”

Ryan Holiday Perennial Seller

“The higher and more exciting standard for every project should force you to ask questions like this:
– What sacred cows am I slaying?
– What dominant institutions am I displacing?
– What groups am I disrupting?
– What people am I pissing off?”

Ryan Holiday Perennial Seller

“People want things that are really passionate. Often the best version is not for everybody. The best art divides the audience.”

Ryan Holiday Perennial Seller

“Write out exactly what your project is supposed to be and to do in …
One sentence.
One paragraph.
One page.
This is a ___ that does ___. This helps people ___.”

Ryan Holiday Perennial Seller

“When it comes to attracting an audience, the creators who take the time to get their positioning and packaging right – who don’t just go with their first instinct and hope – are the ones who will win.”

Ryan Holiday Perennial Seller

“Nothing has sunk more creators and caused more unhappiness than this: our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.”

Ryan Holiday Perennial Seller

“Luck is polarising. The successful like to pretend it does not exist. The unsuccessful or the jaded pretend that it is everything. Both explanations are wrong.”

Ryan Holiday Perennial Seller

4 Years and 6 Languages Later: The Ultimate Language Learning Guide

How to Learn a Language

How to Learn a Language

Perfect for you if:

  • You want to learn a new language but don’t know where to start.
  • You’re already learning a new language but want to speed it up.
  • You think English is all you need or you’re “not a language person”.

Learning a new language is one of life’s most misunderstood challenges. It is also one of its most rewarding. A new language is a gatekeeper to new people, places, knowledge and experiences. It is a passport to a country that we didn’t even know existed.

I’ve spent most of my life learning languages – either because I had to or because I wanted to. I was raised bi-lingual (English/French) and studied French, Latin and ancient Greek until I was 16. In the last few years, I’ve raised German to fluency and Mandarin, Russian and Spanish to somewhere between fluency and conversational.

This guide doesn’t claim to be the best or only way to learn a language. Instead, it’s a collection of my own experiences and mistakes, plus a few pointers and tools. Things, in short, that I wish I’d known about much earlier. I hope you find something in it that gives you the confidence or push to start or accelerate your own language learning journey.



  1. Myth 1: English is Enough
  2. Myth 2: The ‘Language Person’
  3. Myth 3: I’m Too Old to Learn a Language
  4. What is Fluency?
  5. How Long Will it Take?
  6. Languages: by frequency
  7. Languages: by difficulty

3 Factors for SuccessContents

There are three factors that determine language learning success: Mindset, Motivation and Practice. I’ll lay out some practical tips for each in this guide but for now I’ll define what I mean.


The most important mindset to develop is that anyone can learn a second language. Don’t believe me? Ask anyone in Germany under 25 and they’ll tell you (in perfect English). Still sceptical? Take my word for now that ‘language people’ are not born, they are created.

The second most important mindset is that making mistakes is essential to learning. I once called my Chinese homestay family’s dog a prostitute for an entire evening. I also remarked to a group of Germans that my face, after a run, was covered in poo (instead of sweat). If you want to learn a language you are going to need to make a lot of mistakes. And that’s more than ok it’s essential!


Language learning isn’t quick and it isn’t easy. There will be ups and downs. Highs and lows. Frustrations and breakthroughs. After the initial rush of quick progress comes the long slog to fluency and mastery. Learning a language requires persistence. Motivation is its fuel.


Finally, it helps to remember that language learning is a skill. Like all skills, progress is a factor of quantity of time and quality of practice. There are no magic shortcuts. You wouldn’t expect to jam fluently on a guitar after three weeks (or even three months) – don’t expect to learn a language any faster.

The role of good training tools and strategies is not to cheat the system. It’s to avoid the journey taking longer than is necessary.

The Anatomy of LanguageContents

All languages have the same basic structure. Knowing it will help throughout this guide and the rest of your learning journey.

Each language breaks down into three theoretical skills:

  • Pronunciation
  • Grammar
  • Vocabulary

The relative difficulty of each theoretical skill varies from language to language. Mandarin grammar is much easier than Russian grammar. Pronunciation and vocabulary are a different story. For more on relative language difficulty see the appendix.

There are also four practical skills:

  • Speaking
  • Listening
  • Reading
  • Writing

Understanding (listening, reading) is easier than creating (speaking, writing). The amount of time you’ll need to put into each practical skill will vary by both language and personal goals.

Setting Language Learning GoalsContents

A clear vision and defined goals will keep you on track and motivated during the hard parts of your language learning journey.

Decide on a vision

Take out a pen and paper and ask yourself why *you* are learning *this* language. Is it for love? Out of necessity? For an upcoming trip?

Now consider the four practical language skills. What level do you need to reach in each to make this vision a reality? The definitions given by the Common European Framework of Reference (CEFR) may help. You can find these in the appendix.

Make a plan

Now we have a rough idea of where we need to get to (and why) let’s make those goals more concrete. To do this we need to make them SMART (Simple, Measurable, Actionable, Realistic and Time Bound). Ask yourself “what specific thing can I do/achieve to show that I have reached the level I am aiming for?”.

Some examples of SMART goals might include:

  • I make a 15-minute speech to 10 people by dd.mm.yy,
  • I read 5 books cover to cover by dd.mm.yy; or
  • I write an article for a local paper / journal by dd.mm.yy
  • I pass XXX exam by dd.mm.yy

N.B., Passing an exam is (on its own) a terrible reason for learning a language. But in the context of a broader motivation exams can be a part of a very SMART combination.

Once we’ve set a clear goal it’s time to work backwards from it and determine what needs to happen when to get us there. What are the main barriers we face? Why aren’t we already at our goal? What/who do we know that can help us get there faster?

If the goals we’ve set are more than 3 months away it can be helpful to break them down into shorter milestones. The only way to eat an elephant is piece by piece.

Get it done

Goals give us our “why” – they are a powerful source of motivation. But sometimes they can feel so daunting that we end up procrastinating to avoid them.

When this happens, here are two great life hacks that can help us get back on track.

First: ask “What is the very next action I can take to make some progress towards this goal?”. It could be looking at a single website, asking a question or downloading a new app. Keep it small, write it down now, tick it off. Rinse and repeat. Sometimes all it takes to regain momentum is a little push.

Second: switch your focus to process instead of product. Commit to making whatever progress you can in the next 25 minutes. Then have a 5-minute break. Then repeat. Process goals are a great way to bring us back to the present moment and break big goals into manageable chunks (see the Pomodoro Technique).

Practical Tools and TipsContents

The single most valuable tip I can share with you is to learn how to learn. There are many fantastic language learning guides and books out there. Read some. A small time investment up front could save you years of frustration down the line.

In the meantime, here are some general tips on:

As well as specific tips on:

  1. Pronunciation
  2. Grammar
  3. Vocabulary
  4. Speaking
  5. Listening
  6. Reading
  7. Writing

Where to focus your time and energy

Focus 1: Speak from the very first day. One-on-one with a local is preferable (see below for tips). Book your first lesson even if you only know 5 words.

Speaking early helps you progress faster and keeps you motivated. One of the greatest things about languages are the people you meet and new friends you make along the way.

Focus 2: Pronunciation, grammar and vocabulary. Early focus here will pay big dividends later on. Pronunciation, in particular, is very difficult to reverse and correct once in place.

Focus 3: The remaining three practical skills: listening, reading, writing. As you advance it is more interesting (and fun) to learn a language as naturally as possible. Which of these you focus on will depend on your goals and preferences.

Start shifting time to these practical skills when your vocabulary hits the ~1,000 word mark. By this time you should also have a good few weeks or months of speaking and grammar under your belt.

N.B., No matter what level, speaking and vocabulary learning should always stay an important part of language learning.

Spaced Repetition Systems (SRSs)

Spaced Repetition Systems (SRSs) are hands down the quickest way to learn almost anything and make it stick.

The premise is simple. Imagine a basic paper flashcard with a question on one side and an answer on the other. It turns out that that the perfect time to review that flash card is the exact moment you’re about to forget it. SRSs handle this scheduling for you but for thousands of flashcards at a time. Unlike paper, they also let you include sound files, photos or even movies on the flashcards you create.

My personal favourite SRS is Anki – it’s free and the algorithm is excellent. Its customisability means you can use it to learn almost anything fast – from science to history of art. Gabriel Wyner’s “Fluent Forever” is my go-to on using Anki to learn languages.

There are plenty of alternative systems out there that are well built and user-friendly. These include Rosetta Stone, Memrise and Duolingo. In my opinion, Rosetta Stone doesn’t offer value for money. The latter two are great free options for beginners or dipping a toe into a new language. In the long run, they lack the power and flexibility of Anki that will become important to you as you advance.

More Useful Websites and Tools

Aside from Anki (and other SRSs) there are hundreds of great language learning websites, apps and tools on the internet. Many are general, some of them are language specific. Amazingly, most of them are totally free.

Here is a shortlist of the non-language-specific tools which I use on an almost daily basis. Know of another great tool? Suggest it in the comments below. I may have tried it and opted for something else but the chances are I may not know about it!

iTalki – The single best place to find a one-on-one language teacher online at the fraction of the cost of a language school. Benefits include:

  • Free membership
  • Three levels of teaching: language partner (free), community and professional
  • Quick and simple search to find a user rated teacher by location, gender etc…
  • Simple scheduling system
  • No currency issues
  • Free native speaker corrections to any writing you upload within ~48h

Lang-8 – As with iTalki I use Lang-8 as an alternative place for quick and community-driven writing corrections. Also free.

Forvo – An amazing free repository of recordings by native speakers for almost any word in any language. If they don’t have what you’re looking for you can request it. A member of the community will usually fill the gap within 48h. Almost every flash card I create contains one or more Forvo recordings.

Rhinospike – Like Forvo but aimed at on-demand requests for longer texts and passages. You can speed up the process by recording someone else’s request for them. Also free.

WavePad – Mac only. Superb for breaking up long audio files into smaller chunks. The home version of the software is free to use.

Skype – Still the easiest and most common platform for online conversations. Perfect for language e-lessons. Google will help you find a plugin to record your sessions.

Google Images – An amazing insight into the collective visual consciousness of the internet. Search on the Google images that’s local to your target language for extra insights.

YouTube – Great for music, T.V., programs and even grammar explanation videos. Other languages (especially Mandarin) may offer other alternatives.

Spotify – Perfect for creating foreign language music playlists and taking them on the go (premium version only).

Google Translate – Responsible for hilarious sign, t-shirt and restaurant mis-tranlslations the world over. Perfect for a quick check but use with caution.

1. Pronunciation

In theory

Pronunciation is an important part of sounding like a local (in Mandarin, it’s essential to even get by). In any case, once learned, pronunciation is hard to change. This is one reason an upfront investment is very worthwhile.

Pronunciation begins with phonemes – the distinct units of sound that distinguish words. English has 44 phonemes, for example, p, b, d, and t in the words pad, pat, bad, and bat. Other languages have their own sets (Hawai’in has 13 whilst Taa has 120!) and the degree of overlap between them varies.

As babies we can hear the full possible range of phonemes. The problem is that as children we forget to hear the phonemes that aren’t in the languages we speak. It’s actually less like forgetting and more like specialisation. This lets us differentiate the sounds of these languages even under heavy distortion.

It is very difficult to pronounce words if you can’t hear the sounds that create them. It also makes it harder to hear and memorise them. This is why relearning phonemes helps both pronunciation and speeds up learning.

In practice

Here are some ways to practice phoneme recognition and pronunciation:

  • Practice phoneme recognition through minimal pair differentiation. I use Fluent-Forever’s pronunciation trainers combined with Anki.
  • Mimic and get feedback from native speakers. Ask your teacher or your friends. Practice copying your favourite film or T.V., personality.
  • Record yourself and compare it with native recordings (see Forvo). Adjust and repeat.
  • Learn to sing in your shower or through private lessons. This also provides a great insight into a language’s culture and is an amazing way to impress new friends! YouTubeSpotify or your favourite music streaming service are perfect for this.
  • Use back-chaining to tackle difficult words. When learning to pronounce a new word, start with the last syllable and work backwards. Try it – this tip is worth its weight in gold.
  • Avoid group classes. In a group class of 4 people (plus a teacher) you spend ~80% of the time hearing incorrect pronunciation. See speaking tips for more information.

2. Grammar

In theory

Grammar is the framework supporting an entire language.  It is the key to turning 1,000 words into 100,000 sentences. It unlocks whole new ways of self-expression in every next conversation. As a means to an end, grammar is not only essential, it can even be exciting (you may have to trust me on that)!

Sadly, teachers with many students have no choice but to focus on the theoretical parts of language. The problem is that, in isolation, grammar is a soul-destroying way to learn a language. This is one reason why classrooms are such terrible places to learn them.

One of the reasons that grammar is so daunting to tackle is that it is almost a language in itself. From prepositions, cases and tenses to aspects, pronouns and participles – it’s easy to get lost. The important thing to remember is that everyone goes through this double learning curve – it’s OK to be confused!

The good news is that, once learned, grammar turns out to have only a few, simple concepts. What’s more, these concepts are mostly consistent between languages. This is one of the reasons that picking up a third or fourth language is often easier than mastering a second.

In practice

There are few better ways to make quick progress in a language than starting with a good grammar book. Here are a few tips for giving grammar a second chance:

  • Buy a good grammar book. Don’t buy the biggest grammar book you can find. Instead, start with one specific to your language level and upgrade as you go along. A good book will stay practical, introduce you to useful vocabulary and be full of exercises. Ask the internet or your teacher for language-specific recommendations.
  • Work through the grammar book. Add new structures and vocabulary to your SRS.
  • Do the exercises given in each chapter. Add any that you get wrong to your SRS.
  • Be patient with yourself. Starting off with grammar means learning two languages in parallel for a while!
  • Read and write as often as possible. Reading will expose you to thousands of natural language grammar examples. Writing will help you be sure you’ve internalised all the grammatical principles.

N.b., applications like Duolingo are not a one-stop shop. They are great for vocabulary but terrible for grammar. Nothing beats a good grammar book.

3. Vocabulary

Words are the building blocks of language and it always pays to invest time in expanding your vocabulary.

As you start out, you’ll come across many new words in your lessons and grammar book. As you improve, listening and reading will also become important sources of new words. Here are some tips when adding them to your SRS:

  • Avoid translations by using pictures wherever you canAvoid the fluency destroying habit of translating between languages in your head. Instead, link words to mental images and concepts. Use Google Image in the target language (e.g., Google.ru for Russian).
  • Learn words as part of phrases or sentences to strengthen connections between words. Many dictionaries will provide example sentences for a given word.
  • Include a recording from a native speaker. Forvo is a great place to find or request these for free.
  • Use definitions in the target language where pictures won’t do. Switch from a bilingual to a monolingual dictionary when able.
  • Learn adjectives as antonym pairs. If you add ‘big’ to your SRS then also add ‘small’.

It’s important keep active in learning new vocabulary. As a beginner, being systematic in your approach will help fill any important gaps. Active learning becomes especially important when approaching day-to-day fluency. At this point it can be tempting to stick to what you know. This feels good but cripples further progress.

Here are some sources to keep you busy throughout your language learning:

  • Cognate lists. Ask Google for yours. Cognates are words that are very similar between two languages. These lists can help you learn hundreds of words in a very short time.
  • Glue words. Common words that supercharge sentence building and are worth learning up front. Here’s my list.
  • Frequency dictionaries/lists. Googling some variation of ‘500 most common words in XXX’ is a good place to start.
  • Thematic dictionaries/lists. Perfect for drilling down into a particular topic. My favourite for European languages are the ‘Using French / German / Spanish Vocabulary’ series.
  • Vocabulary trainers. For example Glossika which has 3,000 sentences (with native recordings) translated across many languages. This is great for practicing multiple languages at once.

One final tip that I’ve read about but never used is ‘Labelling’. Put post it notes on every object in your house with its name in your target language. The only prerequisite to easy vocab learning is an understanding family or flat mate!

4. Speaking

Book your first language lesson the very first day you decide to learn a new language. Even if you only know 5 words. Speaking will keep you challenged. It will keep you motivated. It will make you new friends. It will teach you about culture. It will help you learn about great resources specific to your language.

The longer you put off speaking a language the longer it will take you to be able to speak it. This is true even if you’ve spent years studying grammar or watching TV shows in your target language.

This suggestion comes with two caveats:

  • Never attend a group sessions.
  • Never use a language school.

In a group lessons you will spend the majority of your time listening to other people’s mistakes. With a language school you will pay up to 10 times what it would cost you to go direct. This is twice as true for third party immersion programs.

Learning a language online

These days it is both easy and affordable to find one-to-one tuition for any language online. One of the best services for this is the iTalki community.

I tend to use community teachers at a cost of 5 – 10 USD per hour. This works for my lifestyle and budget but there are great options on either side of this to suit any needs.

Tips for online language learning

Here are a few tips after learning five languages and spending hundreds of hours online:

Booking the sessions:

  • Interview as many teachers as you need to until you find a few that feel ‘right’. Book 30 minutes trial sessions for this.
  • Start with many 30 minute sessions. They will exhaust you. Progress to fewer 60 minutes sessions as you improve.
  • Use many teachers. Male and female, of various ages and from different regions. This will give you much broader exposure to all the nuances of a language.

During the sessions:

  • Stay in your target language. At all times, even when it’s frustrating. Replace teachers that switch to English.
  • Vary the lesson theme. Avoid talking about the same things again and again. This feels good but is an illusion of confidence. Push yourself to discuss and role play new scenarios or themes.
  • Record and review the session audio. Ask permission first. Pay attention to pronunciation and vocabulary.
  • Ask the teacher to type any new words or corrections during the session. Then add them to your SRS.
  • Avoid video for >50% of your sessions. This is harder but will make you a much better speaker in the long run.
  • Degrade the audio quality. More advanced. I loop the sound of a busy train station in my ear during some lessons. This replicates the noisiness of real life situations.

Preparing for your first lesson:

  • Prepare an introductory script in your own language. Translate it with Google and then use and correct it in your first session.
  • Use Google translate to help you get your point across.
  • Ask lots of questions. Most of my best language resources have come from my language teachers. You can also ask all sorts of personal / cultural questions you might otherwise be afraid to!
  • Don’t worry about making mistakes! Your teachers are there to help you not judge you.
  • Don’t forget to have fun!

Learning a language in person

It is very possible to become fluent in a language without ever visiting a country that speaks it. Not sure where to start? Here are a few real-world ideas to get you going wherever you are:

  • Attend language exchange events. Look on Google, FaceBook, Couchsurfing or the events boards at language schools.
  • Attend cultural events. Go to a Salsa or Italian cooking class. Look at the event calendar on a country’s embassy website.
  • Eat in foreign restaurants and strike up a conversation with the waiting staff there.
  • Host foreign guests at your home via e.g., Couchsurfing or AirBnB.
  • Talk to strangers. Asking someone where they’re from in their own language is a great way to start a conversation.
  • Talk to yourself. Label or describe everything around you. Keep a note of missing vocabulary to tackle when you get home.

And a few more for when you finally get to enjoy immersing yourself in the target country:

  • Practice in taxis. This is one of the best ways to get cheap conversation practice from an eclectic mix of people.
  • Attend local Couch Surfing meet ups and hang outs. Find them on the Couchsurfing website and app.
  • Stay with locals via e.g., Couchsurfing or AirBnB.
  • Meet up with iTalki teachers or language exchange partners. These experiences may turn out to be some of the most surprising and rewarding of your life.
  • Engineer real life scenarios. Negotiate at the market but don’t buy anything. Try buying a train a ticket then pretend you forgot your wallet etc…

Finally, here are two tips to make the most of these situations when you’re in them:

  • Stay in your target language. Avoid the strong temptation to switch to English. Be stubborn about staying in your target language if they do. This can be hard in places where many people speak English well but is worth the effort.
  • Pay attention to non-verbal cues. There’s more to becoming a local than the way you speak. Pay attention to cultural and non-verbal cues. How do people stand? dress? use facial expressions?

5. Listening

The advantage of listening is that you don’t need to do anything with your hands. This makes it great for those times when you’re running, driving or similarly engaged.

Speaking from day one means you’ve been getting plenty of listening practice in right from the start. Here are a few more ways to take your listening skills to the next level when you’re solo:

  • (Language Learning) Podcasts – usually free and interesting. You can also usually control playback speeds which is helpful!
  • Audiobooks – with and without a companion physical book
  • TV shows – with and then without subtitles (first translated then in target language)
  • Films – as for TV Shows. Does anyone else remember Muzzy?
  • News recordings – slowed then full speed.
  • Music – read the lyrics before hand and/or during if you can
  • Custom recordings – see Rhinospike
  • Audio only/mainly language courses – like The Michael Thomas Method (not my favourite)

Many of the best sources are language specific – ask your teachers, friends and Google for help finding them.

To really give your brain a stretch try the above but with the following twists:

  • Degrade the audio. Reduce the quality of the sound file or play ambient background noise (like a busy street or train station) while you’re listening.
  • Summarise or paraphrase (verbal/written) what you’ve heard once you’re done listening. Discuss it with or explain it to a friend or the iTalki community.
  • Transcribe what you’re hearing as you hear it – this is also a great way to practice writing.

N.B., Some people will claim to be able to teach you a language subconsciously (e.g., during sleep). These methods are not worth the time or money invested in them. Learning requires focus, energy and time – if it feels laughably easy, you’re not learning.

6. Reading

As you hit the thousand word vocabulary mark it’s time to start reading in your target language. Here are just a few reasons why reading is my favourite approach for natural language acquisition:

  • Passive exposure to thousands of grammar structures
  • Passive exposure to new and old vocabulary – You learn ~600 new words per book. Not to mention the common words you’ll be revising.
  • Insight into your target language’s history and culture – especially its turns of phrase and idioms.
  • Learning (about something else) whilst you learn – two birds with one stone!
  • The chance to discover new authors and rediscovering old ones
  • A more faithful retelling of a story than any translation

I love a paper book but I’m going to let you in on a secret: for reading in a foreign language Kindles are a game changer. Why? The simple tap-to-translate dictionary system. That and you can buy and carry a thousand books in almost any language right in your pocket. (I’m sure other eReaders might also work I just haven’t tried them).

Whether you opt for an eReader or paper book the next question is what to read. My recommendation is to start with familiar stories, translated into your target language. For example, I always start with the first three Harry Potter books. Why? Because they’re easy to read and I know the story. This added context makes it much easier to work out what’s going on if(/when) I get stuck!

The first page might take you 6 hours to read, but the second will take 4 hours, the third 2 hours and so on. Stick with it. Before you know it you’ll be powering through and supercharging your language learning.

As soon as you are able, move on to easy books written in your target language. This not only improves your language skills but also exposes you to your target culture. I’ve discovered wonderful authors that are often unknown to English speakers. Famous authors translated into English are even more wonderful in their own language. iTalki teachers, friends and Google are great ways to find recommendations for these.

7. Writing

When we listen and read it can be easy to fool ourselves in to believing we know how a language works. When we speak we usually make and get away with a litany of errors, even in our native language. Writing is a very different story.

When we write, it forces our language knowledge out into the open. It checks mercilessly that we’ve internalised its grammar rules and exceptions. This makes writing the most challenging of the seven components of language.

As a result, it can be tempting to ‘forget’ to make time for writing and focus on the other six aspects. Don’t do it. Practicing writing is hard but there is no better way to take your language skills to the next level.

Here’s a simple four step process to help get started with self-directed writing:

  • Write little and often – try five minutes of writing twice a day. This is better than putting 10 minutes of writing off for a week.
  • Start on paper – this forces us to check our spelling and grammar without the help of modern technology. Try to write from your head and not to get sidetracked looking things up.
  • Digitise and correct your writing – show your writing to a friend or upload it to the free correction services at iTalki or Lang-8. Store any spelling or grammar errors in your SRS.
  • Re-write the corrected text on paper again. This perfect version locks corrections down in your head.

Often one of the biggest barriers to writing can be not knowing what to write about. You don’t need to compose War and Peace. Instead, why not write:

  • About your day – either a journal of what you did or your reflections on what went on. Worried that your day sounds boring? Make something up!
  • A summary or opinion of a film, book or article that you’ve seen or read recently
  • A response to someone else’s questions or writing

Writing doesn’t always have to be public. That said, language is all about communication so why not try writing in some of the following places:

  • Language Learning Communities. iTalki and Lang-8 are great examples of communities organised around language learning.
  • Messaging apps. Tandem is an amazing app that’s built for language learning. Otherwise, get tapping on WhatsApp, WeiXin, iMessage or even your favourite dating app.
  • Blogs and Forums. These are great place to write about any interests you have, from sports to travelling. Why not post some reviews on TripAdvisor?
  • Social Media. Even FaceBook and Instagram can become good places to practice your new language.
  • Email. Some of my best and most rewarding (reading and) writing takes place in emails with friends from around the world.

Writing in a foreign language can feel daunting. Writing online even more so. But remember, it’s not only OK to make mistakes – it’s a critical part of the language learning process.

Advanced TipsContents

Becoming a local

There is more to being mistaken for a local than speaking the language with perfect pronunciation. Body language, dress and other non-verbal queues are also important.

When you have the opportunity to visit a country take a few minutes to look at the people around you:

  • What clothes do they wear?
  • What facial expressions do they have as they speak?
  • What distance do they stand from other speakers?
  • What are they doing with their hands?
  • How do they handle personal grooming and hairstyles?
  • What postures do they assume when standing or sitting?
  • How much eye contact do they make?
  • What other unique features make them different from me?

Once you’ve taken a few notes, make a game of trying to emulate the local crowd! Few moments are more satisfying than being mistaken by a local for one of their own.

Exam Preparation

Passing an exam is (by itself) a terrible reason to learn a language. Yet, as part of a broader strategy, they can be very useful. First, booking an exam is a great SMART goal. It gives you a concrete milestone to aim for and puts a bit of fear in your belly. Second, it can force you out of your comfort zone and patch up any holes in your knowledge.

Nailing exams is 50% what you know (see Learning how to Learn), 40% familiarity with the paper and 10% luck. Familiarity with the paper is the most overlooked of these three.

Here are a few tips to make sure you know what’s coming and how to show your best self on the day:

  • Buy exam preparation guides. Inside you’ll find break downs of the papers, perfect answers as well as tips and common pitfalls. They also often come with 3 – 4 practice papers and an answer book. There are usually one or two popular/official providers. These things are worth their weight in gold. Ask your teacher, Google or the exam board for advice here.
  • Find exam specific vocabulary lists. Sometimes exam boards are explicit about exactly what vocabulary you must know. Otherwise make sure to note and add any new vocabulary from exam guides and past papers to your SRS.
  • Do at least 4 – 8 practice papers. The more the better. As well as the preparation guides look on the examiner’s official website for past papers. Start these at least a month in advance and increase the intensity as you approach the exam day. Your teacher and Google can help you find these.
  • Do half your practice papers under exam conditions. This will tell you where you have a tendency to get stuck and need more work. It will also reduce stress on the day by upfronting it earlier in the process.
  • Get advice from other language learners. Ask a few people who have already taken the paper for tips and tricks. How did they prepare? What surprised them on the day? The iTalki community is a great place for this.
  • Get a good night of sleep. A good night of rest is always worth more than squeezing in one last minute practice paper.

Usually the exam will test you on each of the four practical skills discussed above. Here are some tips on preparing for each:

  • Speaking. Schedule practice oral exams with your (iTalki) teacher. Record yourself. Ask for feedback. This will feel stressful but you’ll be grateful for it later.
  • Listening. If you can’t find recordings, ask your (iTalki) teacher to record the transcripts for you.
  • Reading. Usually the easiest to practice – lots of past papers and noting of any missing vocabulary will do the trick.
  • Writing: Best practiced under exam conditions (time bound, no looking up). Write by hand if that’s what you’ll need to do on the day. Once done, follow the process outlined in the writing section to learn from your mistakes.

And remember, unless you’re at school, there are no consequences for passing or failing. Instead, exams are a great way to get valuable, external feedback on any gaps in your knowledge. You will learn much more from average marks on difficult exams than a perfect mark on an exam that’s far too easy.

Further ReadingContents

I’ve read many, many books on language learning. These are the only three that I recommend to friends taking on a new language. If you read them you’ll recognise many of these author’s tips repurposed in this article:

“Fluent in Three Months”, Benny Lewis: This is a great motivational book for those who think they aren’t “language people”. That said, don’t be misled by the title. Becoming fluent in three months requires almost total immersion and a generous definition of fluency. You’re also likely to forget everything within the next three months if your efforts stop there. There are no shortcuts to language learning, just ways to avoid long detours. Benny’s travel and language blog is also worth a visit.

“Fluent Forever: How to Learn Any Language Fast and Never Forget It” – Gabriel Wyner: A superbly practical book by this professional Opera Singer and polyglot. Particular emphasis on pronunciation and getting started with using SRSs for language learning. Gabriel’s website is also a treasure trove of language learning resources and tools

“Speak Like A Native: Professional Secrets for Mastering Foreign Languages”, Michael Janich: This much less well known book by an ex U.S., security agent is a worth addition to any language learner’s shelf. Full of practical tips and insights from the language programs at the CIA, NSA and State Department.


i. Myth 1: English is EnoughContents

The fact is that many native English speakers feel they have neither time nor motive to take on a new language.

“English is the global language”, some reason, “I don’t need anything else”. And from a purely utilitarian point of view they have a point. You can get by almost anywhere in the world with English. Google Translate can fill in most of the gaps.

But if we’re going to get all utilitarian then let’s at least be consistent. On a scale of one to ten how useful could learning a new language be to us in our lives and careers? How does this compare to binge watching Netflix or spending three hours a day on social media?


“Listen, going to the gym and learning a language are hard and painful things. Those other things make me happy, it’s a free world.”, others might argue.

And that’s fair enough, we all have limited time and energy. Nobody else has a right to say what makes us happy and how we should spend out time.

But let me at least try and convince you that learning a language is at least worth some consideration here.

A quick Google search will throw up many compelling and well referenced reasons – from health to wealth and wisdom.

For me: languages are a gate keeper to new friends, new authors, new places and new experiences. They transform the way I see, understand, travel and interact with the world. They improve my ability to focus and help my brain stay fit. These things all make me very happy and are more than worth the effort of an hour a day of patient labour.

At the end of the day, nobody can of should tell you how you to spend your time. But please do give languages another chance and you might be surprised where they take you.

ii. Myth 2: 'The Language Person'Contents

Like the Yeti, the fabled “Language Person” might, in fact, exist. But I know a lot of polyglots and yet I’ve never met one. Instead, learning a language takes a huge amount of hard work and time no matter who you are.

Despite this fact, the “Language Person” myth is a strong one. There are three main factors that contribute its persistence:

  • People lie (sometimes by omission). Or they forget. Wether intentional or by mistake, it feels good to be mistaken for a genius. Everyone who is good at something was once bad at it.
  • People only need to be a little better at a language than you for it to feel like a lot. This makes it very easy for someone who speaks a little of 12 languages to impress someone who speaks none of any of them.
  • It does get easier to learn languages the more you know. This happens for a number of reasons but it doesn’t change the fact that it still took a lot of work or that anyone else can do it. A “Language Person” isn’t born, they are made.

Please trust me on this one, anyone can learn a language. If you need more proof then consider the fact that almost every single person on the planet has managed to learn at least one.

If you’re trying and finding it difficult then guess what: it should be! Learning isn’t easy, that’s one of the things that makes it so rewarding. But if you follow some of the steps in this guide it shouldn’t be harder than necessary. Keep worrying away at it and progress is inevitable.

iii. Myth 3: I'm Too Old to Learn a LanguageContents

A common misconception is that once you’re an adult it becomes impossible to learn a new language.

Children do have a few advantages when it comes to language learning. These include:

  • Empty brains. It’s easier to fit a skyscraper in an empty field than a bustling metropolis.
  • Lots of time. If you could spend twelve hours a day playing and learning in a foreign language you’d fast become fluent in it too.
  • Patient teaching. There are few teachers more patient and persistent than parents.
  • A profound need. Survival in today’s world depends on learning at least one language.
  • A sense of fun. When was the last time you made up silly rhymes and songs to practice a new word you’ve learned? Learning is easy when it’s fun.

That said, as adults we enjoy two advantages that we shouldn’t underestimate:

  • Conceptual knowledge. We already understand the world around us. When we learn the word “car” we don’t also have to learn what a car is and does.
  • Self directed access. To better teaching. To better learning tools. To travel. To foreign friends. To reading. To writing. To clearer motives.

As adults we have fuller brains and much less free time. The fact is though that we also have a lot less to learn and are able to put our limited time to much better use.

Looking past the limitations of age lets us see and make the most of its advantages. It’s never too late to learn a language.

iv. What is Fluency?Contents

Fluency is like good driving – it starts when you no longer cause people around you to slow down or change direction.

The problem with all definitions of fluency (including mine) is that they’re very context dependant. You might be fluent in the first five minutes of conversation or at a restaurant. This in unlikely to qualify you as fluent enough to study a degree in a foreign language. (N.B., the faster a program claims to teach a language the more limited this definition usually is.)

This is where frameworks like the Common European Framework of Reference for Languages (CEFR) come in. Other frameworks do exist and it’s possible to convert between them. In the interests of keeping things simple, you’ll find the CEFR definitions below.

A good, conservative definition of “fluency” is one beginning at B2.

The Common European Framework of Reference for Languages (CEFR)

A1 Basic User – Breakthrough or beginner

  • Can understand and use familiar everyday expressions and very basic phrases aimed at the satisfaction of needs of a concrete type.
  • Can introduce him/herself and others and can ask and answer questions about personal details such as where he/she lives, people he/she knows and things he/she has.
  • Can interact in a simple way provided the other person talks slowly and clearly and is prepared to help.

A2 Basic User – Way stage or elementary

  • Can understand sentences and frequently used expressions related to areas of most immediate relevance (e.g. very basic personal and family information, shopping, local geography, employment).
  • Can communicate in simple and routine tasks requiring a simple and direct exchange of information on familiar and routine matters.
  • Can describe in simple terms aspects of his/her background, immediate environment and matters in areas of immediate need.

B1 Independent User – Threshold or intermediate

  • Can understand the main points of clear standard input on familiar matters regularly encountered in work, school, leisure, etc.
  • Can deal with most situations likely to arise while traveling in an area where the language is spoken.
  • Can produce simple connected text on topics that are familiar or of personal interest.
  • Can describe experiences and events, dreams, hopes and ambitions and briefly give reasons and explanations for opinions and plans.

B2 Independent User – Vantage or upper intermediate

  • Can understand the main ideas of complex text on both concrete and abstract topics, including technical discussions in his/her field of specialisation.
  • Can interact with a degree of fluency and spontaneity that makes regular interaction with native speakers quite possible without strain for either party.
  • Can produce clear, detailed text on a wide range of subjects and explain a viewpoint on a topical issue giving the advantages and disadvantages of various options.

C1 Proficient User – Effective Operational Proficiency or advanced

  • Can understand a wide range of demanding, longer texts, and recognize implicit meaning.
  • Can express ideas fluently and spontaneously without much obvious searching for expressions.
  • Can use language flexibly and effectively for social, academic and professional purposes.
  • Can produce clear, well-structured, detailed text on complex subjects, showing controlled use of organizational patterns, connectors and cohesive devices.

C2 Proficient User – Mastery or Proficiency

  • Can understand with ease virtually everything heard or read.
  • Can summarize information from different spoken and written sources, reconstructing arguments and accounts in a coherent presentation.
  • Can express him/herself spontaneously, very fluently and precisely, differentiating finer shades of meaning even in the most complex situations.

v. How Long Will it Take?Contents

It takes ~200 hours of good, guided study to go up one level on the CEFR framework. That’s an hour a day for just over two years to reach B2 (the starting point for fluency) for an easy language.

Here are some factors that will influence this estimate:

  • Language difficulty. More difficult languages (like Japanese) can take up to four times longer for English speakers to learn than simpler ones (like Spanish).
  • Previous experience. From phoneme and vocabulary overlaps to understanding the language of grammar – the more languages you know the easier they are to learn.
  • Quality of study. Practice must be purposeful. Guided study that keeps pushing you will achieve more than staying in your comfort zone.
  • Intensity of study. Forgetting is natural and inevitable. Taking 6 month gaps between study periods will increase the total number of hours you need.
  • Age does make a difference neural plasticity but it’s less important than we often think.

Everyone has an opinion but the one thing that all reliable estimates have in common is this: it takes a very long time to learn a language. This shouldn’t be a surprise. It also takes a very long time to learn to draw or even passably play a musical instrument or new sport.

It’s important to understand what you’re getting in to when you commit to learning a new language. It’s also why motivation is such an important part of the learning process.

vi. Languages: by FrequencyContents

For a table breaking down the top languages in the world by native and non-native speakers see this article on Wikipedia.

vii. Languages: by DifficultyContents

This table lists many languages by their difficulty to learn for English speakers. It’s said to come from the U.S. Foreign Services Institute (FSI). Though reposted widely online I’ve not yet found a link to the original. In any case, it makes a lot of sense.

The time required to learn a language roughly doubles between categories. In other words a category III language takes four times longer to learn than a category I language. The CEFR definitions and ~200h per level estimate are a good starting point for category I.

* Languages with asterisks are more difficult to learn than those in the same category.

Category I
Languages closely related to English

  • Afrikaans
  • Danish
  • Dutch
  • French
  • * German
  • Italian
  • Norwegian
  • Portuguese
  • Romanian
  • Spanish
  • Swedish

Category II
Languages with significant linguistic and/or cultural differences from English

  • Albanian
  • Amharic
  • Armenian
  • Azerbaijani
  • Bengali
  • Bosnian
  • Bulgarian
  • Burmese
  • Croatian
  • Czech
  • * Estonian
  • * Finnish
  • * Georgian
  • Greek
  • Hebrew
  • Hindi
  • * Hungarian
  • Icelandic
  • Khmer
  • Lao
  • Latvian
  • Lithuanian
  • Macedonian
  • * Mongolian
  • Nepali
  • Pashto
  • Persian (Dari, Farsi, Tajik)
  • Polish
  • Russian
  • Serbian
  • Sinhalese
  • Slovak
  • Slovenian
  • Tagalog
  • * Thai
  • Turkish
  • Ukrainian
  • Urdu
  • Uzbek
  • * Vietnamese
  • Xhosa
  • Zulu

Category III
Languages which are exceptionally difficult for native English speakers

  • Arabic
  • Cantonese
  • Mandarin
  • * Japanese
  • Korean

Book Crunch: “Deep Work”, Cal Newport

Deep Work, Cal Newport

Deep Work, Cal Newport

“Deep Work: Rules for Focussed Success in a Distracted World”, Cal Newport
Print length: 305 pages. Buy on Amazon.

Perfect for you if:

  • You work more than 8 hours per day and/or on the weekends.
  • You sometimes feel like you’re drowning in a sea of admin.
  • You can’t remember the last time you managed to “get some real work done”.

This excellent book by MIT alumni and Georgetown professor Cal Newport is a must read for anyone wanting to focus on the things that really matter by cutting down on fire-fighting, meeting attendance, email herding, and the pernicious effects of internet browsing and social media.

The book begins by categorising work as either deep or shallow where:

  • Deep work is made up of professional activities performed in a state of distraction-free concentration that push your cognitive abilities to their limit. These efforts create new value, improve your skill and are hard to replicate (similar in concept to purposeful practice); and
  • Shallow work is made up of non cognitively demanding, logistical style tasks often performed while distracted. These efforts tend to not create much new value in the world and are easy to replicate.

The first half of Cal’s book explains why deep work is so valuable, rare and meaningful in today’s fractured, winner-takes-all world. He convincingly argues that our attention is often so fractured that we actually accomplish very little genuinely deep work in a typical day.

Perhaps more worrying is his claim that months and years of exposure to shallow work and distraction has a long-lasting negative affect on our ability to focus our attention that is not quickly or easily reversed.

The broad and substantial evidence base in this section draws deeply from examples set by influential thinkers and doers throughout history (from Carl Jung and Nate Silver to Bill Gates). Though it doesn’t lend itself well to being crunched it is well worth reading if any further motivation for action is needed beyond our own personal experiences of the reward and meaning to be found in the too rare moments of stillness that allow us to “get some real work done”.

The second half of Cal’s book is full of powerful and actionable suggestions to shift our balance back towards deep work. These practical tips include ways to identify and eliminate existing bad habits, build new good habits, implement structural quick-wins and actively train and improve our attention. I have personally experimented with most of Cal’s suggestions (with some minor modifications from other authors) and cannot recommend the effort to follow through with them strongly enough.

Fighting for more deep work in our lives means doing more of the things that are important to us and less of the things which aren’t. At it’s core, Cal’s book reminds us that our days can and should be focused not just on “getting things done” but on “getting valuable things done”.

In other words, both efficiency and effectiveness are requirements for meaningful and purposeful action that leads to a productive life, filled with energy and balance.

What follows are my brief notes on Cal’s main points and suggestions.

Drowning in the Shallows

The breadth of and our access to network tools (physical: open plan offices, meetings / digital: email, instant messaging, social media etc…) has greatly increased, but our ability to pick selectively among and effectively use them has not.

Instead we tend to adopt tools that offer any benefit at all without carefully weighing those benefits against their disadvantages and opportunity costs – i.e., the time we could be spending on activities that are more valuable (we basically end up on the wrong side of Pareto’s 80/20 principle).

Additionally, we are surrounded by distractions which are in fierce, active competition for and have become very effective at capturing our attention (advertising, messaging, social media, mobile apps, television, internet etc…). Willpower is a finite resource (see Ego depletion) and the reward of giving in to these distractions creates powerful habits of instant gratification.

A bias for instant gratification is dangerous because shallow work is so much cognitively easier than deep work. Attending meetings, becoming a human email router and ticking off shallow to dos all provide momentary satisfaction and an illusion of business but this comes at the expense of deep thought, value creation and a wider sense of meaning in our work.

Meanwhile, we have shifted culturally into the habit of making work the centre of our lives. We have come to view our free-time as simply the sub- and post-script to our days/weeks and so we spend more and more time working. There is, however, no evidence for an equivalent gain in productivity (see Parkinson’s law).

In fact, 37Signals is an example of one company that has successfully experimented with reducing the work week to four days and cutting out June without any meaningful reduction in value creation.

Into the deep

Three to four hours of continuous, undisturbed deep work each day is all that it takes to see a transformational change in our productivity and our lives.

To those hoping to put some of these habits into practice I would suggest focussing on one initiative at a time and having patience. You wouldn’t try and run a marathon on your first run, likewise, building a commitment to increasingly productive deep work means working on our brain’s dad bod. It is a slow process of habit forming and increasing mental fitness.

All personal change demands time, effort, persistence and discipline as well as the temporary discomfort of changing not only our own mindsets but also the expectations and mindsets of those around us.

1. Learn to categorise tools and tasks as deep or shallow:

Cal devotes several pages to some good, practical examples that work through through the following process:

  1. Identify a desired big-picture outcome in a particular area of life (family, friends, health, wealth, work etc…)
  2. Identify just two or three activities that contribute the most towards this outcome (see Pareto’s 80/20 principle)
  3. For each tool or task that currently consumes time and energy in this area of life, ask ourselves: “Is this tool or task integral to the activities that help me make progress towards my desired outcomes?”
  4. If the answer is no then quit the tool or task

Though our goals and circumstances are personal, the majority of us will find that many of the tools and activities that we give our time and energy to fail to pass this simple test.

For example, is it better to spend two hours catching up on the life developments of all our FaceBook friends or to go out with one or two close friends for dinner? Unless our career or personal circumstances depend on maintaining a broad network through frequent, light communication the answer is clear.

Giving up tools and tasks entirely might seem extreme but remember; willpower is finite and the danger inherent in these distractions extends beyond the time that we use them to the focus-destroying habits we form through them.

For a quick quantitative guideline on how deep a piece of work is, ask: “How many months would it take to train a smart graduate student with no experience in my domain to do this task?”. This rule of thumb can help to keep us honest about whether to prioritise work on accounting presentations or attending process and update meetings vs. high impact ‘only-me’ activities.

2. Make quick structural changes that encourage deep work

Breaking and forming habits becomes much easier when we make quick, external structural changes that eliminate or introduce the cues that trigger them. These changes help make new habits the course of least resistance and most importantly they eliminate the roll of willpower in falling back into old ones.

Here are the structural changes Cal suggests we make to simplify our lives and help us work more deeply:

  1. Disable all incoming call/message notifications and badges
    In the last 10 years, including three years as an analyst at McKinsey, I’ve never missed a single professional or personal call or message that couldn’t wait.
  2. Become hard to reach
    Set sender filters, filter emails with rules and use auto-responders to manage reply expectations. Ask people to respect your time and energy and they will.
  3. Quit social media
    Experiment first with a secret, total 30 day social media fast if that helps. Like Cal I haven’t used social media in 8 years and my life has been much richer for it. 
  4. Work in a quiet place
    Open-plan offices are the bane of deep work; a private room or library is best, noise cancelling headphones and music without words will do in a pinch.
  5. Work at a quiet time
    Ask the most effective people you know when they wake up. It will be early, when there’s nobody else up to disturb them.
  6. Limit internet access during deep work time
    • Gather everything needed before beginning a session of deep work
    • Alternate on and offline work time (see Pomodoro technique)
    • Block problem websites during working hours (check out Freedom)

3. Get visibility on deep vs. shallow time by minuting the day:

The first step to changing anything is to measure it.

Start keeping an honest record (on paper / in your calendar) of how time is actually being spent during each day.

Review this record at the end of the day to get a sense of how much time is really being spent on deep vs. shallow work.

4. Determine a fixed end point to the work day and stick to it

  1. Reframe our day towards our free-time instead of our work.
    Even if we enjoy our work we shouldn’t forget that financial gain is only a means to an end, not an end in itself.
    If you could retire tomorrow what would you do with your free-time? Start seeing the time outside of work as if you were already retired.
  2. Commit to a fixed end time to your day
    Make commitments to our children, book a yoga class, make plans with a friend, order a food delivery to our home etc…
    Set a quitting time at the end of the day and do whatever it takes to make ourselves stick to it.
  3. Plan backwards
    Once we have a quitting time we can start fighting Parkinson’s law (the tendency for work to expand to fill the time available to it)
    Identify the things which have to get done to day and plan backwards
  4. Say no to shallow work and off-task commitments
    Run every incoming request through the process outlined at the start of these initiatives
    Protect the end time by ruthlessly declining and then eliminating shallow work

5. Train our attention

As well as taking steps to eliminate shallow work from and introduce the conditions for deep work into our lives Cal also suggests a number of exercises to actively help strengthen our ability to effectively direct our attention.

Much like meditation, each of these exercises involves choosing a single object of focus, noticing when attention has wandered and then gently bringing attention back to the initial object. Beyond strong and consistent anecdotal evidence, such practices have a proven physical impact on the attention centres of the brain:

  1. Become friends with boredom
    When standing in line or waiting for a friend, resist the temptation to instantly distract the mind with needless activity. Instead practice just being in the present moment.
  2. Practice thinking whilst walking
    Get into the habit of practicing thinking on a single, well defined problem or topic that is important to you whilst engaged in a physical activity that doesn’t require much mental exertion. This form of walking meditation not only improves attention but also has the added benefit of increasing productivity.
  3. Give the mind a work out with intense study or memorisation skills
    Spending time each day learning to to e.g., use our visual memory to memorise a pack of cards isn’t just a good trick to impress friends at the pub. This kind of mental gymnastics also forces us to flex our attention muscles with far reaching implications for the rest of our lives.

Related Reading

“Deep Thinking: What Mathematics Can Teach Us About the Mind”, William Byers: A great use of an experience we all remember (learning basic math) to show the importance of creativity in making cognitive learning leaps.

“The Art of Learning: An Inner Journey to Optimal Performance”, Josh Waitzkin: A superb first hand account showing the overlap of basic deep learning principles in two very different fields (chess and martial arts) from the protagonist of “Searching for Bobby Fisher”.

“Getting Things Done: The Art of Stress-Free Productivity”, David Allen: A cornerstone and very practical work on productivity from the world renowned David Allen – easily one of my top most life-changing reads, though it is aimed for at efficiency than effectiveness.

“A Mind for Numbers: How to Excel at Math and Science”, Barbara OakleyA fantastic book with more attention to applying deep work to learning (book crunch here)

“Daily Rituals: How Great Minds Make Time, Find Inspiration, and Get to Work”, Mason Currey: A wonderful book full of examples of the daily routines of some of history’s most famous scientists, authors, poets and artists. Perfect for dipping in and out of and giving great real life examples of how some of our best minds have used the principles explained in Cal’s book.

TANQ entries for “Deep Work”

TANQ is WhyWhatHow’s growing central library of thoughts, anecdotes, notes and quotes.

“Deep Work: Professional activities performed in a state of distraction-free concentration that push your cognitive abilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.”

Cal Newport Deep Work

“Shallow Work: Non-cognitively demanding, logistical style tasks, often performed while distracted. These efforts tend not to create much new value in the world and are easy to replicate”

Cal Newport Deep Work

“The Deep Work Hypothesis: The ability to perform deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable in our economy. As a consequence, the few who cultivate this skill, and then make it the core of their working life, will thrive.”

Cal Newport Deep Work

“Part of what fuelled social media’s rapid assent… is its ability to short-circuit this connection between the hard work of producing real value and the positive reward of having people pay attention to you.”

Cal Newport Deep Work

“For someone new to such [deep] practice … an hour a day is a reasonable limit. For those familiar with the rigours of such activities, the limit expands to something like four hours, but rarely more.”

Cal Newport Deep Work

“Treat shallow work with suspicion because its damage is often vastly underestimated and its importance vastly overestimated.”

Cal Newport Deep Work

“Schedule every minute of your day… When you’re done … every minute should be part of a block. You have, in effect, given every minute of your workday a job. Now, as you go through your day, use this schedule to guide you.”

Cal Newport Deep Work

“A deep work habit requires you to treat your time with respect.”

Cal Newport Deep Work

“A tactic that works well for me [when declining low-value requests] is to be clear in my refusal but ambiguous in my explanation for the refusal.”

Cal Newport Deep Work

“Fixed schedule productivity is a meta-habit that’s simple to adopt but broad in its impact. If you have to choose just one behaviour that reorients your focus toward the deep, this one should be high on your list of opportunities.”

Cal Newport Deep Work

“A commitment to deep work is not a moral stance and it’s not a philosophical statement – it is instead a pragmatic recognition that the ability to concentrate is a skill that gets valuable things done.”

Cal Newport Deep Work

“There’s also an uneasiness that surrounds any effort to produce the best things you’re capable of producing, as this forces you to confront the possibility that your best is not (yet) that good.”

Cal Newport Deep Work

“Three to four hours a day, five days a week of uninterrupted and carefully directed concentration, it turns out, can produce a lot of valuable output.”

Cal Newport Deep Work

“To build your working life around the experience of flow produced by deep work is a proven path to deep satisfaction.”

Cal Newport Deep Work

[ To understand where a task fits on the shallow-to-deep scale ask a simple question: ] “How long would it take (in months) to train a smart, recent college graduate with no specialised training in my field to complete this task?”

Cal Newport Deep Work

Book Crunch: “Man’s Search for Meaning”, Viktor Frankl

Man's Search for Meaning, Viktor Frankl

Man's Search for Meaning, Viktor Frankl

“Man’s Search for Meaning”, Viktor Frankl
Print length: 161 pages. Buy on Amazon.

Perfect for you if:

  • You’re curious about why we exist or what it all means
  • You sometimes / often struggle with apathy or boredom
  • Despite recently accomplishing a major goal you still feel empty inside

This short, moving and life-changing book was written by Jewish-Austrian neurologist / psychiatrist and holocaust survivor Victor Frankl.

The book’s brutal and honest first hand accounts of life and loss in a concentration camp (worth reading in and of itself) are a vehicle for Frankl’s wider theories and deep insights into man’s search for meaning. These theories were his life work (even before his transportation to Auschwitz) and are at the core of Logotherapy (logos = meaning), a major school of modern psychotherapy.

The Meaning of Life

“He who has a why to live for can bear almost any how.”, Friedrich Nietzsche

The essence of Frankl’s theory is as simple as it is universal and runs as follows:

Man’s primary motivational force is the striving for meaning in one’s life.

A frustrated will to meaning leads to an existential vacuum that is the mass neurosis of the present time.

This existential vacuum can be described as a private and personal form of nihilism and manifests itself primarily in states of boredom and anxiety.

But there is no objective or general meaning to life. We cannot strive for meaning as we cannot strive for success or happiness.

Instead, meaning (Why) ensues primarily from active purpose (a What) which can be a thing (a work or deed) or a person (love or responsibility).

However, life also questions us constantly with a passive stream of Whats (including unavoidable suffering) to which we must respond and from which meaning can also ensue.

In this case, a strong individualistic sense of self, of Who we are, becomes the Why for how we respond to those Whats.

No matter what external limitations we face, we are always free to choose Who we are and how we respond.

This allows us to tap into an unassailable source of inner freedom and personal value.

A Story About Fate

A short story from the book about fate that enjoyed I so much I thought it worth preserving/sharing:

A rich and mighty Persian once walked in his garden with one of his servants. The servant cried that he had just encountered Death, who had threatened him.

He begged his master to give him his fastest horse so that he could make haste and flee to Teheran, which he could reach that same evening. The master consented and the servant galloped off on the horse.

On returning to his house the master himself met Death, and questioned him, “Why did you terrify and threaten my servant?” “I did not threaten him; I only showed surprise in still finding him here when I planned to meet him tonight in Teheran,” said Death.

Related Reading

“To Have or To Be”, Erich Fromm

“The Art of Loving”, Erich Fromm

“Siddhartha”, Herman Hesse

“The Subtle Art of Not Giving a F*ck”, Mark Manson

TANQ entries for “Man’s Search for Meaning”

TANQ is WhyWhatHow’s growing central library of thoughts, anecdotes, notes and quotes.

The existential vacuum manifests itself mainly in a state of boredom.

Victor Frankl Man’s Search for Meaning

Don’t aim at success – the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue and it only does so as the unintended side effect of one’s dedication to a cause greater than oneself or as the by product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it.

Viktor Frankl Man’s Search for Meaning

Delusion of Reprieve: “The condemned man, immediately before his execution, gets the illusion that he might be reprieved at the very last minute.

Viktor Frankl Man’s Search for Meaning

Delusion of Reprieve: “The condemned man, immediately before his execution, gets the illusion that he might be reprieved at the very last minute.

Viktor Frankl Man’s Search for Meaning

An abnormal reaction to an abnormal situation is normal behaviour

Viktor Frankl Man’s Search for Meaning

The most painful part of beatings is the insult which they imply.

Viktor Frankl Man’s Search for Meaning

No man should judge unless he asks himself in absolute honest whether in a similar situation he might not have done the same thing.

Viktor Frankl Man’s Search for Meaning

A rich and mighty Persian once walked in his garden with one of his servants. The servant cried that he had just encountered Death, who had threatened him. He begged his master to give him his fastest horse so that he could make haste and flee to Teheran, which he could reach that same evening. The master consented and the servant galloped off on the horse. On returning to his house the master himself met Death, and questioned him, “Why did you terrify and threaten my servant?” “I did not threaten him; I only showed surprise in still finding him here when I planned to meet him tonight in Teheran,” said Death.

Viktor Frankl Man’s Search for Meaning

Everything can be taken from a man but one thing: the last of the human freedoms – to choose one’s attitude in any given set of circumstances, to choose one’s own way … It is this spiritual freedom – which cannot be taken away – that makes life meaningful and purposeful.

Viktor Frankl Man’s Search for Meaning

We needed to stop asking about the meaning of life and instead to think of ourselves as those who ere being questioned by life.

Viktor Frankl Man’s Search for Meaning

Progressive automation will probably lead to an enormous increase in the leisure hours available to the average worker. The pity of it is that many of these will not know what to do with all their newly acquired free time.

Viktor Frankl Man’s Search for Meaning

The Meaning of life differs from man to man, from day to day and from hour to hour … what matters, therefore is not the meaning of life in general but rather the specific meaning of a person’s life at a given moment.

Viktor Frankl Man’s Search for Meaning

Live as if you were living already for the second time and as if you had acted the first time as wrongly as you are about to act now!

Viktor Frankl Man’s Search for Meaning

We can discover the meaning of life in three different ways: (1) by creating a work or doing a deed; (2) by experiencing something or encountering someone; and (3) by the attitude we take toward unavoidable suffering.

Viktor Frankl Man’s Search for Meaning

To suffer unnecessarily is masochistic rather than heroic.

Viktor Frankl Man’s Search for Meaning

The pessimist resembles a man who observes with fear and sadness that his wall calendar, from which he daily tears a sheet, grows thinner with each passing day. On the other hand, the person who attacks the problems of life actively is like a man who removes each successive leaf from his calendar and files it neatly and carefully away with its predecessors, after first having jotted down a few diary notes on the back.

Viktor Frankl Man’s Search for Meaning

Hyper Intention: “A forced intention makes impossible why now forcibly wishes.”

Viktor Frankl Man’s Search for Meaning

“Humor was another of the soul’s weapons in the fight for self-preservation. It is well known that humor, more than anything else in the human make-up, can afford an aloofness and an ability to rise above any situation, even if only for a few seconds.”

Viktor Frankl Man’s Search for Meaning

Why it’s not you, it’s me.

It's not you, it's me

It's not you, it's me

Perfect for you if:

  • You just started a new friendship or relationship
  • You feel let down by or angry at yourself or someone else
  • There are people in your life that you just can’t seem to forgive


When we feel frustrated or let down by someone else (or even ourselves) it can be helpful to remember that that person has, in fact, always been that person – what has really failed here are the expectations that we have set for them.

Climate is made up of complex seasons, weather systems and local weather patterns. Even with these general rules it can be highly unpredictable. We wouldn’t make sweeping generalisations about the general global climate from a single Summer’s day. We definitely wouldn’t stubbornly refuse to update those expectations in the face of changing context or time.

In the same way, people have personalities, phases, moods and emotions. Perhaps we judged them too hastily (halo effect). Perhaps we should have realised earlier that we needed to update our expectations (consistency bias) or chose to ignore the clues that those expectations were misplaced (confirmation bias). Perhaps the shortcuts (heuristics) that we used to set those expectations are unrealistic or hypocritical.

In any case, though learning something new about a person may be hard (especially if it undermines the foundations of some best laid hopes and plans), blaming someone else for our own misunderstandings or expending time and energy on anger, resentment or trying to change them against their will are about as effective as shaking our fists at a thunder storm.

On the other hand, taking responsibility for failures in our own judgement makes forgiveness easy. It helps us recognise the obstacle we’ve encountered as an opportunity for growth and to see each setback as a stepping stone to better laid expectations and relationships in the future.

At the end of the day, it takes thousands of new situations over many decades to start getting to know ourselves, let alone another person, and even then both can surprise us. So, when the real world and the world in our heads diverge, it can be helpful to reflect that the real problem here may simply be that we’ve mistaken the weather for the climate.

After all, being human is complicated and sometimes we all forget to pack a rain coat.

Creation is in the eye of the beholder

All it takes is a glimpse, a flash of laughter, perhaps even a single sentence and, just like that, we’ve built a deep and complex impression of a total stranger’s character. It is one of the most amazing abilities of our already remarkable brain.

Think about it, within moments of seeing or hearing about someone we subconsciously use shortcuts (heuristics) to bring our entire knowledge of the world together, fill the gaps between a handful of data points and create a unique and totally imaginary human being in our heads.

This imaginary model allows us to make useful assumptions about who a stranger is and our expectations of their (re)actions towards us and the world around them.

It’s these assumptions that enable us to cooperate quickly and effectively with strangers. It’s these expectations that are at the foundation of our ability to work in the extended social networks that have created humanity as we know it today.

But there’s no such thing as a free dinner and the super-fast and largely good-enough nature of our amazing shortcuts come at a cost.

The price of shortcuts

There are several major problems with the imaginary person that now lives in our heads:

  1. We base our impression on only a few data points.
  2. We fill the bits in-between with mostly made up information.
  3. We will go to extraordinary lengths to hold on to this initial model.

First impressions are a good example of giving too much emphases to a small number of data points. They’re also a good example of “the Halo effect” – our tendency to assume a lot about someone’s character or an object’s properties from only a handful of measures.

We know and fear the power and injustice of a bad first impression (though we are less likely to jump up and down about undeservedly good ones). They take away as unfairly from society’s minorities and misfits as they reward tall CEOs, good looking salesmen and attractive musicians.

But even beyond our more obvious biases we tend to fill the space between these data points with nonsense.

Sometimes we base our expectations on our understanding of how we are (or think we are) – this is what makes thieves so security conscious and murderers so paranoid.

More often we base those expectations on how believe people should be – including standards we frequently fail to live up to ourselves.

And occasionally we even build people up to be who we want or need them to be – from fools and devils to white knights or damsels in distress.

Once formed, the character of this imaginary human being becomes frustratingly persistent. We go to great lengths to preserve continuity and consistency in our lives. It is easier to pay more attention to information that agrees with our existing beliefs (confirmation bias) than it is to openly challenge, break down and reconstruct them.

As a result, it is unsurprising that people often surprise us, both positively and negatively. And even less surprising that even then, it takes a huge number of examples across a wide variety of contexts to shift our first impressions.

But, over time, as we get to know the person in question, we add more and more data points to the model in our heads. The more data points we collect the more infrequent the surprises. The more infrequent the surprises the greater our self-confidence in predicting their behaviour.

Until eventually the model in our heade becomes so good that we begin to think of it as the same thing as the real person standing in front of us. We feel that we ‘know’ that person.

And then, disaster strikes.

The cost of over-confidence

At the height of our confidence, or in the face of our general beliefs about how people ‘should’ act, the person that we thought we knew acts in a way that is negatively inconsistent with our expectations. A part of the model seems to collapse, along with any plans we’ve laid on top of it, and it feels like something that was once very solid has been taken away from us.

And guess what, we don’t like things having taken away from us. In fact, scientists have consistently shown that having something taken away from us triggers a stronger emotional response than simply having it not given to us in the first place. This cognitive bias (deprival super reaction syndrome) is the same one that makes rolling back benefits or rewards from us when we are accustomed to receiving them so traumatic, even if there’s no longer any basis for those rewards to be in place.

Perhaps a parent or a friend wasn’t there for us when we needed and expected them to be. Perhaps they stole from you, or treated you unfairly or betrayed your trust. The result can be an intense emotional response of sadness and betrayal towards the person we perceive to have let us down. A response that often evolves into anger or denial (learned helplessness) if it can’t be escaped.

I’ve been on both sides many times and I know how helpless and disorienting it can feel. You feel wronged and the person who has wronged you just can’t seem to see why or how. In the absence of a solution the blame and recrimination can lead to tit for tatting which can itself temporarily or permanently damage a relationship.

But there is a solution.

It’s not you. It’s me.

And the solution starts with admitting that it is not the other person that has wronged us. It is us who has wronged them.

Recall that what’s actually fallen short here is our own mental model of a person. A model that is (and always has been) totally imaginary. A model full of expectations which we have set. Expectations which were probably at best inaccurate and at worst hypocritical or unobtainable.

Perhaps this person has actively misled us. But even so, the decision to build our model based on the full weight of their words rather than to keep our expectations open to the evidence of their actions was also ours to make.

The truth is that that person has always been that person. We just didn’t realise it until now.

Time for a new strategy

So we’ve learned something new about a person.

The bad news is that a few major hopes and dreams that we’d built on top of our shattered expectations might be smouldering in a sad little heap in the corner.

The good news is that, with only ourselves to blame, forgiving the other person becomes very easy. And that’s going to free up a lot of time and energy in pointless tit for tatting, moping and recriminations to focus on the important stuff. Namely, rolling up our sleeves and working out what to do next.

1. Pause – the power of not making things worse

First step: do nothing at all. We all have a remarkable talent for misperceiving, misinterpreting and misunderstanding. If I had a pound/euro/dollar for every time I’d made things worse by (re)acting before taking the time to pause and think I could probably bank roll World Peace. Even Abraham Lincoln’s wife would famously hide his most scathing letters until he’d had a chance to calm down.

It is rare that taking a moment to pause, observe and investigate before acting doesn’t lead to better decisions. With a little patience, situations often turn out to be much less dramatic than they first appeared. Sometimes, they even solve themselves entirely.

Creating a gap between observation and emotional response is one of the fundamental skills that can be learned through meditation. And if there were only one reason to take up twenty minutes of meditation a day, this would be it.

In the meantime, making a deal with ourselves to sleep on an emotionally charged situation before (re)acting is one of the greatest (and most challenging) habits we can form.

2. Understand – good decisions need good information

My life and the life of those around me would be and have been a lot more pleasant if I were better at “assuming benign (kind) intent”. People everywhere are generally good and kind and they rarely do things to intentionally hurt others. It is easy to assume the opposite, and occasionally we’d be right, but doing so by default can lead to many misunderstandings that would be otherwise easy to avoid.

What we really want here is to minimise future surprises and our best bet to do so is to really understand what’s going on before we make any changes to our models.

What could have been going through the other person’s head? Have I ever been on the other side of a similar situation? Do I know someone else who has? A period of extreme stress in someone’s life can cause them to think, speak or act in a way so uniquely out of character that it deserves special treatment. Is this one of those scenarios?

Talk to the other person but avoid generalisations, they will only trigger defensiveness. What exactly did they do, when, how? How did that make me feel? Give them space to explain. Remember, unless you’ve decided to end this relationship what you both want out of this discussion is to learn and move forwards.

3. Process – update our model and expectations

After we’ve paused and reflected it’s time to update our models and expectations. Does this piece of information tell us something about this person’s actions under just a few specific sets of circumstance? Or does it tell us something more about their character in general?

This step sounds simple but one of the hardest things for us to do is to face the consequences of admitting that we are wrong. This is especially true if we’ve held the suspect belief for a long period of time and doubly so if the new information is going to require us do a lot of thinking or make some disruptive changes.

Too often we fall into the trap of refusing to update our models (remember the persistence of first impressions) and hoping that the real world will change to fit us instead of the other way around. If you’ve ever tried to telepathically switch off your alarm clock in the morning and found it frustratingly non-compliant you know what I’m talking about.

If you’ve paused and taken the time to understand what’s going on then be brave and let go of your old views. You will thank yourself in the long run.

4. Act – decide what to do next

Once we’ve adjusted our model there’s only one question left to ask:

Knowing what I now know about this person, if I met them again today would I still get back into this relationship?

This kind of zero-based-thinking helps us to escape the strong gravity of invested time and energy that draws us back over and over again into a toxic relationship. By looking at the relationship as if it were starting today we can let go of the past and focus fully on the future.

If our answer to this question is no then the the best thing to do is to take steps to start getting out of the relationship as quickly as possible.

But if the answer is yes then it’s time to roll up our sleeves and focus on the future.

Working on the future

People can and do change. Change starts with a thought. Thought leads to action. Action leads to habit. And habits are the building blocks of personality.

But lasting change means breaking down deeply worn patterns of thought and action and laying new ones down. It takes time, effort, discipline, internal motivation and a lot of persistence.

Option 1: Change the other person

Think of the difficulties you’ve had breaking bad or building new, simple, well intentioned habits like waking up earlier, getting to the gym or browsing less social media. How much effort, how much strong internal discipline and motivation did that take? How many times did you fall back into old traps?

Now imagine trying to force that onto someone else. Is it any wonder that trying to change someone against their will is a waste of time?

But if a person genuinely wants to change then the best we can do is make it as easy for them as possible. It starts with creating an environment that allows and supports that change. Build trust, communicate openly and without judgement. Reinforce every positive step with love and praise.

Reflecting on our own experiences reminds us how hard it can be to change even the simplest of things. Forming a new habit takes time (at least 30 days) and daily effort so patience and focus on just one thing at a time are critical.

But perhaps the single most important step of all is to lead by example.

To change others we first have to be willing to change ourselves.

Option 2: Change ourselves

For those who like to give themselves a hard time whenever they let themselves down, I’ve found it helpful to remember this: everything written above applies as much to our relationship with ourselves as it does to our relationships with other people.

It’s ok to get things wrong and every obstacle we encounter is an opportunity to learn more about the world and people around us. Every mistake, every failed encounter, friendship or relationship helps us learn how to make the next one better.

It would be impossible to summarise even a fraction of the timeless advice given in the countless books that have been written on changing ourselves. Here are just a few of the things that I’m working on right now that have helped me make sense of the past, build better models for the future and work towards seeing the world with “a grand mother’s eyes”:

Expect the unexpected

Shortcuts (heuristics) are a critical part of the way our brain works. We can’t simply wake up one day and decide to have no expectations whatsoever.

But we can remember that our mental models are just simplified shortcuts for us to make sense of the world around us and, as a result, they are guaranteed to get things wrong.

Reminding ourselves of this fact helps us to keep a light hearted and flexible, rather than hostile, attitude to the unexpected.

Get to know ourselves

Perhaps the most effective way to make our models of other people more realistic is to build them not from expectations of how people should (or could) be but from how people actually are. And a good first step to that end is to become a bit more honest with ourselves.

Getting to know ourselves takes time and experience that is hard to speed up or manufacture. Understanding and admitting the difference between who we would like to be (or be perceived to be) and who we are takes introspection, courage and clarity.

The best thing we learn as we get to know ourselves better is the depth and complexity of our flaws. Acknowledging these flaws and taking it easier on ourselves will almost automatically lead to cutting the people around us more slack.

Ask yourself if you’re setting expectations for others that you can’t even keep yourself. Make time for meditation and honest self reflection at the start and end of each day. Travel, find mentors, read and throw yourself into new and uncomfortable experiences as often as you can.

‘A fool thinks himself to be wise, but a wise man knows himself to be a fool’.

Finally, as Shakespeare reminds us, you can never have too much information on the fallibility of the brain and its cognitive biases.

Excessive self-regard, availability mis-weighing, confirmation bias, halo effect, deprival super reaction syndrome – these are just a handful of the ways in which our otherwise miraculous brain trips us up on a daily basis.

Learning about and accepting our flaws reminds us that if the world isn’t living up to expectations then the problem is more likely to be with our expectations than with the world.

How to Travel Plan Like a Long-term Travel Ninja

Travel Planning Dropbox Folder

Perfect for you if:

  • You’re travelling to learn and experience as much as possible.
  • You want to plan a big trip independently but have no idea where to start.
  • You often find yourself finding out all the great stuff you missed after you leave.

“In preparing for battle I have always found that plans are useless, but planning is indispensable.” Dwight D. Eisenhower

There’s an infinite number of ways to go about travel planning, or even not to go about it at all – and this post is not about trying to convince you either way.

Instead, it’s just an insight into my own system of travel planning that’s evolved from the last few years and ~70 countries of travel blunders as well as the kind and patient help and advice of hundreds of fellow travellers and travel buddies along the way. (N.b., I travel with pretty much exactly the same set up in my trusty 40 litre backpack no matter where I’m going so packing doesn’t feature here! More in another post.)

I won’t always follow every step exactly (or at all), and the effort I put into each plan really depends on the country I’m travelling to, the way I’m travelling and also how travelled or planned-out I’m feeling (in fact giving up on planning is a good indicator that it’s time for me to stop, settle down and recharge).

But so far I’ve found, aside from getting more out of my time and money in each country, that it’s only when I have a solid back up plan in my back pocket (as well as the knowledge in my head that it took to put it together) that I’m able to totally relax, tear it up and travel most spontaneously when opportunity comes knocking!

The top section that follows is just the raw checklist but click on the orange header links at the top of each section for more detail.

Region/Country Level Planning

1. Define success
☐ Write a why statement (bullets)
☐ Visualize success (bullets)

2. Identify barriers
☐ Visa requirements
☐ Festivals / holidays
☐ Health / safety risks
☐ Weather (seasonal, regional)

3. Download or gather links to travel information
☐ CIA World Fact Book
☐ Lonely Planet
☐ Wikipedia
☐ Wikitravel / Wikivoyage
☐ Top 10 lists (Google)
☐ Itineraries (Google)

4. Do background reading
☐ Lonely Planet (esp. back section)
☐ Wikipedia
☐ Wikitravel
☐ Other

5. Synthesise a “Top 10” list
☐ Friends / Travel Buddies
☐ Lonely Planet
☐ Wikitravel / Wikivoyage
☐ TripAdvisor
☐ “Top 10” lists (Google)

6. Plot “Top 10” list on Google MyMaps

7. Draft an itinerary
☐ Draft a rough itinerary
☐ Check vs. 3rd party itineraries
☐ Check vs. success statements

8. Firm up itinerary
☐ Research travel options/times between locations
☐ Check transport, ticket and accommodation availability
☐ Calendarise itinerary

9. Refine as you go
☐ Update the plan based on:
Location Level Planning; and
→ On the ground information
★ N.b., Don’t let the plan get in the way of the trip

10. Look back on the trip
☐ What did I do? What didn’t I do?
☐ What did I learn? What was surprising?
☐ What went well? What would I do differently?

Location Level Planning

1. Repeat steps 3 – 6 from country-level planning

2. Finalise and book accommodation and logistics
☐ Book accommodation
☐ Book inward / outward travel

3. Download local resources offline to iPhone
☐ Google maps
☐ Ulman maps
☐ TripAdvisor

3. Check travel and accommodation calendar entry notes complete

Sight/Activity Level Research

For each major sight/activity repeat steps 3 – 4 of country planning

1. Define success

Write a Why Statement:

Why: Really helps me prioritise effectively between options before and during the trip by surfacing my real motives for visiting a country.

What: Anything from a few bullet points to a wordy treatise, whatever I need to get clear in my head.

How: I whip out a pen and paper and jot down the first few answers that come to my head to the question “Why do I want to travel to X?”.

For example: Because I’m fascinated by a particular aspect of history/culture, because I don’t know anything about it, because I’m afraid of it, because seeing X or doing Y is on my bucket list, because I need a break and I just want to relax or even just because it sounds awesome!

Visualise Success:

Why: Helps turn the Why Statement into tangible goals/outcomes that I can begin to plan around.

What: Usually no more than 5 or 10 tangible goals / outcomes that would make the trip a success.

How: Back to pen and paper. What would it take for me to look back on this trip and go “Boy, that was an incredible experience, I’m glad I did that!”

For example: I visit, try, learn, taste, meet, master, feel etc… X, Y and/or Z.

2. Identify barriers

Why: Because turning up to hike in rainy season, straying into a war zone, catching malaria or arriving in Ho Chi Minh city on the first day of Vietnamese New Year (when everything is shut for a week) all suck (and are easily avoidable with some quick research).

What: Visa issues, weather and disruptive festivals / holidays are the big things I look out for. I’m a bit more relaxed on health and safety – I’ve spent amazing weeks in e.g., Guatemala or the Northern Border or Afghanistan when government websites would have you believe you’ll be shot or kidnapped the moment you cross the border.

How: There are tons of resources so Google is my friend here, especially for really local or more unusual trips (like overland travel). I’ll always preference recent accounts of e.g., border crossings from other travellers over official government websites.

For Visas I’m a big fan of VisaHQ. For weather check out Best Time to Go. For health risks / vaccinations see IAMAT.

If you really want to unnecessarily terrify yourself then ask the U.S., Government for its opinion on anywhere else.

3. Download or gather links to travel information

Why: Because having these to hand or making them available offline makes it easier (and so more likely) that I’ll read them in the little 5 – 10 minute gaps that crop up in my day or to refer to on the road.

What: There’s a host of great travel information websites on the internet. Here are my go to sources…

CIA World Fact Book – updated annually and full of amazingly detailed facts and statistics for almost every country in the world.

Lonely Planet – is my personal go-to brand of guide books for travel, I buy the PDFs from their online store and especially love the front (top lists, itinerary ideas) and back (cultural and historical overview) sections of their books. Other major options I know of include Rough Guides, DK Eyewitness Travel Guides and Marco Polo Pocket Guides. There are also some great alternative if you speak other languages (especially German).

Wikipedia – has been my first point of call for mostly accurate information as long as I can remember

Wikitravel / Wikivoyage – despite being more prone to error than Wikipedia, these sources usually have a more digestible overview and lots of practical advice (like how to travel to/within the place you’re visiting). Their content is mostly duplicated these so I’ll pick one or both.

Top 10 lists (Google) – Travel blogs and travel agent websites are a wealth of information. I’ll spend a few minutes on Google searching for things like “top sights in” or “best undiscovered secrets of” and pick one or two of the best for more reading.

Itineraries (Google) – As above for “X weeks in Y” or simply “Y travel itineraries”. I find the websites of high end travel agents like Audley Travel perfect for this.

How: I’ll usually save these down as PDFs to a folder in my DropBox. In Safari on a Mac I prefer to Print (File > Print or Command + P) and then save as a PDF (bottom left corner of print dialogue). I don’t know why, my gut tells me I’ve found the built in export function a bit dodgy.

Bonus: If you have a Mac, this little location info script quickly opens four tabs in Safari for the Wikis and Trip Advisor for any location you input.

4. Do background reading

Why: Learning about the country and putting it into a little bit more context (historically and geographically) totally transforms the experience of travelling for me. Not only does it help with the planning stage but it gives my mind lots of hooks to hang my experiences on when I’m there and primes me to look our for and understand things I might otherwise totally miss.

What: Most of the information gathered so far.

How: Just a quick skim through over everything to give myself a feeling for the country at this stage. As I learn more about my target destination I’ll usually be frequently revisiting and updating my Why and Success statements to reflect any new learnings and ideas.

N.B., I really like to revisit this information when I can during and at the end of my travels – it’s amazing the different things that stand out from the text at each different stage depending on the things I’ve seen and experiences I’m having.

5. Synthesise a “Top 10” list

Why: Even if I tear up my plan or do something totally different, having this list subconsciously in the back of my mind is great for spotting and taking advantage of opportunities to get at it.

What: Usually many more than just 10 places I’d like to see and experiences I’d like to have. My risk of “box ticking” (just visiting a place because I “should”) is much lower if I’ve done the first few sections of this checklist properly – a list without some decent Whys behind it always feels shallow and uninspiring to me.

How: Pen and paper or a text file on my computer.

An amazing additional source for these are local friends and fellow travellers. A good friend of mine had the great idea of asking friends she makes on the road for their top local recommendations for wherever they’re from. Then she saves/stars these locations on Google Maps. When she arrives in the country she already has hundreds of local-only sights, restaurants and experiences to hand!

6. Plot “Top 10” list on Google MyMaps

Why: Seeing everything I want to do laid out on a map is an incredibly powerful clarifying experience for me. It suddenly makes distances very real as well as highlighting interesting facts like “Oh, 90% of the things I want to see and do are over here”, “So seeing that means a 900 km detour to the West” or even prompting questions like “I wonder what’s over there?”.

What: Here’s an example of 3 Days in Tokyo (also below) or a basic “Top List” dump of Taiwan

3 Days in Tokyo: Google MyMaps
Three days in Tokyo, planned on Google MyMaps

How: Though I used to use apps like Pocket Earth or Ullman, I’m now almost exclusively a huge fan of Google’s MyMaps – it amazes me that this kind of tool is available for free! The interface and customisation options are very intuitive and Google frequently roles out updates and improvements.

I use the desktop version to quickly create and customise the maps which can then be easily accessed and made available offline on my phone via the Google Maps app when I’m on the road.

7. Draft an itinerary

Why: Picking a rough order for my route has important implications like entry / exit points and can highlight early logistical nightmares (like crossing large bodies of water and mountain ranges). It’s also a requirement for some of those more tricky visas.

What: As simple as a few bullets to roughly shape out my journey, possibly with some initial guesses on how long I might spend in or travelling between each location.

How: My Google MyMap + a pen and paper / Google Docs (if collaborating) / favourite text editor.

At this stage I’ll also go back over any third party travel itineraries I’ve downloaded (like Audley Travel) to check if I’ve missed anything major. I also find it a great time to once again revisit my Why and Success Statements to make sure I haven’t strayed too far from the original purpose of my trip (or to update it)!

8. Firm up itinerary

Why: Because a quick, early reality check can help save a lot of hassle, expense and disappointment down the line. I’ve found this doubly true when distances are large or travelling during busy seasons (e.g., music/cultural/religious festivals or seasonal events like seeing the Cherry Blossoms in Japan) when tickets, accommodation or travel options might be tight.

What: I usually sense check two things at this point:

  1. Travel times – this where spotting things like the option to take 3 busses over 24h vs. one 2h long flight can reshape my draft itinerary
  2. Booking requirements (tickets, travel and accommodation) – the need to book things in advance varies hugely depending on where and when I’m travelling

I try to leave things as open as possible so if I can I generally won’t book anything except flights much more than a few days in advance.


I’ll often use the resources below to make any major adjustments to my itinerary. I’m a heavy calendar user so at this point I’ll put where I might be each night and any travel bookings I’ve made into my calendar so that it drops into my productivity system and gives me an overview of how it fits into my wider travel plans.

Air Travel: I use SkyScanner‘s calendar functions to spot any savings by shifting my entry/exit dates. Other options include Kyak and Expedia.

Land Travel: GoogleMaps for a rough estimate. Then Lonely Planet, Wikitravel/voyage and lastly Google to hunt down any local travel resources like train and bus time tables.

Accommodation: My reading and travel guides have usually given me a pretty good idea of how far in advance I’ll need to be booking. Couch Surfing, Hostel World, AirBnB and Booking.com are all great resources to double check depending on budget, location and availability.

10. Look back on the trip

Why: Aside from the fact that active recall is a critical step in learning effectively, reflecting on the lessons we’ve learned and sharing impressions or war stories from travel is one of its greatest joys.

Taking the time to look back on all or even part of a trip is perhaps one of the most important and yet most overlooked steps in travelling. I’ve found time and again, if I take the time to do a good look back within a week or two of finishing a trip (which I don’t do nearly as often as I should), that the amount that I learn and remember from the trip increases hugely.

What: I tend to use the following six questions as thought starters for my look backs but whatever works for you is the thing that’s best:

☐ What did I do? What didn’t I do?
☐ What did I learn? What was surprising?
☐ What went well? What would I do differently?

How: Wether it’s regularly during the trip or just once a few days or weeks after your return whatever tool you find easiest is probably the best one.

Pen and paper, a diary or your favourite digital note taking tool are all great options. Writing a blog or sharing email updates with your friends and family whilst you travel is another great way to get some of this stuff out of your head whilst it’s fresh.

Not much of a writer? Make time to share impressions and war stories with your travel buddies or even just people you meet who have travelled to the same places over a drink or some food!