How I Took the Learning Gap Year that Changed My Life

6 October, 2021
Self-Improvement; Life

In 2018 I graduated high school.

In 2019 I took a gap year.

It was the best decision I ever made.

During my gap year, I read 75 books, took 15 online courses, and devoured every Howard Marks memo and Warren Buffet Shareholder's letter I could find. I went to conferences and summits as the youngest in the room and I made angel investments into startups.

Travelling to 10 countries, I went from being kicked out of nightclubs with mates in Portugal to using an avalanche airbag on the alpine slopes of Austria to discovering the world's best pizza after skiing head-to-toe powder in Japan.

Through the uncertainties and adventures, I had the most enjoyable learning experience of my lifetime.

In this article I want to challenge what is meant by a gap year. I cover:

  1. My decision-making process and whether you should take a gap year
  2. How I structured the year
  3. My top learnings from the year
  4. What I would change — advice for taking a gap year

1/ Decision-making process

Everyone's decision-making process will overweight and underweight different factors based on personal preferences. My process is not universal. But, if you're insatiably curious, ambitious, daring and have a thirst for knowledge, then my decision-making process might apply to you.

So, what was my motivation for taking a gap year?

Learning — intellectual, cultural, psychological and practical learning.

I used to say that even if I couldn't travel on a gap year, I would take one. That's because I was energised by the multidisciplinary learnings I pursued. This meant that I didn't need an external motivator. It was just a matter of following curiosities and doing what I enjoy.

As a result, when people ask me whether they should take a gap year, the first question I ask is "if you couldn't travel, would you still take it?"

In general, I think that if your sole reason is travel, then you can normally do that during the university break.

2/ Structuring my gap year

Have you ever tried solving a maze backwards?

It's much easier. The path through becomes much clearer.

The same is true for my gap year — coloured through the lens of hindsight, it looks more planned than it was.

But in reality, it was like navigating an open maze. At each juncture, I had to pick one path with the opportunity cost of time.

At the start of the year I wanted to start a business, buy a property, learn Brazilian Jiu Jitsu, become advanced at piano, learn Spanish and the list goes on.

By the end of the year, I did some of these things but the majority, well they're still on my 'to-do' list 3 years later.

My overarching objective emerged organically throughout the year. It was to increase the pace at which I could learn. I took a course on learning how to learn and read nine books on learning.¹

I made it my goal to master the skills that speed up the adoption of other skills — these are the highest leverage activities you can do.

For any pioneering gap yearers, I outline at the bottom of this article how I should have structured my gap year with benefit of hindsight.

3/ Key takeaways

Learning is the most important skill. The fastest learners win. This is because knowledge compounds.

I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. — Charlie Munger

I don't know much. The more I know, the more I realise I don't know. This is called the Dunning-Kruger effect.

The good learn from everyone and everything, the average only from themselves, and the stupid already know everything. — Socrates

Busy ≠ productive. This was my iPhone background during my gap year. It's crucial to have a bias for action and to avoid artificial complexity.

There are two kinds of people in the world: those who say they do and those who do. — Niki Scevak

Projects take longer than you think. I still overestimate the amount I can achieve in a day even when I try to adjust for this. I kept a journal of decisions and predictions I made. Most predictions were correct in outcome, but incorrect in timing — I predicted things would happen quicker than they did.

Fear is a good signal that you are improving. If you're afraid of something, perhaps that means you should do it. A gap allows you to dive into fears, whether it's travelling solo or meeting strangers.

Ironically the biggest antidote to fear is action. Action breeds results. Results show that there is nothing to fear.

Perfectionism is a defensive mechanism. Three anti-perfectionist mantras I implement are:

  1. Good enough is perfect.
  2. Move fast and break things.
  3. Make decisions with 70% knowledge.
Success in life is the result of good judgment.
Good judgment is the result of experience.
Experience is usually the result of bad judgment.

4/ What I'd change

Were I to take my gap year again, there are several things I would change.

I would spend a stint travelling solo. I would heavily plan half of my trip but have no plan for the other half.

I would have tried to actively meet more people. Many of the events I went to were fantastic opportunities to meet people. But I hardly knew what networking was, let alone coffee chats and actively using LinkedIn. A mentor could have dramatically accelerate my growth here.

If I had a gap year today, I could learn 5x (seriously!) what I learnt in 2019. This is because knowledge compounds.

I wish I'd learnt what I since know about curing hangovers and minimising the negatives of alcohol whilst still drinking. I track my liver health through blood tests (yes, I track too many things). It has slowly improved year-on-year since 2017.

If I started my gap year again today, this would be my 4-step roadmap:

  1. Have 2 lunches per week with a stranger (I did zero of these). I would reach out to people from all backgrounds on LinkedIn, using my learning gap year as a premise to have lunch. I would organise these up to two months in advance, and not be afraid messaging anyone.
  2. Go on Meetup and Eventbrite to sign up for one event per week. Pursue whatever is interesting.
  3. Do work experience at 2-3 companies to get exposure to new ideas. Consider VC, investment banking, and startups. I was always afraid to ask for work experience because I wanted to first know enough to contribute meaningfully. I delayed work experience for way too long.
  4. Organise 2-3 trips away, internationally or domestic. Make one of these a solo trip. I would set goals for the trips, even if it were purely a social trip - for example, clubbing can be more fun with goals that add novelty.


Do I recommend a gap year?

It depends on your goals.

If you're like me, I would recommend it without thinking twice. I'd even go as far to say consider halting university for a year to do it.

Warren Buffet likes to say, “the best time to plant a tree was yesterday. The second best day is today”. It's not too late to start learning and nor is it too late to take a gap year.


¹ Books I read on learning:

  1. The 4-hour chef (Tim Ferriss)
  2. Ultralearning (Scott Young)
  3. What Smart Students Know (Adam Robinson)
  4. The Art of Learning (Josh Waitzkin)
  5. Atomic Habits (James Clear)
  6. Mindset (Carol Dweck)
  7. The Talent Code (Daniel Coyle)
  8. Bounce (Matthew Syed)
  9. Deep Work (Cal Newport)

This article is the second in my series inspired by Michael Batko's 3-time rule:

"I set a rule that when I get the same question three times, I find the answer online or write it up myself and put it on my blog."

Here's the first article in this series: "Why I Dropped Law After Coming First in Law".