What you should know before taking your gap year (and lessons from mine)

or alternatively:

I took a year off from my tech career and now I won’t shut up about copywriting.

It was probably going to hurt my career. I was fine with that.

The plan was cliché: quit my job, sell my stuff, spend nine months in Southeast Asia. Produce electronic music, read, and maybe code a little. Then find another tech job and pick up where I left off.

Fast forward twelve months. I haven’t set foot on a plane, I created a software product for DJs, and I’ve developed an obsession with copywriting and digital marketing. What happened?

In this post, I’ll share how, despite all expectations, my gap year catapulted my career into a far more exciting trajectory. I’ll debunk two myths society tells us about gap years and share a framework you can use to generate your own life-changing insights, whether you can take a year or a week off. Lastly, I’ll share advice for taking a gap year of your own.

Gap year myths

Society offers us a number of myths about taking long periods of time off, which I believed until doing it myself.

Myth #1: Taking a gap year will set your career back.

How could it not? Look at all you’re leaving behind: a great job, lots of money, advancement opportunities… the list goes on.

You may not do lasting damage, but you won’t move things forward. In the best case you’ll pause, have fun, then pick up where you left off. A little less sharp, a little older, and a lot poorer. But at least you had your “fun”, right?


Gap time can change your life. Gap time can produce unique, maximum leverage insights that are impossible to discover in the heat of daily life. Used well, this time can lead to insights and skills that will elevate your life trajectory onto an entirely different level. Career success, earnings potential, and happiness stand to benefit.

Envision yourself being launched out of a cannon. The angle of the cannon determines how high you’ll go – your life’s trajectory. Your gap year has the potential to increase the cannon’s angle by a few degrees, leading to a trajectory that far surpasses the previous one.

You gap year can adjust the angle of the cannon.

For me, my angle adjustment came from key career insights and breadth skills developed.

I’ve always viewed myself as a career tech employee — bouncing between tech companies, eventually transitioning from engineer to manager. But my career vision is broader now.

During my year, I created a small revenue-generating SaaS product and through it became exposed to Indie Hackers — a community of internet entrepreneurs. And for the first time in my life, entrepreneurship clicked.

Aspirations aside, this has had practical implications. Since I see myself as a business now, rather than just an employee, I’m motivated to invest time in areas I wouldn’t have before, like developing a personal brand, networking, and building an audience. This has already paid off in many ways.

While time off enabled this insight, equally powerful results of gap time are new skills — especially those you’d never develop otherwise. Writing, marketing, and sales are just a few such skills I developed during my year. Even if my career vision were to stay the same, these skills strictly increase the value I bring to any team in the future.

To be clear, I had no interest in these areas prior to my gap year. I accidentally discovered them through the activities I had time to pursue — namely, starting an internet business. They’ve become valuable skills that would have otherwise remained blind spots for quite some time.

This is all to say that the popular view around gap years is false. Gap years do not strictly hinder career growth. In fact, they may accelerate it beyond your wildest dreams. Career and life are not zero-sum.

In this light, staying at a job that prevents you from reaching your full potential might stunt your career more than a gap year ever would.

Myth #2: Gap years are high risk.

There is risk in taking a gap year, but it’s nuanced. It may be lower than you think.

If you’re privileged enough to have few responsibilities (no debt, no partner, no family) taking a gap year is remarkably low risk. There is legitimate risk in depleting your savings, but that’s about it.

Risks around life and career crumble upon inspection — if your gap year is a disaster and you hate it, you can resume your life as it was. You can always move back to where you lived. If you leave your job on good terms, you can often get it back. Yes, it will be inconvenient. But “rolling back” your life is more doable than you think.

Not only is there little risk in taking a gap year, but there’s actually high risk in staying with a cushy job you’ve thought of leaving. Cushy jobs have opportunity cost. Every day you stay is another day you’re not making progress toward your life-changing insight. And the longer you wait, the less time you have to exploit that angle adjustment.

Gap years have opportunity cost also, but it’s predictable. For most jobs, you can predict the projects you’ll work on, the skills you’ll learn, and how much money you’ll make. On the other hand, the opportunity cost of a cushy job is wildly unpredictable. 

In this case, a gap year is a low risk, high reward bet. On one hand, for comparatively little risk, you have a very real chance to transform your life. And on the other, for perhaps more risk than you think, you have a comfortable, predictable career progression. 

Given how much is at stake — a life-changing insight that may radically transform your life trajectory — how much are you willing to bet that you won’t have that insight, given a year of time and space?

Even if it doesn’t pan out, and you end up in the same position as before (you won’t) — how much are you willing to bet that you’ll regret the experience?

Back to reality. Most people cannot roll back their lives so easily. The good news is that you don’t need to go to such extremes as quitting your job or moving far away. You can mitigate risk and get many of the benefits of a gap year by emulating the core components of one. More on that next.

These are the gap year myths. Not only is a gap year less risky than you think, but the insights and skills you develop during it may accelerate your career beyond your wildest dreams — far more than staying at your job would.

How to engineer a life-changing insight

So, what goes into a productive gap year? Do you really have to take a year off? Do you have to spend thousands on flights? Do you need to spend a year meditating in silence?

No. But, to generate the insights that make it a worthwhile investment, you can’t spend your time any way you’d like. Not any old gap year will do the trick.

In order to generate the maximum leverage, life-changing insights, you need to include three practices into your gap year.

Practice 1: Disconnection

The base requirement to generate a life-changing insight is disconnection.

Disconnection is turning off auto-pilot. It’s detaching from the hectic, everyday, short-term mode of thinking and rediscovering the ability to clearly think long-term. Life-changing insights are long-term insights.

To disconnect, you need to change your environment. A physical environment change can be helpful and is easily achieved with travel, but because disconnection is ultimately a mental shift, it’s far more important to change your mental environment. To do so, you need to create space — from work thoughts and as many mundane life concerns as possible.

The best way is to cut and rebuild. Quit your job (or take leave) and cut everything you can from your schedule. Then rebuild a media diet and hobby pursuits that engage your mind in fresh ways. You cannot uncover blind spots by thinking in the ways you’re used to.

We’ve all experienced disconnection after taking much-needed time off. The problem is that as soon as we find it, our vacation is over and we dive back in. A week off merely breaks the seal.

The first step towards generating your life-changing insight is to disconnect and stay disconnected.

Practice 2: Introspection

Introspection is being self-aware enough to recognize an insight when you see one.
Disconnection puts you in the state of mind for having life-changing insights, but without introspection we run the risk of letting them slip. Insights don’t advertise themselves loudly.

The critical quality of introspective time is lack of stimulation. Insights are lost because we’re constantly stimulated by our work, the media we consume, and interactions with family and friends. Even a mind that’s disconnected from short-term thinking is cluttered with static.

The solution is simple: force yourself to spend time alone and without stimulation. Meditation is the classic way to achieve this but I’ve found light exercise (walking, cycling) to produce the best results. Stream of consciousness mind-mapping and journaling have also worked. 

In theory, this might be enough. Disconnection removes the auto-pilot that hinders long-term thinking and introspection makes us open to insights when they arise. But in practice, it helps to include one final activity.

Practice 3: Exploration

Exploration is any kind of learning, executing, practicing, experiencing, or doing that provides positive mental stimulation.

We need this because it’s hard to generate something from nothing. Most of us aren’t able to quietly sit and produce a life-changing insight out of the blue — we need a catalyst.

Think of yourself like an insight-generation machine. You have the potential to generate amazing insights, but without a spark, you sit idle.

Exploration is the spark. Be it mental or physical, exploration provides the input that puts you in motion and begins the feedback loop. You explore, providing input into the system. Your brain chews on the experience, generating an insight. The insight influences your exploration, generating more experiences, and off you go.

Almost any activity will do. The only requirement is that it makes you think.

For me, it was pursuing a side-project that ended up turning into a foray into building a business. This provided a rich set of experiences that ultimately led to my personal insights around entrepreneurship.

You can think of these three practices like starting a bonfire indoors.

  • Disconnection is the wood. It is the foundation. The base fuel required. You cannot generate a life-changing insight if you’re stuck on auto-pilot.
  • Exploration is the spark that ignites the wood — the activity that puts the system in motion.
  • The insight is the smoke that rises up from the fire.
  • Introspection is the fire alarm on the wall that goes off when it detects smoke. It is your way of knowing when you’ve stumbled onto something good.

The cost of an insight

These are the three required practices to produce an insight. You can apply them whether you can take a year, a month, or a week off. And you must apply them whether you travel the world or stay at home.

However, not all insights are of equal value. Insights have a cost — to be paid in terms of the three practices. The maximum impact, life-changing insights will have a higher cost and demand a higher degree of disconnection, exploration, and introspection than a lower quality insight.

This explains the intuition that a weekend isn’t enough time off to change your life, but a year might be. And it’s within this context that we can answer common questions about time and travel.

Do I really need to take a year off?

Having a year of free time is not a direct requirement for an insight. But in order to have enough disconnection or exploration to afford a life-changing insight, you indirectly need time to:

  • Disconnect fully
  • Explore and pursue an activity for a long enough time
  • Or meditate, reflect, journal and introspect.

Or, in my case, you need time to allow yourself to even pursue a project that you would not otherwise pursue if you had time constraints.

My gap year intention was to explore music making, not entrepreneurship. If I had a strictly limited time window, I would have prioritized that time differently, and never gone down that path, missing out on all these insights & skills. It was the surplus of time that allowed me to not feel bad about going down that route and seeing where it might lead me.

You may be able to train yourself to disconnect in less time. Or work more efficiently to explore faster. But at a certain point, you can’t rush or force these things — you just may need time.

Do I really need to travel?

No. Like time, travel is not a direct requirement for insight generation. That said, it can be a useful tool in order to:

  • Buy yourself more free time by living somewhere cheaper
  • Foster exploration by going somewhere with rich experiences
  • Foster disconnection, introspection, and focus by going somewhere quiet and isolated

Be wary that travel can be a double-edged sword. If your goals are to explore via deep work, the mental overhead incurred by travel may be more distracting than it’s worth.

If you aren’t in a position to travel, that’s ok! I think non-traveling gap years are underrated. I had planned to travel but a medical condition forced me to abandon those plans. I ended up moving in with a parent and had the most productive year of my life. Don’t underestimate the power of a familiar and distraction-free environment.

Unlike time, travel is not even indirectly required by the framework. It’s merely a tool with pros and cons.


I’ll close with some parting thoughts and advice for taking your own gap year:

  • Many people will ask you about your goals or intentions for your gap year. It’s ok to not have a specific answer. It’s ok to merely have a sense that something could be there— you just need to watch out for it along the way.
  • There will be self-doubt. My best advice is for this is to be able derive from scratch your reasoning behind your gap year and to do so regularly. When you feel lost, you can ground yourself in this strong sense of purpose. And if you’re lucky enough to have an open-ended gap year, this reasoning will help you decide when to wrap it up. You’ll be able to tell if you’ve achieved what you set out for. Don’t start your gap year without a clear answer to “why am I doing this”.
  • Don’t discount pursuits or projects that don’t seem aligned with any intentions you may have.
  • It’s easy to forget how you’ve been spending time. Keep a daily journal. Also consider tracking your time on a per-project basis using a system that can generate analytics like Toggl. I wish I had done this from the start.
  • Even without a full-time job, you won’t have time for everything. You’ll still need to manage your time to fit everything into your time constraints.


Society tells us that taking a gap year will stunt your career. This is false. Insights and skills you develop during a gap year have the potential to accelerate your career far beyond what staying at a cushy job could. Gap years may also be less risky than you think.

That said, not any gap year will produce the insights needed to change your life. By including three specific practices — disconnection, introspection, and exploration — you can systematically engineer an environment that most conducive for having a life-changing insight. You can apply this regardless of the amount of time you’re able to take off from work.

Not all insights are of equal value. High quality insights have a cost — to be paid in terms of the three practices. Life-changing insights don’t come cheap. A full year off is not strictly required, but some amount of time is. Travel is not required and is merely a tool you can apply based on your circumstances.

My gap year changed my life. If you’ve been thinking of taking time off, I whole-heartedly encourage you to do so. I doubt you’ll regret it.

To quote the original gap year taker himself,

“I learned this, at least, by my experiment: that if one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.”

Henry David Thoreau, “Walden” (1854)

Honestly, I’m writing more about software than anything these days, but if you’d like to keep up, then follow me at @offlinemark.

I also have a mailing list, where I publish drafts and other thoughts (still figuring it out):

Thanks to Jeff Chen, Nick Costelloe, Yashar Nejati, and Julian Shapiro for reviewing earlier drafts of this post.

Any thoughts?