Startups are the new deferred life plan

“And then there is the most dangerous risk of all — spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.”

— Randy Komisar, partner at VC firm KPCB

I was 19 when I read “Are You a Pirate?”, Michael Arrington’s treatise on life as an entrepreneur. In the article, he argues that entrepreneurs are motivated by a unique approach to risk. Instead of avoiding it, they seek it out for adventure, much like the pirates of the 17th century. For them, he writes, risk itself is the reward.

At the time it was published, I was interning as an analyst at an energy company in Philadelphia. I remember sitting in my cubicle, reading the article, and thinking, “This is what I want to do be doing with my life.” I began doing some unpaid work for startups on the side, and within a year, I’d quit my job and was working on a startup of my own.

In the beginning, I was thrilled just to be building something. I loved the idea of inventing the future, and I was excited to have startup friends with whom I could bounce around ideas for changing the world. Sure, I was interested in creating a lucrative business, but like the pirates in Arrington’s piece, the potential riches were in many ways an excuse for the adventure.

Over time, though, things began to change. I compared myself to the people who were “killing it” on TechCrunch, and I began to crave an exit. I started exploring less risky ideas and began looking for the surest path to success. Ultimately, I ended up working on a product that I thought had potential, but that I really didn’t care about, hoping that it would do well enough so that down the line, I could live the life I wanted and work on something I found meaningful.

Ambitious young people are flocking to San Francisco, London, and other startup hubs. Fueled by coffee, Red Bull, and other nootropic substances, they work 80-hour weeks at below-market wages while chasing “unicorns” and “rocket ships. If all goes well, they hope to get a piece of the insane amount of money that is getting thrown around.

This is not so different from the “dream” sold to investment bankers. New recruits work like crazy for their first two years in hopes of eventually becoming partner or finding a job at a hedge fund. If they can make it through the ringer, they are promised tremendous wealth and prestige.

A big part of why I got into startups was a reaction against this mentality. I hated the idea that you should defer what you care about in life, devoting yourself entirely to your career until you’ve reached success. I wanted to enjoy my work in the present, and I didn’t want to sacrifice my youth for a job.

Yet, that’s exactly what ended up happening. As I became more obsessed with getting to an exit, I started feeling guilty whenever I wasn’t working on the business. I began to neglect my health, hobbies, and personal relationships. I stopped working out, ate more fast food, and would cancel plans with friends if I felt I hadn’t been productive enough to warrant social time.

This went on for a period of 6–12 months. I lost any intrinsic joy I had in my work, and it got to the point where I had to drag myself out of the house every morning, dreading the day at the office. I remember lying on my back at the top of the stairs one day, staring at the ceiling and thinking to myself, “Why the hell am I doing this?”

I didn’t have a good answer. I never wanted to be someone who cared solely about amassing wealth and success, yet that was what ended up informing most of my decisions. That values conflict wore on me everyday, and eventually, I just couldn’t continue. I told my co-founder I needed to step back, and after some discussion, we decided to wind down the venture.

For a time afterward, I wasn’t sure what to do. I had some ideas for startups, but I was so burnt out that I couldn’t bring myself to actually begin working on any of them. At the same time, I felt guilty that I wasn’t working. I felt like my life and career were stagnating.

For awhile, I’d been feeling like everything I did had to be on the direct path to success, because I wanted to get there as fast as possible. Then, one day, it hit me — my approach to work was making me utterly miserable.

I realized that given the choice between reaching success in 5 years while hating the day-to-day and reaching success in 20 years while enjoying the journey, I’d rather take the slow road and have some time to smell the roses.

In some ways, this is a false dichotomy. Rarely is it the case that you need to explicitly choose between the fast and slow path, between being happy or being miserable at work. Yet, looking back, I could see that many times I had sacrificed my personal happiness to pursue what I thought was the shortest path to success. I had optimized for that over everything else, and all of those small decisions added up to me feeling incredibly unfulfilled.

Founders and early employees of tech companies often pay a high personal cost. Most of my tech industry friends have gone through major burnout at least once in their careers, a result of a culture that idolizes workaholism. This is heartbreaking, as most of the people I know in the startup world are in their twenties and early thirties — the prime years of their lives.

This is a unique period in one’s life, when you’re free enough to travel the globe with only a backpack or pick up a new hobby on a whim. You can dive headfirst into art, meditation, or a whirlwind romance, and really explore who you are and what you value in life.

Yet, many people I know are spending these years hunched over a computer, thinking of few things besides their company, their career, and how to “make it” in the world. They’ve bought into the same deferred life plan as the 22-year old banker at Goldman Sachs; it’s just sugarcoated with words like “disruption,” “ownership,” and “innovation.”


After I realized that my drive for success had been causing so much stress, I decided to start prioritizing happiness in the present over finding the quickest path to prosperity. Bit by bit, I began to allow myself to pursue things just because they seemed fun or interesting. Over time, I realized that before jumping into another startup, I wanted to spend some time exploring the world and working on side projects.

So, I found some freelance work and bought a ticket to Costa Rica. Along the way, I met a hotel owner who was looking for ways to fill his hotel during the off-season, and ended up pitching him on inviting a bunch of developers and designers down there to work remotely and hack on side projects.

Things snowballed, and eventually, this turned into my main gig: Hacker Paradise (we organize trips around the world for people who want to work remotely or focus on side projects). Through it, I’ve met some amazing people, and in the last year, traveled to places like Vietnam, Bali, Thailand, Barcelona, Berlin, Tokyo, and Taipei (I’m writing this from Vietnam). More importantly, though, it’s gotten me back in touch with the joy of creating things for their own sake.

If you’re out there working on a startup, I’d ask you… why?

Don’t get me wrong; there are good reasons to work on a startup. Startups mean more autonomy than you can get elsewhere, and they can be a great way to learn quickly, gain a ton of experience, and express what you believe about the world. They can be an incredibly effective way to solve a problem, and indeed, there are certain classes of problems that essentially require venture funding.

Still, the beautiful thing about a startup is that there are no rules.

You don’t have to be in Silicon Valley chasing venture money and paying $2,000 for a tiny apartment in the Mission. Instead of building an organization that you hope will buy you happiness in 5 years, you can build one that will bring you happiness today.

And, if you do find yourself dreading the grind and waiting for the day when you can finally start living… throw a wrench in the system.

Move to Paris on a whim. Bike from Hanoi to Saigon while working remotely. Build a side project and then give it away for free. Join a band. Learn a new language. Love with reckless abandon. A startup can be rewarding, but so can all of the above.

The real risk isn’t in getting off the traditional path; it’s in staying on it and missing out on the full range of experience life has to offer.

And, if you do decide to do a startup, keep an eye out for the deferred life plan. Even if you decide to raise money and swing for the fences, you can still find ways to enjoy the day-to-day. Try to build an organization that you’d want to be a part of for 10, 20, or 30 years to come.

I’ll end with one more quote by Randy Komisar from his book, The Monk and the Riddle:

“At key points in my life, I’ve found it helpful to ask myself a simple question about what I was doing at that moment:

What would it take for you to be willing to spend the rest of your life on [it]?”

“Don’t concern yourself with exit strategies.”

(The Monk and the Riddle, p.77, published 2001)


Have a job that lets you work remotely? Thinking about taking time off to work on your own projects? Consider joining one of our upcoming trips to Bali, Thailand, or Portugal.