The Scenic Route

Paul Graham is an inspiration. It seems he’s written an articulate, helpful essay on virtually every topic that every topic that a young student, programmer, or entrepreneur would need to know. Perhaps his algorithm is to write to a younger version of himself?

In any event, I’d like to share some thoughts about career management, provoked by a great Paul Graham essay on the topic. I don’t pretend to have all the answers, but I’ve had something of an unconventional path through life, and I have never written publicly about the details. My hope is that others may benefit from my perspective.

Here’s an abridged version of the path I’ve taken to my career:

My Path

I grew up in a household that prized education and entrepreneurship. My grandfather embodied these values and passed them on to my father, and then to me.

My dad was a software entrepreneur, and so, like any self-respecting young man, I grew up planning to be completely unlike my father, the very definition of “uncool.”

I was a math nerd from a very early age, up until when I was bullied in high school. The experience inspired me to leave STEM to try and crack the code of being “cool.” Running far away from the path I had been on, I embraced the humanities, studying in China and dreaming of working for the CIA one day.

After spending a year at GWU studying International Affairs, I realized that I’d chosen the wrong field, my father went bankrupt, and I dropped out of school.

I sold auto parts for a while, but realized it was a dead-end career. I then became a professional DJ, which taught me the incredible lesson that work can be fun! But the choice between artist and wedding DJ made me realize that there must be something out there with higher career potential that was less “subservient to the subjective and fickle tastes of the masses.”

My search led me to computer science classes at community college, as I’d always had a knack for mathematics and was very comfortable with computers, a gamer since age 3. However, I didn’t fully commit to computing until I completed the final project of my CS101. Given the freedom to design my own project, I made a game of Connect-Four.

My techniques were primitive, but it’s hard for me to describe the feeling that I had when I sat down and played the game for the first time. An animation and sound played on victory, and I felt, for once, like I had breathed life into something. This was no longer a bunch of programming instructions, it was a semi-intelligent creation with its own primitive personality! Most interestingly, I had called upon the left brain to design the logic and the right brain to design the animations.

From there, I was in. Before that, I had known that computer science granted opportunities to get a job or start a business. However, I had grown up thinking that programming was a boring task, relegated to cubicle farms full of soulless programmers, all marching to the beat of the drum.

Instead, building Connect-Four taught me was that there was room for CREATIVITY and EXPRESSION in programming. The thought of a career where I could bring art and science together, either for a job or on my own, cinched the deal for me.

Bouncing Around

When I dropped out of school, I felt an incredible amount of shame. All my peers were soldiering onward, so what was wrong with me that I couldn’t hack it?

To add insult to injury, those kids who thought decided in middle school they’d become veterinarians seemed to be having no trouble, eight years later.

I’ve mostly gotten over this shame, but I’ll confess that, even in 2017, 9 years since making that Connect-Four game, I’ve had plenty of moments of failure and self-doubt.

Paul’s wisdom on the topic (emphasis mine):

Some people are lucky enough to know what they want to do when they’re 12, and just glide along as if they were on railroad tracks. But this seems the exception. More often people who do great things have careers with the trajectory of a ping-pong ball. They go to school to study A, drop out and get a job doing B, and then become famous for C after taking it up on the side.

Phew! What a relief.

I always hear about the “10,000 hour rule” and the argument that it’s the purebreds, the deep specialists that win in our modern economy. There’s been a chip on my shoulder for a decade that I’m the reject, the drop-out, the failure.

Certainly, it’s been incredibly helpful to work on my own psychology as of late, but it’s still reassuring to hear Paul’s wisdom, seemingly directed straight to me. And hopefully to you, too!

Finding What You’re Meant To Do

Still, you may want some advice on exactly how to bounce around like a ping-pong ball.

Paul’s later essay distills the criteria down to a single line: “What Doesn’t Seem Like Work?”

In order to keep yourself honest as you move towards the thing that doesn’t seem like work, Paul endorses the (very wise) approach of staying consistent and producing, even small bits of your craft, as you live your day-to-day life:

“Always produce” is also a heuristic for finding the work you love. If you subject yourself to that constraint, it will automatically push you away from things you think you’re supposed to work on, toward things you actually like.

I’ve personally found this incredibly liberating as I much more deeply enjoy working in Clojure and on Linux than in Objective-C on iOS/Mac OS, for example. A younger me was too afraid of moving away from the market into an esoteric discipline, but it’s giving me great joy, building a deeper skillset, and I feel it’s steering me in the right direction.

Building a Career

Now that you know what you’d like to do, how to build a career around it?

In Paul’s opinion, you have these two routes:

  • The organic route: as you become more eminent, gradually to increase the parts of your job that you like at the expense of those you don’t.
  • The two-job route: to work at things you don’t like to get money to work on things you do.

I love the explicit discussion of this choice. I know SO many people who are dreaming of going and doing the “other thing” but are stuck in a different career! He does an excellent job weighing the merits and pitfalls of each.

I want to draw your attention to his (very astute) caution to those people who plan to work on Wall Street for ten years and quit to become a novelist:

Constraints give your life shape. Remove them and most people have no idea what to do: look at what happens to those who win lotteries or inherit money.

Amen. It’s so easy to float around in life. Constraints breed creativity. George Lucas did his best work when he was strapped for resources. It’s not a perfect parallel, but, I was MUCH happier and more productive after leaving a well-paying job at Google to toil away on a pre-funding startup.

Paul’s parting words leave things on uplifting, albeit stoic, note:

Whichever route you take, expect a struggle. Finding work you love is very difficult. Most people fail. Even if you succeed, it’s rare to be free to work on what you want till your thirties or forties. But if you have the destination in sight you’ll be more likely to arrive at it. If you know you can love work, you’re in the home stretch, and if you know what work you love, you’re practically there.

So, don’t give up. When in doubt, give yourself a lift! I recommend The Alchemist, Zig Ziglar’s recordings, and these Paul Graham essays.

Other Materials

There’s a war between “Follow your passion” and “So good they can’t ignore you” that warrants another post.

For now, I’ll leave you with these three strong recommendations:

Parting Words

Jeff Bezos likes to speak about a “regret-minimization framework” for making life decisions. Next time you’re faced with a heart-wrenching life decision, why not ask yourself, “Which of these options would I regret taking? Which would I regret NOT taking?”

I’ve found it works every time.

Written on June 24, 2017

David Kay has dedicated his life to the advancement of the technological singularity. He is a serial entrepreneur, working to impact the future of software development and medicine. If you found this article helpful, join his weekly newsletter.