A conclusion, by way of introduction

Back when I carried fat Moleskine notebooks for journals, unwrapping a new one felt like an occasion; I’d always take some time to write a short conclusion for the old journal, and an introduction for the new. Nowadays my notepads are slimmer, and I fill them more quickly; there’s no room for endings or beginnings. But starting a blog does feel like an occasion. And, as it turns out, this introduction hinges on a conclusion. So here we go.

For the past year and change I’ve been up in the air: working at a big tech consulting firm, flying every Monday and every Thursday, every week, for more than a year. If you asked me what I did, the answer on paper is that I was a senior software engineer, with a focus on iOS and mobile applications. But that doesn’t quite capture the gestalt of the life I’d been leading. One of my roommates asked me a few months ago, “What exactly do you do when you’re away all the time?”

“Basically,” I said, “some big company in City X has a thing they need built or a problem they need solved, but they don’t have the right people to make it happen. So we look at our roster and assemble a team, sometimes hailing from three or five or seven cities. Then on Monday morning we all fly to City X, converge on their office, do the job until it’s done and fly home.”

“Huh,” she replied. “Do you wear sunglasses?”

A photograph of the author in business attire and sunglasses
Fuck yeah, we wear sunglasses.

Looking back, it was amazing. I got a paycheck for doing a job I was great at, I got to work on diverse projects with talented people, and I learned a lot about the business world in the process. Sure, the travel grated at times; being away from the people you love is never easy. But in exchange I got the chance to see the country, in a way that few people have the opportunity to do. It was truly a privilege.

And today I walked away from it all.

It’s funny to reflect on the path that brought you to where you are. I went to school for photojournalism, and only ended up in Flash development because everyone was talking about technology in the newsroom. When the iPhone came out I decided to try hacking on the new thing in my pocket. I wrote apps that scratched an itch for me. TweetSheet, the Twitter archive, I remember frantically coding as my account approached 3200 tweets. SmokeBreak, I made to help my roommates quit smoking. Dictapad, the transcription aid, I wrote because I had a ton of interviews to transcribe for my M.A. report.

TweetSheet saw some modest success in Japan, and SmokeBreak brought in modest ad revenue on 75,000 downloads. But these successes didn’t cover even my modest life in New York. So in 2011, with $35 in my bank account, I spent $5 on a MetroCard and headed to a job interview. And that’s how, some time later, I found myself flying around, building apps for companies that I’d previously only read about. Never mind that the work no longer scratched an itch: suddenly I found myself in the midst of building a career. I’d achieved a level of success.

Four travelers walk past a large advertisement telling them to Keep Climbing
Upwardly mobile.

And yet.

Every Monday morning, flying out from Terminal C of LaGuardia airport, I would pass by this really fascinating advertisement. From time to time I’d just stand in front of it, watching the young ambitious consultants and the grizzled business travelers wheel suitcases past in my early morning haze. The ad consisted of a blue wall, 15 feet to a side; a Delta logo; and two words: “Keep Climbing.” For me it felt heavy with symbolism. It was a weekly reminder of something that we don’t always question in the day in, day out flow of work and travel. A reminder that the success you’re looking for is always one level up. Never mind whether this was the success you set out for in the first place.

A few months ago I had an idea. Having an idea can feel a bit like falling in love, and in this case I was ensorceled. Idea forced its way to the front of my mind until I couldn’t not think about it. Notes about idea began to dominate my slim notepads; suddenly I found myself rushing home on the weekends to read obscure technical specifications and scribble down thoughts about idea. More and more I became convinced that I wanted to build idea — and once I was convinced, I realized that I couldn’t do it while flying twice a week and working full-time.

I was faced with a choice: the success I’d found, or the impulse to create that got me started in the first place. To keep climbing, or to scratch the itch. I won’t lie and say it was an easy choice. When I made it last month it felt a bit like jumping off a cliff. It still does. Literally yesterday, I was expensing my cab rides, and tomorrow I’m unemployed.

Still, through all the uncertainty as I enter into my freefall, this refrain keeps playing in my head. Something I told one of my friends as we discussed the pros and cons of taking the leap:

“This idea may not succeed. That’s not a reason not to try.”

So ends the last chapter. Tonight I type in git init, unencumbered.

And I start a new notepad.