Paul Rosania

Hi! I'm Paul. I work at Slack.
You should follow me at @ptr.
I can also be reached at paul@rosania.org.

The Slow Death of the Young Entrepreneur

August 07, 2013

I wrote this essay in October of 2011. At the time, the emotions were too raw for me to share it beyond close family. As I approach 30, I'm releasing it in the hope that it's helpful to anyone going through this strange and bewildering transition.

On August 28th, 2011 I celebrated my 28th birthday. There was not much fanfare.

Two months later, I find myself unable to sleep. I stare at the ceiling while my mind races. I toss and turn during the night. I snooze my alarm until the last possible second. When I'm not working, my mind is racing with questions, like: What am I doing here? Am I on track? Are my life goals realistic? Does my perception of my self match up with reality? Am I too ambitious? Am I working hard enough? Too hard? I've begun to wonder: am I running out of time?

When I was younger, I thought of my life in stages:

  1. Work your ass off for someone else, learn. (Age 22-27)
  2. Start your own company, work your ass off, get your "fuck you" money. (Age 28-32)
  3. Relax a little. Travel. Get married. Get back in shape. (Age 33-34)
  4. Start a family. Work hard, but for a stable number of hours. (Age 35+)

Today, I'm still clinging to an ambitious set of personal goals:

  • Become an expert engineer
  • Lead a startup to marketplace success
  • Live a healthy lifestyle and get fit
  • Earn financial freedom
  • Build a family
  • Travel

And yet, despite my best efforts, here's how "the plan" has actually played out:

  • Age 22-23: Worked my ass off for a failing startup, had no idea what I was doing, learned a ton.
  • Age 24: Met a wonderful girl (and stupidly worried that it was way too early for "the plan.")
  • Age 25-27: Started a company, worked my ass off, had no idea what I was doing, learned a ton.
  • Age 28: Working my ass off for a startup that has real traction!

You could say I've wandered a bit. Still, I'm not that far off from where I thought I'd be. So why is my subconscious torturing me at night? It turns out, I'm learning a lot of scary things as I get older:

  • Planning for things doesn't make them happen.
  • Your body will deteriorate faster than you think.
  • Life doesn't wait for you.
  • The decisions you face get harder to make.

I find myself fighting these lessons, even as I begin to accept they are facts of life. The rest of this essay is an attempt to make sense of these things. These are deeply personal reflections. They may not apply to you, and I won't be insulted if you stop reading right here. I tell these stories mostly as an act of catharsis.

Planning for things doesn't make them happen

My life has taken a meandering path. Part of that is the pure randomness of events. The rest, I'm beginning to realize, is because I do not know myself nearly as well as I've always pretended. When my first startup failed, I had no savings, and I took a corporate job instead of staying in the startup space. I rationalized it as the only logical choice, and a temporary decision while I got my feet below me. It took 2.5 years and acceptance into an accelerator to get me out the door again. During that time, in my head, I was just biding my time until it was the right moment to jump back into the startup world.

Years can pass while you wait for the right moment for something. In grade school and college, I became too accustomed to being on a "track," knowing that if I followed it dutifully and excelled at every juncture, things would work out on their own. It took me 5 years of professional development to realize that following the obvious path was leading me toward a successful but uninteresting career. Quitting my job to start a startup was like ripping off a bandaid. Painful (scary even!) but worth it. Despite the company not working out, I've taken back control of my career progression, and I'm doing what I love.

Your body will deteriorate faster than you think

I graduated high school in 2001 a member of the varsity track and field team. In college, I let go. By the time graduation rolled around, I had no exercise routine at all, and from September of 2005 until November of 2010 I ran a combined total of 10 miles. (That's five years!) When I got back on the treadmill for the first time, running a single mile was so difficult that I had to use the stationary bike for a month instead, until my circulatory system could adapt to the elevated heart rate, and my knees to the constant pounding.

That experience was like a spiritual awakening. Instantly, exercise was a priority for me. I realized that if I didn't push to get in shape right away despite the tremendous difficulty, I might possibly reach a point where the pain was too great and the slow progress too discouraging. How hard would things be at 35, if they were this hard at 27?

Luckily I persisted, but it was my first glimpse at mortality. If I want to throw a football with my kids or chase my grandchildren in the yard, I need to invest in exercise every week for the rest of my life.

Life doesn't wait for you

On June 20th, 2007 I told a friend I'd be his wingman on a group date with his new girlfriend and her friends. We went bowling at Jillian's, a Boston mainstay. I bowled a 60, for which one of the girls teased me incessantly. Despite the abuse, I asked her out and we've been dating since.

I wasn't ready for a long term relationship when I was 24. In my mind, I had another 5 solid years of bachelordom and hard work before I'd even have to think about settling down and making time for romantic dinners and movie nights.

I worried a lot about fucking up the plan. After all, I had read so much about how family and startups don't mix, and how long nights at the office take their toll on relationships. My advice: don't heed that shit, trust your heart. My girlfriend has been the most stable, consistently supportive person in my life.

The decisions you face get harder to make

When my startup unwound early this year, my girlfriend was deciding on PhD programs. (She's getting a Clinical Psychology degree.) Thinking it would be a clean slate, something new and interesting, she picked a school in Chicago and we agreed to move there together.

Two months later I got an email out of the blue from an entrepreneur whose blog I've read extensively, someone I deeply respect. The email led to a call, which led to a series of interviews and a job offer: in Palo Alto, California. Amazingly, my girlfriend thought I should do it, and I ultimately did. It was the hardest decision of my life.

I'm not sure if I made the right choice. I think about it all the time. But the choice itself is not the point. More important is the weight the decision carries. As you get older, decisions involve more tradeoffs. As I lie awake at night, I worry about the even heavier tradeoffs you have to make when you're choosing between your career and spending time with your wife and kids.

So am I running out of time?

Yes and no. Maybe. Sort of. According to my life plan, I have 5 more years of hard work before it's time to settle down. That means I'm more than half done with the "glory" phase of my life.

Life doesn't play out sequentially. I fear the effect of family on my freedom and desire to work marathon hours. I'm afraid of competition from younger startupers, unburdened by the complex aspects of later adult life. I worry that once the personal burdens grow, my aspirations will become impossible.

And yet, despite my singular focus on my professional life while I was young, my personal life advanced. When family comes along, I maintain hope that the reverse will be true. Life is a balancing act. I may never achieve "the plan", but in a sense I've let go of that goal. I have a better understanding of myself and a more profound appreciation for the shortness of life. (As much as one can at 28!) I haven't squashed the fear, but I'm not totally sure I want to do that. Instead, I'm channeling it into my days. It gives me a drive, and purpose.

Thanks for reading.


Does this describe you? Have you had similar feelings or struggles? You can reach me at @ptr or paul@rosania.org. I'd love to hear from you.