Dear Coach Jason,
I did it. After grinding for years in Big Tech, I finally quit my L6 engineering job last spring to launch my own thing. The dream, right? Well, it's been a whole year and honestly... I'm freaking out a bit. I've built a couple of apps that went nowhere (like, seriously, maybe 12 users total?), managed to scrape together a few thousand in revenue, and my savings are disappearing fast. I've probably got 10 months left before I've really got to find some kind of job, and in this job market, I'd be lucky to match my old comp.
To make it worse, I hit 30 in October and I'm having a full-on crisis about it. My LinkedIn feed is just a parade of former colleagues killing it at new jobs with fancy titles, while my college friends are buying houses, having kids, or posting from some beach in Thailand. Meanwhile, I'm in my overpriced studio eating the same sad Chipotle knockoff bowl I made three nights ago, wondering where I went wrong. I really thought by 30 I'd have my shit together, you know?
Spiraling in San Francisco
Dear Spiraling,
Oh man. I get it. Your thirties are a really fraught time. You no longer have the same optimism and gusto of your twenties, but you're also not established enough to feel secure in your path like it seems many people are in their forties.
And you're not alone. A lot of my clients are high achievers in their late twenties or early thirties asking themselves the same questions you are, dissatisfied and anxious about the future in very similar ways.
Throughout my twenties, I remember 30 as being this wall. Like I had to make it by the big 3-0. Exited startup. Financial security. Long term partner. Lots of opportunities on the horizon.
The reality was that at 29, I was living in a cramped apartment with three other dudes and only one bathroom, working my second post-startup job that didn't even pay six figures, drained of any savings after fighting a spurious lawsuit, and caught in toxic relationship that gave me no joy. My vision of 30 felt like a dumb fantasy dreamed up by a college kid who had no real idea how the world worked.
But my thirties surprised me. I turn 39 this month and I've finally hit a lot of the milestones I had hoped to reach a decade ago. I sold a company to Facebook. I built a modest retirement account. I got married to a wonderful woman and live in a home we own with our 10 week old baby girl and work a job that is fulfilling, highly independent, and supports our life.
There's a growing body of research around this age, that psychologists like Dr. Clare Mehta are calling "established adulthood" which is the period between 30 and 45 where people develop confidence in their personal and professional lives despite ongoing challenges and transitions.
If your twenties are a time of exploration, of taking risks and making mistakes, then your thirties are where you put your skills and experience to work, you see how the seeds you planted years ago (particular projects, random contacts) pay off in unexpected ways.
In your twenties you are still living the expectations of others (parents, teachers, peers, society), your thirties are where you get to rewrite those expectations and really live for what matters to you.
None of this takes away from the real challenges you're facing. Maybe you need to try a different approach, sell before you build, offer productized services instead of pure software, or just target a market that is more willing to buy (hint other dev's often make the worst customers).
There's a good chance you can pull something off if you are resourceful and stay close to your customer. Maybe you will need to do some part-time consulting work on the side, or yes, even go back to a job with a bit of a haircut on your salary.
But I promise that you aren't falling behind, even if it feels that way.
The truth is, life is more chaotic and challenging in the post-September 11 / Great Recession / COVID-19 era. Americans in the 2020's have accumulated less wealth by their 30's than those in the 1990's, thanks to a doubling of student debt from Gen X to Millenials with income levels being roughly flat. Meanwhile rental and home prices have well-outpaced inflation and healthcare premiums of skyrocketed.
And from a milestones perspective, 67% of Baby Boomers aged 25-37 were married while less than half of Millenials are. American women were having their first birth around 24-25 in 1990, while it's averaging 30 by 2019 and even later for college and grad school educated women. And of course plenty of people are now staying single and childless by choice indefinitely. Everything is getting pushed back, both for economic and cultural reasons.
So Spiraling...as long as you are making an effort to learn, make your own decisions, and operating according to your values, you are building your agency and ability to enact change in the world.
Even if your startup journey ends in utter failure, you will still have gained a valuable experience and will understand that:
- Entrepreneurship is requires skill, effort, and luck
- You can survive a total failure and keep going
Look, success doesn't follow some universal timeline, and honestly, the yardsticks we use to measure it are pretty outdated. What actually matters isn't checking boxes by certain birthdays, but building resilience, knowing yourself, and having the guts to chase what really matters to you. Your current predicament might be painful, but it's also proof you're brave enough to veer off the expected path and test yourself in the real world.
Have a question for me? Reply to this email and you might see your question show up here one day!
