For years, I was the guy selling the dream: Leave your 9-to-5, book a one-way ticket, and build something from your laptop while sipping coconut water in Bali. And for a while, I did just that.
I walked away from a six-figure job in corporate America, burned out, disillusioned, and hungry for freedom. I landed in Ubud, then Lisbon, then Medellín. I launched projects from co-working spaces with infinity pools, made deals over sunset mojitos, and lived the lean, location-independent fantasy that’s all over your Instagram feed.
But here’s the plot twist no influencer puts in their captions: after five years of chasing freedom, I’m going back to a cubicle.
And honestly? I’m excited about it.
The dream worked—until it didn’t
Let’s get one thing straight: the digital nomad lifestyle can work. It worked for me. I bootstrapped two startups, built a newsletter that hit 100k subs, and met some of the smartest misfits and builders on the planet. I proved to myself I didn’t need a boss to survive—or even thrive.
But somewhere between year three and year five, the dream started to feel… thin.
Every city began to blur. Every co-working space felt the same. Conversations at cafes revolved around crypto, conversion rates, and content funnels. Even the sunsets started to feel like reruns.
I wasn’t just lonely—I was rootless. Untethered. And for a guy who used to mock the idea of a 9-to-5 routine, I found myself craving structure like a junkie.
Freedom is overrated (sometimes)
Here’s the unsexy truth most digital nomads won’t tell you: freedom without direction is just chaos with a passport.
When every day is a blank canvas, it becomes surprisingly easy to do nothing meaningful with it. I had the freedom to build anything, but also the freedom to endlessly tweak logos, obsess over productivity hacks, or “research” markets until I forgot what the original idea was.
Meanwhile, my friends back in corporate jobs? They were executing. They were building skills, getting promoted, and—brace yourself—some were even happy.
At first, I called them suckers. Now I call them smart.
Why I’m going back
I’m not crawling back to a cubicle in shame. I’m walking in with clarity.
I want mentorship again. I want to be part of a team. I want feedback that isn’t just a thumbs-up emoji in Slack. I want stability—not because I can’t survive without it, but because I finally understand the value of trading some freedom for consistency.
And let’s be real: not all corporate gigs are soul-sucking anymore. Remote work, async teams, flexible hours, mission-driven companies—they’re not unicorns. They’re hiring. The landscape has changed, and there’s real opportunity to work on cool stuff with people, without having to give up your soul (or your sanity).
This isn’t a failure—it’s an evolution
People love to romanticize escape. They turn quitting into a badge of honor. But what if the real badge is knowing when to come back?
I still believe in startups. I still believe in freedom. I still believe in hacking the system. But I also believe in seasons—and I’m in a new one now.
I don’t regret leaving corporate America. That journey taught me everything I know about resilience, autonomy, and building from zero. But I also don’t regret coming back.
Sometimes the bravest thing isn’t jumping off the cliff—it’s knowing when to climb back up and choose a different path.
And for now, that path leads me back to a cubicle—with a little more wisdom, a stronger WiFi connection, and absolutely zero regrets.
