The Pursuit of Happyness: Part II
It’s 2025. Eleven years later, after my first thought on The Pursuit of Happyness, I’m still at it… just with different tools and higher stakes.
I’ve been fully remote, fully distributed since 2015. No office, no commute—just bandwidth and trust.
The money got better. Significantly better than my London employee days. That buys freedom… and a quiet pressure. No one asks you to work nights or weekends. You just might anyway, because the privilege feels rare and there’s a strong output culture. It can turn into a race: who ships more, faster, cleaner. No scoreboard, yet somehow there’s always a scoreboard.
Days blur
Personal life bleeds into work, work stains the evening. Discipline becomes infrastructure. When you’re tired, boundaries fall fast.
I’ve loved computers since I was a kid. Now I can work from the sofa, desk, train, phone… pick your battlefield. You think I’ll stop doing what I love just because the battlefield moved home? Please.
Still, I saw early signs of burnout. A few tough moments at home. Impostor syndrome tapping me on the shoulder. I learned, sometimes the hard way, that rest and boundaries aren’t optional. They’re part of the job.
What I’ve really learned is agency. Hard to translate neatly into Italian, so that’s probably why it was so difficult to grasp it. My unconscious probably still thinks in Italian 🤌🏼
Not freedom in the abstract, but the boring, daily capacity to choose: when to log off, what to say no to, what to ship, what to ignore. Remote work amplifies everything; without agency, you drift. With it, you draw the line, own the trade‑offs, and stop outsourcing your pace to fear or hype.
The upside
Phenomenal people around the world. Wild connections. I’ve seen how different cultures run internal politics, how teams negotiate power, how colleagues think when the Slack tone is polite and expectations can be implicit.
I’ve traveled... a lot. Picked places I actually want to live, not just pass through. Worked from there, stayed longer, paid rent, learned names. Saw different cultures up close while shipping. Chose to feel like a local, absorb a place’s rhythm, and not extract it like a tourist.
Along the way I honed a strange skill: reading body language fast (words carry less meaning when you don’t understand what’s being said). The tones, the shades, the almost imperceptible shifts in how people move or pause. Travel sharpened it. At work it lets me read a room’s temperature in an instant.
Post-Covid momentum
Then LLMs entered the toolkit. Not magic, just big models that help you write code and sentences. Some panic, some euphoria. Still both.
Tools are accelerants: they speed up the good and the bad. I try to use them responsibly, within policy and with review.
Post‑COVID, with layoff waves, pressure spiked.
“Meets expectations” used to be reachable; now it can feel like a narrow gate. Who climbs? Often the ones with extreme focus or unusual talent. Great developers with families are paddling hard to stay level.
Maybe it’s a bubble. Maybe it’s the new OS of work. Either way, it goes beyond tech. The collective fatigue is real.
Meanwhile, a thousand coaches chant: happiness is a journey, not a destination. Others say: don’t attach to companies… attach to a mission, a calling, a purpose. Cute slogans. Occasionally true.
Looking back, the first 6-7 years of remote feel simpler now. Back then I had the constant fear of losing the gig tomorrow. Contracting shifts risk onto workers: few protections, lots of responsibility. Some of that hasn’t changed.
Then the question is: “Is the big paycheck worth it?”
It’s a standing trade‑off between headspace and income.
You pay either way.
What has changed is me. I protect sleep. I move daily. I calendar boundaries. I say no. I log off when my brain turns to oatmeal. I care about high standards, sustainable execution, and team trust. And I keep learning: code, people, systems… and, too often, politics.
Closing
The internet made the world our office. It didn’t make it kinder. So we have to!
See you in 10 years for the next chapter of this saga. Fewer mistakes, better boundaries, same curiosity!