My daughter turns one today. This past year I changed jobs, tried to start a company, paid off my mortgage, and moved my family to Japan. I also learned how to change diapers and survive on very little sleep.
Nothing went according to plan. I'm grateful for most of it.
There are a few books that have shaped how I think about decisions — Annie Duke's Thinking in Bets, Nassim Taleb's Antifragile, and the idea of power laws. I keep coming back to them whenever life gets messy. This year was messy. So here's me trying to make sense of it.
I've always made weird career choices
This year wasn't the first time I did something that looked dumb on paper.
Eight years ago, I turned down a software engineering role at a big global consulting firm to take an internship at a small ride-hailing startup. The pay was over 90% less. My parents were not thrilled.
But that startup was growing fast, and I learned more there in six months than I probably would have in years at the consulting firm. Engineers weren't a side function — they were the product. That one decision shaped everything after it. The skills, the roles, the career I have now — it all started with picking the scarier option when I was 21 and had nothing to lose.
Taleb talks about optionality — having more upside than downside. The consulting firm was safe but had a low ceiling. The startup had a lower floor but way more room to grow. When you're young and have no mortgage and no kids, you can afford to take that kind of bet.
I think about that a lot lately, because this year was full of similar choices — just with much more on the line.
Putting family first
Soon after my daughter was born, I stepped away from a demanding senior role. Not because the job was bad, but because I didn't want to be half-present for the early months of her life.
Most people would call that reckless. Maybe it was. But I had savings and enough of a runway to not panic. I'd been careful with money for years, and it paid off when I needed it to.
Taleb has this idea called the barbell strategy — be very safe on one side so you can take risks on the other. My savings were the safe side. Stepping away was the risk. It worked out, but I won't pretend I wasn't nervous.
The startup that didn't work out
With some breathing room, I decided to build something — my second attempt at a startup. I spotted a regulatory trend in the EU, built a real product around it, and talked to real customers.
The idea made sense. The law passed. But the enforcement turned out to be weak — nothing like GDPR. No one felt the urgency to act. I couldn't get funding.
Annie Duke has this useful distinction: don't judge a decision by the outcome, judge it by the process. Was my thinking sound? I think so. I spotted a real trend, built a real product, and talked to real customers. The thing I got wrong — how seriously the law would be enforced — wasn't really something I could've known upfront. That's poker, not chess. Sometimes the cards just don't fall your way.
I learned a ton from it. I'd do it again.
Debt free
This is the boring one, but honestly it might matter the most.
I bought my property during COVID when prices had dropped and most people were sitting on the sidelines. A few years later, the value has nearly doubled. But the bigger deal for me was paying off the mortgage entirely. No more debt.
That house is my fallback. If Japan doesn't work out, if something unexpected happens, I have a home to go back to. It just sits there, appreciating quietly, while I try new things elsewhere.
Taleb talks about via negativa — improving life by removing things rather than adding them. Getting rid of debt didn't feel exciting. But it removed a ton of pressure. Every big decision I made after that — moving countries, taking a different kind of role — was possible because I wasn't scared about money.
Moving to Japan
We moved our family to Japan. Cleaner air, cleaner water, safer streets. It meant leaving behind everything familiar and adjusting to a completely new culture and language.
I kept asking myself the 10-10-10 question from Suzy Welch: how will I feel about this in ten minutes, ten months, and ten years?
Ten minutes: scared and uncertain. Ten months: my daughter's eczema is getting better. She was allergic to egg and reacted badly to heat and pollution back home. Here, her skin is clearing up. She sleeps better. We live in a quiet neighborhood and we're settling in.
Ten years: my kids will have grown up bilingual. We'll have had access to great healthcare and infrastructure. We'll have options we never would have had otherwise.
The trade-offs were real. But they were worth it.
What's next
The tech industry is going through a lot of disruption right now, especially with AI. Things feel uncertain. Taleb has this thing called the turkey problem — a turkey gets fed every single day and feels safer and safer, right until Thanksgiving. I don't want to be the turkey. Comfort is nice, but it can make you blind to what's coming.
So I'm keeping my skills sharp. Slowly, steadily. Not burning myself out, just staying ready. If a good opportunity comes along — a bigger company, an interesting startup, something I haven't thought of yet — I want to be in a position to say yes.
I'm also working toward long-term financial independence. I'm 29, I'm debt-free, and I'm healthy. I have time. Whether it takes five years or fifteen, I'm okay with that. The direction matters more than the speed.
The thing I keep coming back to
If there's one lesson from this year, it's that the order you do things in matters just as much as the things themselves.
Pay off the mortgage before moving to Japan. Save up before trying the startup. Get settled before planning the next move. Each step made the next one possible. None of it was genius — it was just being careful about sequencing, so that if any single bet went wrong, I could absorb it.
To my daughter
You won't read this for a long time. But when you do — every decision we made this year, the scary ones, the boring ones, the ones that didn't work out, we made with you in mind.
You're one today. You're healthy. You're laughing more. Your skin is clearing up. You're in a good home, in a good neighborhood, in a country where the air is clean and the trains run on time.
Not a bad first year.
Happy birthday.