I need to tell you something about the plan that nobody puts in the spreadsheet.
You can optimize your savings rate, sequence your accounts, hit the tipping point, and exit cleanly — and still end up lonelier than you were in the job you left. Because the job, whatever its other crimes, was doing something for you. It was handing you people. Ready-made, pre-selected, there when you showed up on Monday.
When you leave — by choice or necessity — that social infrastructure disappears with the paycheck.
Most people discover this on the other side, after they’ve already made the leap. I’d rather you know it now.
The job was also your social life
I was at the same firm for seventeen years. That’s seventeen years of lunches, hallway conversations, the shared language of a team that’s been through bad quarters together. The social fiber of my work life was built into the building. I didn’t have to build it; I just had to show up.
When I stopped showing up, I had to face a fact I’d been postponing for years: I didn’t really have a life outside that building. Not in any full sense. I had family. I had a few friends scattered across time zones who I talked to less and less as everyone got busy. But the rich daily texture of belonging — the people who knew what you meant without the context — that lived almost entirely at work.
If this is uncomfortable to read, I think it’s because it’s true for more people than admit it.
Why adults stop making friends
There’s a reason this happens, and it’s not laziness.
Making friends as an adult requires two things most adults have been trained out of: showing up to the same place repeatedly without a specific reason, and being willing to be seen without your professional credentials in hand.
At 25, you have structural opportunities for this everywhere — classes, sports leagues, a neighborhood where everyone is also 25. By 45, the structures have mostly dissolved. You’re busy. Your weekends fill with logistics. The people you’d naturally befriend are behind the same walls you’re behind.
What the job provided — common purpose, repeated contact, low-stakes familiarity over time — is exactly what adult friendship requires, and it’s hard to manufacture from scratch unless you go looking for it.
Most people don’t go looking. They assume friendship is something that happens when conditions are right. So they wait for the conditions, and the conditions don’t come.
What I found in Lisbon
When we moved to Portugal, I wasn’t expecting this part.
The expat community there — and especially the particular corner of it that’s attracted to Lisbon in recent years — is disproportionately people who’ve made some version of the choice I made. Left a career. Started something. Traded certainty for meaning. They’re founders and freelancers and early retirees and people in mid-career pivots, and they’re unusually honest with each other about it because nobody has the same backstory so you can’t pretend.
In two years, I had more real friendships than I’d built in the previous fifteen years combined.
I don’t think it was Portugal specifically. I think it was the specific act of being in a place where everyone was also figuring it out — where the credential and the job title weren’t doing the heavy lifting of the introduction. You had to just be a person. And it turns out I like that.
Coming back to California, I’ve had to relearn the lesson: community doesn’t install itself. You have to go build it.
This is not optional
I want to say this plainly because the FIRE community doesn’t say it enough: community is not a nice-to-have at the end of the financial journey. It is load-bearing. The research on this is as consistent as any in social science. The people who thrive in non-traditional life structures — early retirement, location independence, career pivots — are the ones who built communities around their next chapter before they left the last one. The ones who didn’t are the ones who go back to work not for the money, but because they can’t stand the quiet.
The goal isn’t to abandon ambition. It’s to make sure the life you’re building is actually livable — which means populated with people you’d choose, not people assigned to you by org chart.
This week: audit the column
Here’s the question to sit with, and one concrete action:
Draw a line down the middle of a page. On the left: every meaningful relationship in your life right now. On the right: where each one came from — work, neighborhood, a specific activity, something you chose or something that chose you.
If the left side is thin, or the right side shows “work” next to most entries — that’s not a judgment. It’s information, and it tells you exactly what to build.
One action: find one recurring thing, in person, where the same people show up every week. Not an event. A recurring thing. Book club, pickup basketball, a local hiking group, a community garden, a class. Recurring contact plus common activity is the whole formula. Everything else is just conditions.
The financial work buys you the time to actually do this. Don't wait for the leap to find the people.
Next Tuesday: the question I get asked more than any other — should I try to pick individual stocks? Here’s my honest answer, including the one time I did it right, and what it actually took.
Reply and tell me: When you imagine the life after the financial work is done — who’s in it? Is the answer clear, or is it the part of the picture that’s still blurry?
— Ashleigh