Do you ever think about moving somewhere different? Switching careers? Pulling the work-life balance back toward life?
You’re not alone. And there has never been a moment when “no time like the present” landed on so many people at once.
The pandemic was a strange teacher. It forced a question most of us spend our whole lives avoiding: is this the path I’d choose, if I were choosing? Some people answered by starting a side hustle. Some moved. Some finally got in shape. Some fell apart. But almost everyone, at least for a moment, was made to entertain the one idea we work hardest to ignore — that our lives, and the lives of the people we love, are not infinite. Things change suddenly. The runway is shorter than the calendar suggests.
What became clear to a lot of us is simple, and a little terrifying: we have more control over our path than we admit, and far less time to change it than we’d like.
That’s the whole reason this exists.
What this is
Breaking Free is a publication about money, time, and the life you’re actually building with them. But it is not a personal finance newsletter in the usual sense.
Most money advice answers the question how. How to budget. How to save. How to squeeze another percentage point out of your index funds. That advice is everywhere, it’s mostly correct, and it mostly keeps you exactly where you are — just slightly more optimized.
The question almost nobody asks is why. Why do you want the house, the title, the early retirement, the number in the account? What is the money for? Because money and time are the same currency in two different denominations, and you are spending both, every day, whether you’re paying attention or not.
So that’s the deal here. We’ll get specific and practical — taxes, accounts, the real math of buying back your time. But every practical piece will answer back to a single question: does this serve the life you actually want, or just the life you drifted into?
Why me
For seventeen years I worked the same job. The pay was good. The work-life balance checked the boxes. And when I pictured myself there in another five years, I felt nothing — because I’d stopped growing. I’d stopped learning. I had quietly become very good at a life I never actually chose.
In the background, something else was growing. I’d spent years researching small, overlooked public companies — the kind almost nobody listens to the earnings calls for. I found other people doing the same thing, and a community formed. Along the way I unlearned a “truth” I’d accepted my whole life: that you can’t beat the market. I watched people who’d been beating it for decades, not in the meme-stock frenzy, but quietly, with patience and homework. One company I’d followed and spoken with for years became a Tesla supplier’s supplier and rose more than tenfold in a few months. The lesson wasn’t the win. The lesson was that the rules I’d inherited were not laws of physics.
Then our second child arrived, and the math of childcare collided with the math of my own time. Two kids in care ran us roughly fifty thousand dollars a year, after tax. I could keep trading my hours for a paycheck to pay someone else to spend those hours with my kids — or I could spend them myself. In 2022, I left.
And then we did the thing you’re not supposed to do. We moved to Portugal.
Here’s the question that move forced: do you have to stay in America to live the American dream — or should we just call it the dream, and admit it’s portable? White picket fences are for sale in a lot of countries. Ours came with safety, affordability, a family-forward culture, and a community of founders, nomads, and people who’d also stepped off the wheel. The only fierce politics here are soccer rivalries.
I’m not telling you to quit your job or move abroad. Most people shouldn’t, and timing matters enormously. I’m telling you that the menu is much longer than the one you were handed.
The one idea everything here is built on
Everything is a trade-off. How you spend your time, how you spend your money, how you treat the people around you and yourself. We are taught to maximize one number — the money coming in — and to treat everything else as what’s left over.
I want to flip that.
Maximizing your time can grow your earnings anyway, while freeing you to build the parts of life that have nothing to do with a balance sheet. The financial gurus who preach pennilessness — make your own cleaning spray, hang your laundry, never hire anyone — are quietly trading the one resource you can’t earn back for the one you can. Sometimes that trade is right. Early on, when time is abundant and money is scarce, frugality is a superpower. But there’s a point where a company is paying handsomely for your time, and the question becomes: shouldn’t you value it at least as much as they do?
That’s the lens. Not “spend less.” Not “spend more.” Spend consciously — every dollar and every hour as a deliberate vote for the life you’re trying to build.
What you’ll get, and when
Two posts a week:
- Tuesday — Foundation. The practical machinery. Budgets, accounts, taxes, the actual numbers. Useful even if you skip every other word I write.
- Friday — Philosophy. The harder questions. What money is for. Why frugality can become its own cage. What to do with the time once you’ve freed it.
They’re designed to be read as pairs. The Foundation post earns its keep; the Philosophy post tells you what to do with the keep you’ve earned.
If any of this struck a nerve — the seventeen-year version of you, the move you keep almost making, the number you’re chasing without quite knowing why — then you’re exactly who I’m writing for.
Let's embark together. Let's enrich your life, not just your account.
Reply and tell me: what’s the one change you keep circling but haven’t made? I read everything.
— Ashleigh