I didn’t build wealth because I had a plan.
I built it because I followed the rules — long before I understood what the rules were actually doing.
Growing up, money lived in envelopes. Real ones. Handwritten labels. Groceries. Mortgage. Vacation. Back to school. Christmas. Each envelope had a purpose and a boundary. You didn’t borrow from Christmas to buy groceries unless something had gone very wrong. The labels weren’t suggestions — they were constraints. And on the front of the envelope, you kept track: what went in, what came out, and what was left. A tiny ledger that made the rules visible.
At the time, it didn’t feel like learning about money. It felt like order. Like staying inside the lines.
So when I got my first real job and someone explained a 401(k), I didn’t understand compounding or tax deferral or index funds. What I understood was simpler:
If you contribute, your employer will match it.
That sounded like a rule. And it sounded like free money. So I did it.
I stayed at that first job for about ten years. Money went in every paycheck. I didn’t monitor it closely. I didn’t try to time anything. I didn’t even fully understand what the money was doing — mostly because I didn’t know enough to interfere.
When I eventually left and rolled that account into a rollover IRA, it wasn’t a strategic move. It was just the next thing you’re supposed to do if you don’t want to break what’s already working.
Then I went to the next job. Same pattern. Contribute. Take the match. Follow the rule. When I left, that account joined the same rollover IRA too.
At no point did I think I was building wealth. I thought I was avoiding mistakes.
Before podcasts, before dashboards, before AI, I also had financial advisors — the kind many boomer parents have and recommend like it’s a rite of passage. Friendly. Confident. Percentage-based. They handled things for you, which felt like adulthood.
What I didn’t understand then was what that percentage actually did over time.
It wasn’t just a fee. It was a drag on compounding.
When someone takes a cut off the top every year, you don’t just lose that percentage — you lose everything that money could have become. And because compounding works quietly and over long periods, the cost stays mostly invisible. You don’t see what didn’t grow. You don’t see the missing years of growth you paid for in exchange for reassurance.
Later, once I understood how accessible the underlying system actually is — especially through places like Schwab and Vanguard — it became hard to justify paying a perpetual toll just to stand between me and my own money.
The real shift for me came when I stopped thinking in envelopes altogether.
For a long time, even as my accounts grew, my mindset stayed labeled: this money is for this, that money is for that. Everything felt siloed and fragile. I was zoomed in so tight that every decision felt heavier than it needed to be.
Eventually, I pulled everything together — retirement accounts, brokerage, cash, loans — not to judge it, but to see it as one whole picture.
That’s when something clicked.
This wasn’t a set of labeled piles anymore. It was a system.
Money wasn’t static. It moved. Some of it compounded in the market. Some of it reduced future taxes. Some of it created flexibility. Some of it stabilized risk. Different roles, same flow.
Once I started thinking that way, decisions became easier — not because they were obvious, but because they were contextual. I wasn’t asking “What is this money for?” anymore. I was asking “What role does this play over time?”
A big part of that shift came from Rich Habits. It’s a personal finance podcast that focuses less on hacks and more on patterns — the repeatable behaviors that tend to show up in people who build stability over decades. For me, the most important thing it taught wasn’t a product or a trick. It was to track net worth consistently — not obsessively, not daily, but enough to see direction instead of noise.
I tried Rocket Money first. It helped, but it didn’t quite stick. Eventually I found Copilot for Money, and that’s when the system became visible. Not just accounts, but relationships — the way cash, debt, investing, and goals interact. It took the “envelope” idea and modernized it into something I could actually use without being trapped by labels.
That same zoomed-out mindset is what made one of the most useful strategies in my life finally make sense: how I use my HSA.
When I was still thinking in envelopes, the HSA felt like “medical money.” You spend it when you need it. End of story. But once I stopped labeling every dollar with a permanent identity, I could see what the HSA actually is: a tax-advantaged investment vehicle with a unique benefit if you can afford to let it sit.
So now, when I have a medical expense, I often pay out of pocket and keep the receipt. Then I reimburse myself later — sometimes much later.
Here’s what that’s doing for me long-term:
- It keeps HSA dollars invested longer, so they have more time to compound inside a tax-advantaged account.
- It gives me optionality: those receipts are effectively a future “tap” I can pull years later if I ever need cash.
- It changes which dollars I’m using over my lifetime — by letting a tax-advantaged bucket grow while using current cash flow today.
That strategy only works if you stop thinking in rigid labeled envelopes and start thinking in timelines and flows. It’s not about deprivation. It’s about letting the system do what it does best: reward time.
Today, I also use AI as part of that system — not as an authority, and not as a replacement for judgment. More like a second set of eyes. A way to sanity-check the model I’ve built from tracking, listening, and learning.
I’ll ask: am I thinking clearly here? am I missing something obvious? does this move fit the long-term flow, or is it just me reacting?
Most of the time, what comes back is the same quiet answer:
This works because you’re letting compounding do its job.
What still surprises me isn’t that any of this works.
It’s how long I followed the rules before I understood why they existed.
Once you zoom out far enough, the financial world starts to look less like a set of separate decisions and more like a system you can actually read. Not perfect. Not fair. But legible. And when it becomes legible, you stop paying unnecessary tolls just to feel reassured.
That clarity — not optimization, not shortcuts — is what changed everything.