The Unspoken Cost of Getting Money “Right”
Episode 731 of Earn & Invest: Ten Things I Messed Up With Money
A few decades ago, I sat across from a financial advisor and did something that felt responsible…almost like a rite of passage into adulthood. I handed everything over. Investments, decisions, control. It wasn’t impulsive; it was deliberate, even thoughtful. Because somewhere along the way, I had absorbed a belief that felt both humble and limiting at the same time: I’m not the kind of person who should be doing this myself.
I’m Jordan Grumet—most people know me as Doc G from the Earn & Invest—and in this episode, I found myself doing something a little uncomfortable.
Instead of talking about what I got right, I started naming the places where I got it wrong.
The mistake that looked like love
In my twenties, I bought a whole life insurance policy from my brother. At the time, it didn’t feel like a financial decision so much as a relational one. Saying yes meant supporting someone close to me. It meant trust, alignment, maybe even a sense of doing the “right” thing.
Years later, I realized it wasn’t a good use of my money and cashed it out at a loss.
It would be easy to call this a product mistake and move on. But that’s not really what it was. Many of my financial decisions, maybe yours too, have been shaped less by spreadsheets and more by relationships, identity, and the quiet pressure to be a certain kind of person.
The career that paid more and cost more
There was also a fork in the road early in my medical career. One path led toward hospice work—deeply meaningful, emotionally rich, aligned with the kind of impact I would later come to value. The other path offered a more traditional trajectory: general internal medicine, with higher income and clearer prestige.
I chose the latter.
And for a while, it worked. Until it didn’t.
Burnout didn’t arrive all at once. It crept in slowly, almost invisibly, until the thing I had optimized for: income, stability, approval, started to feel misaligned with the life I was actually living. In the end, that choice shortened my career. Ironically, the “safer” path may have been the one that carried more long-term risk.
I used to think purpose was something you pursued after you got everything else in order. Now I wonder if it’s the thing that holds everything else together.
The comfort of familiar investments
At one point, I followed a piece of advice that sounded too reasonable to question: invest in what you know. When my grandmother moved into an assisted living facility, I decided to buy stock in the company.
It felt intuitive. Grounded. Personal.
And then… nothing happened.
I held that investment for over a decade without meaningful returns. Meanwhile, the broader market—the boring, impersonal index funds—kept quietly compounding in the background.
There’s something comforting about familiarity. It makes us feel informed, even when we’re not. But I’ve learned that familiarity isn’t the same as advantage. Sometimes it’s just a more comfortable way to stand still.
When frugality becomes identity
In my younger years, I prided myself on being careful with money. Disciplined. Intentional. And those traits served me well, especially when it came to the big decisions.
But then something started to shift.
I found myself stressing over small purchases, like whether to buy my wife a pair of shoes. Not because we couldn’t afford it, but because spending, even modest spending, started to feel wrong.
Frugality had quietly moved from being a tool to being part of my identity. And once that happens, it’s hard to see clearly. You start doing everything “right,” but living in a way that feels tighter than it needs to be.
The beliefs I never questioned
For years, I believed that a 4% return on investments was solid. Not as a withdrawal rule, just as a general expectation.
I didn’t analyze it. I didn’t question it. I just accepted it and moved on.
Looking back, that small, unexamined belief shaped my expectations more than I realized. It kept me aiming lower than I needed to for years.
We spend a lot of time worrying about complex strategies, but it’s often the simple assumptions, the ones we never revisit, that quietly steer the ship.
Avoidance, disguised as outsourcing
At some point, I handed off my investments entirely. Then my taxes, too.
On the surface, it looked like maturity. Delegation. Efficiency.
But underneath, there was something else going on. I didn’t believe I was smart enough to manage these things myself. So I opted out.
What I didn’t expect was the cost of that disengagement. Lower returns were part of it. But more than that, there was a lingering anxiety that came from not really understanding what was happening with my own money.
When you don’t understand something, you can’t fully trust it. And when you can’t trust it, you carry that uncertainty with you.
When spending becomes another obligation
Later, I came across the philosophy behind Die with Zero. A compelling argument for spending more freely and intentionally during your lifetime.
At first, it felt like a release. A correction to years of saving and restraint.
But over time, it started to feel like a different kind of pressure.
Instead of worrying that I wasn’t saving enough, I began to feel like I wasn’t spending well enough. Lavish trips, carefully planned experiences—none of them reliably created the sense of fulfillment I expected.
It turns out you can’t force meaning. And trying to do so can feel just as constraining as holding back.
When the plan meets reality
Eventually, life introduced a variable I hadn’t fully prepared for. My wife retired unexpectedly, and it happened during a downturn in the market.
In that moment, my portfolio—still heavily weighted toward equities—felt far more exposed than it ever had on paper. What worked during accumulation didn’t translate cleanly into decumulation.
It’s one thing to build a plan when everything is hypothetical. It’s another to live through it when the timing shifts and the stakes feel immediate.
The mindset underneath everything
When I look back at these mistakes, what stands out isn’t just the decisions themselves, but the mindset underneath them.
There was a persistent sense of scarcity: a feeling that things could fall apart, that I needed to be careful, that there might not be enough.
That mindset showed up in different ways: worrying about the 4% rule, hesitating over small expenses, stepping away from decisions because I didn’t trust myself.
And then, gradually, something changed.
Not because the math suddenly improved, but because my relationship to uncertainty did. I started to believe that if things went wrong, I could respond. I could earn again, pivot, adjust.
The safety I had been searching for in numbers alone started to feel more internal.
Rethinking what it means to “win”
Toward the end of the episode, a listener—a tax professional—pushed back on something I’ve heard often in financial independence circles: the idea that the goal is to pay as little tax as possible.
Ideally, zero.
His argument was simple. Taxes fund the systems we all rely on—roads, legal structures, public goods. The very framework that makes wealth-building possible.
And the more I thought about it, the more I agreed.
If I’m paying a lot in taxes, it likely means I’m doing very well financially. In that sense, taxes aren’t just something to minimize—they’re a reflection of participation.
It’s not the most popular way to think about it. But it feels honest.
What these mistakes actually cost
None of these decisions ruined my life. Most were recoverable. Some were barely noticeable on their own.
But taken together, they point to something deeper.
The real cost wasn’t the money I lost on an insurance policy or the gains I missed in a single stock. It was the accumulation of small misalignments…years spent optimizing for the wrong things, carrying unnecessary stress, or operating from beliefs I hadn’t fully examined.
And maybe that’s the part that’s hardest to measure.
You can be disciplined, thoughtful, and well-intentioned with money, and still feel slightly out of sync with the life you actually want to live.
If you want to hear how these moments unfolded in real time—the context, the emotion, the thinking behind them—the full episode goes deeper than I can here.
Because this isn’t really a list of mistakes.
It’s a story about how I learned to see them.
This is such a good reminder that getting the money “right” can still leave you misallocated. The spreadsheet may look responsible while the life underneath it is carrying quiet basis risk: identity, fear, relationships, old assumptions, and purpose deferred too long. The real audit is not just whether the numbers worked. It’s whether they served the life they were supposed to fund.