I'm the Last Person Who Should Have Needed a Financial Advisor

And I needed one anyway.

My father is a retired business school professor. I grew up around people who understood finance, law, medicine, and institutions, and I got an MBA in finance myself and spent years in corporate finance, consulting, and executive leadership. My family even had a complimentary advisor through one of the country's largest and most established retirement institutions — the kind of name you'd recognize — connected to my father's long career at the University of Michigan.

So why would I need to hire anyone? I could read a prospectus, build a projection, look up a tax question. The technical stuff was never the hard part. And whenever the private banking invitations showed up in my mailbox — thick cardstock, polished branding, "personalized" private client experience — I had the same reaction: what is a ~1% fee actually going to buy me that I can't do myself?

For most of my life I couldn't come up with a good answer. Turns out I was asking the wrong question. The real one isn't whether you're smart enough to manage your own money — it's who is actually responsible for catching what you don't know to look for.

We were failed anyway

Recently I was reviewing my parents' old tax returns — the kind of review I now do for the families I work with — and I found a tax bill they never should have paid.

When you sell an investment, you're generally taxed on the gain: what you sold it for, minus what you originally paid. That second number, your cost basis, is the whole game. Somewhere over the years, the record of what my parents had paid for one investment had simply gone missing, so when part of it was sold, almost the entire sale got treated as profit. It wasn't. They overpaid by tens of thousands of dollars. (The full story deserves its own post: the six figures of missing basis, how I rebuilt the trail going back twenty-six years, and how we clawed most of it back.)

But the part that still gets me is this. Fifty years with the same institution. An assigned advisor the whole time. A father who taught this stuff for a living. And nobody caught it — not once

Financial knowledge isn't the same as financial oversight

That's what changed how I think about advice. My father had knowledge, I had knowledge, his whole network had knowledge — plenty of people around us could have spotted the issue. But it wasn't anyone's job. A network answers the questions you bring to it, if you know the right one to ask. The expensive mistakes are different: they sit quietly in old tax returns, old statements, old beneficiary forms, old account registrations, old assumptions. And when it's nobody's defined responsibility to go looking for them, "someone should have noticed" becomes "no one did."

That was the real failure in my family. Not intelligence, not access, not credentials — accountability. Being able to do something isn't the same as having the time and structure to do it well, year after year. That's especially true for the people I work with most — physicians, executives, business owners — whose incomes and lives are complex precisely when their time is scarcest, juggling a career, a family, aging parents, taxes, estate documents, insurance, and everything else that comes with a real financial life. The expensive misses weren't failures of intelligence. They were failures of attention — and attention is the one thing no credential substitutes for.

The default isn't always responsibility

Part of what makes this hard is that the titles tell you almost nothing. "Financial Advisor," "Wealth Manager," "Financial Planner" — most people hear those words and assume someone is watching the whole picture. Often they're not. Sometimes the title means a good person working inside a structure that still rewards asset gathering, product sales, and keeping money in-house.

That doesn't make every large firm bad. But structure matters. When advice lives inside a company that also builds the products, controls the platform, and benefits when your assets stay there, the incentives lean a certain way — quietly, legally, often invisibly to the client. That's why the default wins: not because families weighed the options and chose it, but because it's already there. One click, one envelope, one "complimentary consultation" away. And once you're inside the system, it's easy to assume someone is watching. Sometimes someone is. Sometimes nobody really is.

One question

If you're thinking about getting help — or you already have it and aren't sure it's the right kind — ask this:

"Are you a fiduciary, on every account, all the time — and will you put that in writing?"

"Fiduciary" means the advisor is legally required to put your interests ahead of their own. It sounds like that should be the baseline for anyone handling your money. It isn't. And the important part isn't whether someone can use the word — it's whether the duty applies to every account, every recommendation, every time.

Here's the catch I learned firsthand. Years ago, an advisor at a large financial services & insurance company sold me life and disability coverage and told me plainly he'd put my needs first. I believed he meant it. What I also knew: he was paid by commission, and the products that paid him most weren't always the cheapest ones for me. That's the loophole. An advisor can genuinely act in your best interest on some of your accounts while still being paid to sell you products on others. The fiduciary promise and the sales commission can live side by side. So the real follow-up question is simpler: how are you paid, and does it change depending on what you recommend?

It's the question I had to learn to ask. It's also the standard I hold myself to now: fee-only, no products to sell, accountable for the full picture. A firm built that way should be able to answer clearly. If you get "depends on the product," "in most cases," "for advisory accounts," or just a long pause — that tells you something.

The lesson

I had about every advantage a person could have, and I still learned the hard way that "reputable" and "actually responsible for me" are not the same thing. Sometimes they line up. Sometimes they don't. In my family's case, the gap cost real money for years before anyone noticed.

So the question isn't "am I smart enough to do this myself?" The better question is: who is responsible for catching what I don't know to look for? That's what good advice is supposed to be — not a product, not a pitch, not a glossy invitation, but competence applied with diligence, over time, by someone whose job is to stay responsible after the paperwork is signed.

Next post: the actual story — the six figures of missing cost basis, the tax bill that never should have happened, and how I rebuilt the trail going back twenty-six years.