Most people who hand out money advice never circle back to admit they were wrong. That’s how you get 35 years of confident opinions and zero accountability.
Let me go the other direction.
I’ve been writing about personal finance since 1991. I became a CPA in 1981 and spent the decade after that as a Wall Street investment advisor. Two Emmys along the way.
I’ve also been flat wrong more times than I’d like to count.
Here are nine of the worst pieces of advice I handed out that was either incorrect or so oversimplified. Some I figured out the hard way.
1. I thought you should never buy individual stocks
When I wrote my first book, “Life or Debt,” back in 2001, I told readers that since they can’t outperform the market, they should just invest in broad-based index funds, like an S&P 500 fund.
I wasn’t technically wrong. S&P Dow Jones Indices found that 79% of actively managed large-cap U.S. stock funds underperformed the S&P 500 in 2025. Stretch the window to 20 years and roughly nine out of 10 domestic funds trailed their benchmarks.
Those are facts. But here’s something that I’ve learned over the years. While stock mutual funds have trouble beating an index, it’s still possible to make money — a lot of it — by buying quality individual stocks and holding onto them for long periods of time.
Today my advice is to put 80% to 90% of your long-term savings into index funds, but if you’re willing to do a little work, try a stock or two as well.
I haven’t been right on every stock I’ve owned, of course, but I’ve made well into seven figures by investing in companies like Apple, Google, Nvidia, Meta and Microsoft. That’s not an endorsement of those companies. I bought them all many years ago.
But if you can see a trend coming, are willing to do some research, have patience and happen to be at the right place at the right time, individual stocks can change your life.
2. I thought getting rich was mostly about spending less
For years my advice boiled down to this: Track everything, cut everything, and wealth will follow.
It’s not wrong. It’s incomplete, and the incompleteness matters.
Here’s the trouble. There’s a floor on how much you can cut. Rent has a number. Insurance has a number. Groceries have a number. Squeeze hard enough and you hit bone.
But there’s no ceiling on what you can earn.
The reader who spent a weekend learning a skill that added $15,000 to their salary beats the reader who spent five years clipping coupons. I wrote far too many columns for the second person and not nearly enough for the first.
The reason so many personal finance writers talk about saving money is because the steps to take are well-defined and the same for everybody. Making money is more personal. Not the same for everyone, thus more difficult to fit into a neat list.
Nonetheless, cutting costs is defense. Nobody wins on defense alone.
3. I told people renting was throwing money away
I still believe that owning a home is a worthwhile endeavor. It sounds obviously true, and I haven’t rented a home since I was in my 20s.
But I’ve written as if it’s the right move for everyone. It isn’t.
Rent buys you shelter. A mortgage buys you shelter plus property taxes, insurance, maintenance, closing costs and a mountain of front-loaded fees. Run the numbers in a pricey market, and renting sometimes wins outright.
Owning a home is still a perfectly good goal, if you’re staying put and if you’re in a city that’s growing. But it’s not a character test. There are situations, especially now that housing has gotten so expensive, when renting could be the better bet.
4. I said to always claim Social Security at 70
The logic sounded airtight. The longer you put off taking Social Security, the more you’ll get every month. Wait past your full retirement age and Social Security adds roughly 8% a year to your benefit, up to age 70, according to the Social Security Administration. That’s a guaranteed, inflation-adjusted raise for the rest of your life.
No brainer.
But over the years I’ve come to realize that what’s right for some may not be right for all. I waited till 70 to take Social Security, but I work at a desk in my house, not on a factory floor where I’m counting the minutes till the whistle blows.
Claiming early can be the right move for some people. If you need the income, hate your job, your health is shaky or your family isn’t known for its longevity, take it early. Sure, the math may suggest you wait. But the math isn’t the only consideration.
5. I called bonds the safe part of your portfolio
Every portfolio conversation I had for three decades included the same tidy line. Stocks for growth, bonds for safety.
Then 2022 arrived.
The Bloomberg U.S. Aggregate Bond Index — the standard yardstick for the American bond market — fell about 13% that year. Worst calendar year in the index’s history, which reaches back to the 1970s.
Bonds are typically less volatile than stocks, which are a completely different thing.
When rates climb fast, bond prices drop hard. I understood that mechanically. I just never said it plainly enough to the people who needed to hear it.
Quick gut-check — if your money advice is coming from random online influencers, you’re playing a dangerous game. I’ve been a CPA since 1981 and writing about money since before the internet existed. Sign up for the free Money Talks Newsletter and get expert advice that’s been tested by time.
6. I went to cash when I got scared
I traded through many bad markets: 1987, the dot-com collapse, 2008 and a few lesser panics. And what I did for the first few of them was nothing. I stood like a deer in the headlights, afraid to make a move.
I also got out of stocks when the market started looking shaky. Going to cash feels smart in the moment. It feels like seizing control.
The problem is getting back in. Nobody rings a bell at the bottom. A Wells Fargo Investment Institute analysis found that nine of the S&P 500’s 10 best trading days over the past 30 years landed during recessions.
So the fear that drives you out is the same fear that keeps you out while the recovery runs without you. I laid out the rest of that math in why market timing wrecks retirements.
After standing on the sidelines during multiple recessions, I finally learned my lesson. In 2009, when everyone was selling, I started buying. I still own many of those stocks today, and have done very well indeed.
Today, I think the market is too high and my instinct is to sell. But instead of adjusting my portfolio, I’m adjusting my expectations.
7. I thought everybody needed a written budget
I pushed budgets hard. Categories, spreadsheets, receipts in envelopes, the whole apparatus.
There’s nothing wrong with that, and it’s generally a good idea to know exactly where your money’s going. The only problem? Most people won’t do it. That’s not a character defect. It’s just a fact.
What I do these days is track my net worth: what I own, less what I owe. If I’m richer at the end of the month than when it began, I’m done. I don’t need to track individual expenses.
Exception: If you’re in financial trouble, you should still track your expenses to find out where the problem is and what you can do about it.
But if you’re not in trouble, just track your net worth and keep paying yourself first. Money moves into savings and investments the day it arrives, before anyone can touch it. You spend what’s left and track nothing.
Same result. No willpower required.
8. I said a degree was always worth the debt
For most of my career, I treated college as an automatic yes. Borrow whatever it takes. It pays for itself.
But when I went to college, my out-of-state tuition was $600 a semester. My middle-class parents had no problem putting me through school.
But that was then. Americans now owe close to $1.9 trillion in student loans, according to the Federal Reserve. The Fed’s own household survey found that about 15% of borrowers with payments due recently paid less than they owed or paid nothing at all. People are now taking student loan debt into retirement.
The cost of college in this country is a disgrace, and the old advice no longer applies.
Knowledge for its own sake is still laudable, and a degree can still be the best investment you’ll ever make. But not going to college doesn’t make you a failure. As costs have soared, now it depends on what you study, where you study it and what you borrow to get there.
“Always” is no longer the right word.
9. I thought money was a math problem
I’m a CPA. I came up believing that if you showed people the correct math, they’d do the correct thing. Compound interest doesn’t lie. Just look at the chart.
The thing is, nobody does the right thing because of a chart.
People buy cars to feel successful. People stop opening statements because they’re ashamed. People hold losing stocks because selling means admitting a mistake. People are embarrassed to get help with their debt.
Taking the time to understand why you do the things you do and learning how money plays into leading the life you want to lead aren’t as easy to write about, but it’s important.
It took me 35 years to understand that money is a behavior problem wearing a math costume.
What all nine have in common
Read that list back and one thing jumps out. Nearly every mistake came from being too certain. Too black and white. Too right and wrong.
Certainty sells. It makes for a punchy TV segment and a shareable headline. But it also makes advice brittle, because the world keeps changing and certainty doesn’t bend.
So if you’re taking money advice from anybody — me included — remember that even the most obvious math ignores the fact that we’re not formulas. We’re people.
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