I founded Money Talks News in 1991. Ever since, I’ve tried to answer every money question readers throw at me — in columns, on TV, in the newsletter, on the podcast. Add it up, and it’s more than 30,000 questions over 35 years.
Here’s what all those questions taught me: The worries barely change.
The tools change — Zelle instead of checkbooks, robo-advisors instead of brokers in bad suits. But the fears underneath stay exactly the same.
I’m a CPA, and I spent about a decade as a Wall Street investment advisor before I quit to give honest advice instead of selling products. So I’ve heard these questions from both sides of the desk.
Here are the seven I get most — and my straight answer to each.
1. When should I claim Social Security?
This one laps the field. It’s the biggest money decision most people ever make, and most folks blow it by grabbing benefits at 62 out of fear the money won’t be there.
Claim at 62 and — if your full retirement age is 67 — you’ll take a 30% cut for life. Wait until 70 and the Social Security Administration pays you 124% of your full benefit instead. That’s roughly 77% more than the age-62 check, and it never goes away.
There’s no single right answer. It depends on your health, your savings, and your spouse. I broke down exactly how I’d weigh it in my honest take on when to claim.
2. Should I buy an annuity?
Some annuities are fine — an immediate annuity can work like a DIY pension. The problem is the ones sold hardest tend to pay the salesperson the fattest commission, not the ones that fit you.
Here’s my rule: If you can’t explain in one sentence how a thing makes money, don’t buy it. And watch the fees — they’re often hidden, but they can be monsters.
I wrote a full breakdown of how annuities actually work — and when they’re worth it.
3. Should I pay off my mortgage before I retire?
Depends entirely on your rate. Under 4%, the math says keep it and invest the difference. Over 6%, killing it is close to a guaranteed return you can’t beat anywhere else.
But never drain a 401(k) or IRA to do it — the tax hit can push you into a higher bracket.
And if the debt keeps you up at 3 a.m., pay it off and ignore the spreadsheet. I ran the full math on carrying a mortgage into retirement here.
4. Do I really need a financial advisor?
Some people do. Some don’t. But here’s the part nobody tells you: Most people who hire an advisor aren’t buying better returns. They’re buying peace of mind and someone to stop them from panic-selling.
That’s a real service — if you’re paying for advice, not for a sales pitch.
The catch is knowing which one you’ve got. Here’s what people are really paying for and how to tell the difference.
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Quick aside — most internet financial advice comes from people who weren’t alive during the last recession. I’ve been writing about money for more than 35 years. Want rock-solid advice? Sign up for the free Money Talks Newsletter. Takes 10 seconds. No fluff. No spam.
5. Should I co-sign a loan for someone I love?
When somebody asks you to co-sign, here’s what’s really happening: A professional lender whose entire job is judging risk looked at that person and said no.
Co-signing puts you on the hook for the whole debt. And the Federal Trade Commission warns that the lender doesn’t have to chase the borrower first — they can come straight for you.
I’ve done it anyway, so I get it. If you’re going to, at least protect yourself first.
6. How do I keep from getting scammed?
Fear, urgency, and a trusted name. That’s the whole trick, and it hasn’t changed in 35 years — only the technology has.
The IRS doesn’t call you. Social Security doesn’t call you. Nobody legit demands gift cards or wire transfers on a deadline.
My best defense costs nothing: Pick one trusted person and call them before you move any money. I laid out the seven rules that stop almost every scam.
7. Do I have enough to retire?
The most-asked question of all — I’ve heard it a thousand times, going back to my stockbroker days. And it’s got the least satisfying answer, because it truly depends on you.
Ignore any online calculator that spits out a single magic number. Change one assumption — your return, inflation, how long you live — and the answer swings by hundreds of thousands.
So skip the guesswork. I laid out a five-step way to find your own number in about 30 minutes. That beats any calculator.
The bottom line
Thirty thousand questions in, here’s the thread running through all of them: The financial world is built to make simple things feel complicated, because confusion is where the fees hide.
None of this is as hard as it looks. It just has a lot of people invested in making you think it is.
If you’ve got questions of your own, subscribe to the Money Talks Newsletter and let’s work through all this together.
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