I almost bought a boat when I retired. Not because I wanted a boat — I don’t even like being on the water that much. But I’d been working for 35 years, I had some money saved up, and I thought, “I deserve a reward.” My neighbor had a boat. He was always out on it, posting photos. It looked like the kind of thing retired people should have.
So I went to look at boats. A nice one was $80,000. That’s not nothing. But I was thinking about the photos I’d post, the conversations I’d have at the dock, the image of myself as a guy who had a boat. I was almost ready to buy.
Then my wife asked me one question: “How often will we actually use it?” I did the math. Maybe 20 days a year, if we were lucky. That’s $4,000 per use. Plus storage, maintenance, insurance. The total cost over 10 years would be closer to $150,000. For 200 days of actual use.
I didn’t buy the boat. And I’m glad I didn’t. Because that would have been exactly the kind of purchase retirees regret — buying something for the image, not for the actual use.
Here’s what I’ve learned after 20 years of working with retirees: the purchases they regret most aren’t the ones they needed and didn’t buy. They’re the ones they bought for the wrong reasons — to impress someone, to fill a void, to prove they’d “made it.” These purchases almost always cost more than they’re worth, and they almost always lead to regret. The five biggest categories are: upsizing the house, overspending on travel, buying luxury gifts for others, giving too much to adult children, and buying expensive cars. Let me walk you through each one and show you how to avoid the trap.
1. Upsizing your house (the most expensive regret)
This is the number one regret I see. Retirees sell the house they raised their kids in and buy a bigger, fancier house. They think they want more space for when the grandkids visit, or they want a nicer neighborhood, or they just want to “downsize” to something more manageable. But “more manageable” often turns into “more expensive.”
Here’s the math that nobody tells you. A $500,000 house costs about $15,000 a year in property taxes, insurance, maintenance, and utilities. A $300,000 house costs about $9,000. That’s $6,000 a year you’re spending for the “upgrade.” Over 20 years of retirement, that’s $120,000 — plus the higher purchase price. And for what? A guest room you use twice a year? A bigger yard you don’t want to mow?
I’ve seen this play out over and over. People buy the big house, then realize the costs are eating into their retirement savings. They’re house-rich and cash-poor. They can’t afford to travel, or they’re worried about every repair bill. The house that was supposed to be their reward becomes a burden.
The fix: downsize, don’t upsize. Buy something smaller, cheaper, and easier to maintain. Your house is a tool, not a trophy. The less it costs you, the more freedom you have to do what you actually want to do.
| House Price | Annual Costs (Tax, Insurance, Maintenance, Utilities) | 20-Year Total Cost | What You’re Really Paying |
|---|---|---|---|
| $300,000 | $9,000 | $480,000 (including purchase) | Manageable, more cash for other things |
| $500,000 | $15,000 | $800,000 (including purchase) | $320,000 more for the “upgrade” |
2. Overspending on travel (the romantic regret)
Travel is one of the best parts of retirement. You have the time, you have the freedom, and you’ve probably been dreaming about the places you want to see. There’s nothing wrong with spending money on travel — it’s one of the things that makes retirement great. The problem is when you overspend and blow through your savings.
I’ve seen retirees spend $50,000 on a European vacation. Not over 10 years — in one year. They stay in five-star hotels, eat at expensive restaurants, take private tours. It’s amazing while they’re doing it. Then they get home and realize they’ve spent a chunk of their retirement savings on a two-week trip.
Here’s the thing: travel doesn’t have to be expensive to be memorable. I’ve had clients who took amazing trips for $5,000-10,000 — staying in vacation rentals instead of hotels, eating at local places instead of tourist traps, taking public transportation instead of private cars. The experiences were just as good, but they didn’t blow up their budget.
The fix: set a travel budget and stick to it. Decide how much you can afford to spend on travel each year without jeopardizing your financial security. Then find ways to have amazing experiences within that budget. The memories are what matter, not the price tag.
3. Buying luxury gifts for others (the generous regret)
This one surprises people. Retirees often regret spending money on expensive gifts for friends, former colleagues, or even acquaintances. They buy luxury watches, jewelry, or other high-end items to “show appreciation” or “celebrate relationships.” But then they realize they’ve spent thousands of dollars on people who don’t actually care about the gift — they care about the relationship.
I had a client who spent $10,000 on a watch for his former business partner. They’d worked together for 20 years, and he wanted to give him something special. But his partner was fine with a nice dinner and a heartfelt letter. The watch was just… stuff. And my client later realized he’d spent $10,000 on stuff that didn’t matter.
The fix: focus on experiences, not things. Take people out to dinner. Plan a trip together. Write a heartfelt letter. These are the things people remember, and they don’t cost a fortune. Generosity is wonderful, but it doesn’t have to be expensive to be meaningful.
4. Giving too much to adult children (the parental regret)
This is the one that keeps me up at night. Retirees give their adult children money — for a house down payment, to pay off student loans, to start a business, to cover living expenses. They want to help, and that’s natural. But they give so much that they jeopardize their own financial security.
I’ve seen retirees give away $100,000, $200,000, even $500,000 to their kids. They think, “I want them to have an easier life than I did.” That’s a beautiful sentiment. But then they run out of money at age 82 and have to move in with those same kids they were trying to help. Now they’re a burden instead of a blessing.
Here’s the hard truth: your adult children need to learn to stand on their own feet. If you give them everything they need, they never learn to solve their own problems. And if you give away your retirement savings, you’re not helping anyone — you’re just transferring the burden from one generation to the next.
The fix: set a limit on how much you can give without jeopardizing your own financial security. Maybe it’s $10,000 a year, maybe it’s $50,000 total — whatever you can afford without putting yourself at risk. And make it clear that this is a gift, not a loan, and it’s the last one. Your kids will be fine. They’ll figure it out. And you’ll sleep better knowing your retirement is secure.
5. Buying expensive cars (the status regret)
Some retirees buy a luxury car as a reward for a lifetime of hard work. They’ve always wanted a Mercedes, a BMW, a Tesla. They figure they’ve earned it. And maybe they have. But luxury cars are money pits.
Here’s the math. A $70,000 luxury car costs about $5,000 a year in maintenance, $2,500 in insurance, and depreciates by $21,000 in the first year. That’s $28,500 in costs in year one. A $25,000 reliable car costs about $1,500 in maintenance, $1,000 in insurance, and depreciates by $7,500. That’s $10,000 in costs. You’re spending $18,500 more per year for the luxury brand.
Over 10 years, that’s $185,000 you’re spending for the badge. And what do you get? A nicer interior? A smoother ride? Maybe. But at what cost? I’ve seen retirees who bought the luxury car and then couldn’t afford to fill it up with gas.
The fix: buy a reliable, comfortable car that fits your budget. If you want a nice car, buy a nice car — but not a luxury car. There are plenty of non-luxury vehicles that are comfortable, reliable, and status-free. The people who actually matter don’t care what you drive. And the people who do care aren’t worth impressing.
The bigger picture
Here’s what all these regrets have in common: they’re purchases made for the wrong reasons. They’re about image, not utility. They’re about proving something, not enjoying something. They’re about what other people think, not what actually makes you happy.
The best purchases in retirement are the ones that align with your actual values and your actual life. They’re the house that’s easy to maintain, the trips that create memories, the gifts that strengthen relationships, the help that doesn’t jeopardize your security, the car that gets you where you need to go.
If you’re retired or approaching retirement, I’d encourage you to think about what you actually want from this stage of life. Not what you think you’re supposed to want. Not what your friends are doing. Not what the ads are telling you to buy. What do you actually want?
Then build your spending around that. And ignore the rest.
Joshua writes about investing, retirement planning, and building income — the mechanical side of money. He’s not a financial advisor, and this isn’t financial advice. He’s someone who’s been investing for 20 years and made every mistake in the book so you don’t have to. If your situation is complex, talk to a qualified professional.