What’s a time you ignored your gut — and paid for it?
View all responses
I’ve generally been pretty good about recognizing bad ideas. When something doesn’t feel right, I usually know it. My problem has been recognizing bad ideas that have been packaged to look like good ones. And over the years, I’ve paid for that. Sometimes quite literally.
When I graduated from high school, my stepfather recommended that I attend Manatee Junior College rather than going straight to Stetson University. He thought I needed a little more time to prepare myself academically before tackling a four-year university. I thought I was ready. After all, I’d gotten into Stetson, hadn’t I?
Turns out, he knew what he was talking about. I failed out of Stetson, and that failure ultimately led me into the Air Force. In hindsight, that wasn’t necessarily the worst thing that could have happened. The Air Force gave me experiences and opportunities that helped shape the rest of my life. But my stepfather had given me good advice, and I hadn’t listened.
I’ve also made some questionable investment decisions. Years ago, I moved money into a EuroPacific mutual fund that I thought I’d researched pretty thoroughly. The following year, it dropped something like 15 percent, perhaps more. Meanwhile, the investment I’d abandoned increased by more than 10 percent. That’s a pretty painful difference, particularly when you’re watching your money go in the wrong direction and realizing that you made the decision yourself.
But if we’re going to talk about ignoring warning signs and paying for it, nothing quite compares to my adventures in timeshare ownership. Yes, timeshares. Plural. And before you say anything, I already know.
Our first timeshare was at Holiday Inn Resorts’ Orange Lake property in Orlando. We made the plunge, and while I’m not entirely convinced it was the soundest financial decision we’ve ever made, I can’t complain too much. It’s a nice property, we’ve used it, and we’ve enjoyed our stays there. So I’m not going to pretend that every timeshare purchase is automatically a disaster.
The disaster came when we decided to buy a second one. We were visiting Hilton Head, South Carolina, and wound up listening to a presentation at Coral Sands. The property was nicer and closer to home, and the sales staff had what sounded like a terrific proposition. They would arrange to market our existing timeshare at Orange Lake, sell it, and use the proceeds to help pay for our new one. What a deal!
We could essentially trade up from one timeshare to another. We weren’t looking to own two timeshares, and the prospect of paying for two of them certainly didn’t appeal to us. But the sales pitch made it sound as though that wasn’t going to be a problem. The old property would be sold, and the money would help cover the new one.
I’m not sure anyone in the history of God’s green Earth has ever successfully pulled off the timeshare version of robbing Peter to pay Paul. But the salesman made it sound perfectly reasonable, and we bought it. Literally.
The second timeshare was supposed to cost $14,500. We signed the paperwork, confident that the sale of the first one would help make everything work. There was just one little problem: We didn’t read the contract closely enough.
As it turned out, there was no guarantee that our original timeshare would actually sell. The arrangement involved marketing the property, not ensuring that someone would buy it. That’s an enormous distinction, and one we failed to appreciate before signing on the dotted line.
The company engaged to market our Orange Lake timeshare eventually went out of business. The property hadn’t sold, and we were informed that we’d signed the contract for Coral Sands and were responsible for paying for it. No apology. No expression of regret. Just the contract we’d signed.
And the salesman? The fellow who had assured me that he’d be my guy for the first year of ownership, the person I could contact if I had any problems? I think he returned one telephone call. After that, nothing. I called. He didn’t call back. So much for having someone looking out for us.
Now, I understand that a signed contract is a signed contract. We should have read every word, asked more questions, and insisted that any guarantee we believed we were receiving be included in writing. That’s on us. There’s no getting around it.
But I also believe that when someone makes a representation during a sales presentation, particularly one that plays such an important role in convincing someone to make a substantial purchase, that representation ought to mean something. In our experience, it didn’t.
And the financial consequences have been considerable. By my estimate, I’ve paid at least $27,000 for a timeshare with an original purchase price of $14,500. That’s roughly $225 a month for at least 10 years. And that doesn’t include the maintenance fees I still owe.
Following my divorce, I fell behind on those maintenance fees. I continued making the monthly mortgage payments, and the mortgage is now paid off. But I still owe maintenance fees, which means I’ve never actually stayed at Coral Sands. Not once. I’ve paid off a timeshare that entitles me to one week every three years, and I’ve never spent a single night there.
Meanwhile, I still own the original timeshare in Orlando. The one that was supposedly going to be sold to help pay for the second one. Some upgrade, huh?
I don’t hate people. I really don’t. But I have a very strong opinion about the way that transaction was handled, and it isn’t a favorable one. I felt that we were sold on a promise that disappeared when it mattered most. The salesman who offered his personal assistance vanished, and we were left with a financial obligation we never intended to take on alongside the first one.
And here’s the part that makes this particularly frustrating: I’m normally cautious about major financial decisions. I don’t particularly enjoy taking big financial leaps, and when something strikes me as a bad idea, I usually have a pretty good instinct for recognizing it.
But this didn’t feel like a bad idea during the presentation. It felt like an opportunity. We already owned something of value, and we were being offered a way to turn it into something better. The sales staff made the process sound straightforward, and we accepted their assurances. My instincts didn’t warn me loudly enough because I thought the biggest concern had already been addressed. It hadn’t.
I’ve learned that there’s a difference between trusting your gut and trusting someone else’s sales pitch. And I’ve learned that a promise made across a desk is worth considerably less than a promise written into a legally binding contract.
I still think instincts are valuable. They’ve served me pretty well over the years, and I usually pay attention when something doesn’t seem right. But I’ve become much more skeptical of opportunities that sound too good to be true, particularly when they involve substantial amounts of money and someone who’s being paid to convince me to part with it.
As for Coral Sands, I own my allotted week. The mortgage is paid off. The maintenance fees remain, and I’ve never been able to enjoy the property. I suppose I could call that an expensive education. At least at Stetson, I actually got to attend classes.
And after all these years, my opinion of that second timeshare remains pretty simple: Worthless. Just like their word.
Enjoyed this? Subscribe and get future reflections, bourbon notes, and assorted nonsense delivered straight to your inbox.
Copyright © 2026 Doug DeBolt.
