The investment choices that seemed smart a few years ago aren’t always aging well. Market shifts, economic changes, and new information have left many investors questioning their decisions. Here are seven investments that people are wishing they could take back.
Cryptocurrency at Peak Prices
Buying Bitcoin at peak prices or chasing the latest meme coin felt exciting at the time. Now those same investors are sitting on losses they can’t shake off. Crypto remains volatile and unpredictable, which is fine if you got in early. But people who bought during the hype years are still underwater.
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The problem wasn’t crypto itself. The problem was timing and overconfidence. People dumped their emergency funds into digital coins because influencers promised easy money. They ignored basic investment rules like diversification and risk management. Now they’re stuck holding assets worth far less than what they paid. Some are still convinced it’ll bounce back. Others have accepted the loss and moved on to more stable options.
Overpriced Real Estate in Bubble Markets
Real estate always goes up, right? Not exactly. People who bought houses in recent boom years paid inflated prices during bidding war frenzies. They waived inspections, offered over asking price, and stretched their budgets to the limit. Interest rates were low, so the monthly payments seemed manageable.
Then rates jumped dramatically and home values dropped in many markets. Now these homeowners owe more than their houses are worth. They’re trapped because selling means taking a loss. Refinancing doesn’t help because rates are higher now.
The dream home turned into a financial anchor. This isn’t happening everywhere, but bubble markets like Austin, Boise, and Phoenix saw major corrections. People who bought at the peak are feeling the pain, discovering hidden costs of homeownership they never anticipated.
NFTs and Digital Collectibles
Remember when NFTs were going to change everything? People spent thousands or even millions on digital art and collectibles. The hype was real for about six months. Then the market collapsed harder than a house of cards in a windstorm.
Most NFTs are now worthless. The jpeg you bought for thousands can’t find a buyer at a fraction of that price. Trading volume dried up and interest vanished. A few rare pieces from major artists still hold value, but the vast majority became expensive lessons in speculation.
People thought they were investing in the future. They were actually gambling on a trend that burned out fast. The technology might have uses someday, but buying random digital art at inflated prices wasn’t the play.
High-Fee Mutual Funds
Mutual funds with high expense ratios are eating returns alive. People invested in these funds through their 401(k) or financial advisor without checking the fees. They assumed professional management was worth the cost. It usually isn’t.
Index funds that track the market charge minimal fees. Actively managed funds charge significantly more. That difference compounds over decades into massive amounts of lost returns. Study after study shows most active managers don’t beat the market after fees.
You’re paying extra for worse results. Investors who realize this are moving money to low-cost index funds. The ones still making common investment mistakes continue losing money to fees every single year.
Extended Car Warranties and Gap Insurance Add-Ons
Car dealerships are masters at selling add-ons during the finance process. Extended warranties, gap insurance, paint protection, and fabric sealant all sound reasonable when you’re signing papers. Then you realize you paid thousands for coverage you’ll never use.
Extended warranties rarely pay off. Cars are more reliable now than ever before. The warranty terms have so many exclusions that getting a claim approved is nearly impossible. Gap insurance makes sense in specific situations, but dealers charge triple what insurance companies charge for the same coverage.
Paint protection and fabric sealant are pure profit for the dealership. You can buy better products cheaply and apply them yourself. People who financed these add-ons are now making payments on overpriced insurance while dealing with rising car costs that keep climbing.
Timeshares and Vacation Clubs
Timeshares represent one of the worst financial decisions you can make. The sales pitch sounds amazing. Lock in vacation costs forever. Build family memories in beautiful locations. Enjoy luxury accommodations at member prices. Then reality hits and you realize you bought a liability disguised as an asset.
Maintenance fees climb every year. Booking the dates you want is impossible. The property gets older and shabbier but your fees keep rising. Trying to sell is a nightmare because the resale market is flooded with desperate owners. Some people pay companies thousands of dollars just to get out of their timeshare contracts.
You can rent nicer accommodations through regular booking sites for less money and zero commitment. Timeshare owners in 2025 are searching for exit strategies and warning everyone they know to stay away.
Speculative Penny Stocks
Penny stocks promise massive returns for small investments. Put in a few hundred and turn it into tens of thousands. That’s the dream anyway. The reality is most penny stocks are garbage companies with no real business model. They exist to separate hopeful investors from their money.
These stocks trade for pennies because they’re nearly worthless. They’re not undiscovered gems waiting to explode. They’re failing businesses or outright scams. People who bought penny stocks based on Reddit tips or email newsletters are sitting on worthless shares.
The liquidity is terrible so you can’t even sell without tanking the price. Some investors lost everything chasing the next big score. Those who learn to avoid common investing mistakes stick with regular stocks from established companies that actually make money over time.
Learning From Mistakes
Bad investments happen to everyone. The key is recognizing mistakes early and adjusting course. Holding onto losing investments because you don’t want to admit failure just makes things worse. Cut your losses when needed and redirect money to better opportunities.
These regrettable investments share common threads. They were driven by hype, emotion, or pressure rather than solid research. People ignored warning signs because they wanted the investment to work. They prioritized quick gains over long-term stability. Understanding what went wrong helps you avoid similar mistakes.
The best investment strategy is usually the boring one. Low-cost index funds, diversified portfolios, and patient long-term holding beat speculation almost every time. You won’t get rich quick, but you will build wealth steadily. That’s worth more than any get-rich-quick scheme promising impossible returns. Building strong financial habits matters more than chasing the next hot investment trend.
This article first appeared on Cents + Purpose.