Financial Experts Share Their Biggest Spending Regrets

These purchases did not reflect wise decision-making, but at least we can learn from them.

From silly impulse purchases to unnecessary splurges, there are many types of transactions people come to regret once it’s time to pay the bills. Fortunately, these experiences can help make us wiser shoppers.

“It’s important to keep in mind that spending regrets typically have lessons associated,” said Bola Sokunbi, founder of Clever Girl Finance. “So it’s important to assess what the lessons are so that you can plan your finances more carefully into the future. We all make money mistakes. What’s most important is that we learn from them.”

Below, Sokunbi and other financial experts share their biggest spending regrets and the lessons they derived from these missteps.

Designer Handbags

“One of my biggest spending regrets is luxury items I barely used, specifically designer handbags in my 20s and other brand clothing. I’m all for buying quality items, but it has to make sense when it comes to cost per wear. I had a collection of items I was barely using that would’ve been a better sense if the money was invested. I learned this in retrospect.

“Personally, I’ve learned to really assess expensive purchases. How would I use the item? Do I need the item? Can the money be put to better use as an investment? These are questions I ask myself and encourage others to ask themselves as well. Eventually, I downsized my collection of luxury bags and invested the money. I lost money on some and made money on others. However, if I had the money invested, I would have made a lot more from appreciation and compounding.” ― Sokunbi

The Newest Macbook

“A spending regret I have is purchasing the latest model of laptop. I ended up using it, and a month down the road, I realized that I would have been just as satisfied with the model before the newest one, which is typically a lot cheaper. For example, the iPhone 14 is about $100 cheaper than the iPhone 15. The MacBook Pro is $900 more than the MacBook Air. This does not mean you always should go with the cheaper option, but it is important to implement a waiting period. For larger purchases, I recommend a month. This gives you time to shop around for the best price, but also to compare models. Is the new feature worth the cost to you, or will you even notice a difference? I bought the MacBook Pro instead of the MacBook Air a few years back when my old laptop died and realized that for the purposes I use a laptop, there was really no difference other than the touch bar at the top ― and that excitement wore off quickly!” ― Kendall Meade, certified financial planner at SoFi

A Big Wedding

“My biggest spending regret is spending over $50,000 on a wedding that I didn’t want and only had to placate my Latino parents as their eldest daughter. They wanted me to have a fairytale wedding, so they ended up using $15,000 from their retirement account to help me pay for my wedding, while I covered the rest. I’m now divorced, so there’s that. It was definitely a waste of money, and if I could do it all over again, I would have done a much smaller thing (or better yet to be honest, not gotten married at all).

“Just because society has normalized spending extravagantly on things like weddings, buying a house, or a new car, that doesn’t mean that you have to. Learn how to value-based spending, i.e. think about what really matters to you and spend your money accordingly, regardless of what ‘the norm’ is.” ― Jannese Torres, creator and host of the “Yo Quiero Dinero” personal finance podcast

A Whole Life Insurance Plan

“I bought a whole life insurance plan that I truly regret. I was 24 and had no clue about insurance and investing. I lost $17k once I actually looked at the numbers and closed the account. One of the biggest lessons is don’t rush to purchase anything, especially financial products that you are not knowledgable about.

“In a social media world full of stories of overnight wealth and success, it can be tempting to throw your money at things that you think will get you there. I think you can regret not spending money on things as well. For money hoarders, this can especially be true. They miss out on opportunities to experience things in life and with others because of their inability to spend.” ― Kara Stevens, founder of The Frugal Feminista and author of “Heal Your Relationship with Money”

Bad Investment Tips

“I’m embarrassed to say that on several occasions, I fell victim to watercooler advice. That is advice that is anecdotal and more rumor-based than knowledge-based. I have spent hard-earned money on speculative stock tips and have lost money more than once. It can happen to anyone. The old expression, ‘If it sounds too good to be true, it probably is,’ is alive and well when it comes to listening to the wrong advice from unqualified sources.

“Another example of a personal blunder was a significant loss I experienced with a condo conversion project that was a miserable failure. A form of greed seems to creep into your normal thought process, and one gets perhaps a little lazy. It’s even worse when you know better and do it anyway. One thing I’ve learned is that nothing comes easy or is certain. If someone is telling you that you can earn money quickly and easily, even if it’s from a close family member or friend, it’s usually a red flag.” ― Lamar Brabham, CEO and founder of Noel Taylor Agency

A timeshare might seem like a good deal, but consider whether you will realistically use it enough to justify the cost.
JOHN COLETTI VIA GETTY IMAGES/A timeshare might seem like a good deal, but consider whether you will realistically use it enough to justify the cost.

A Timeshare

“One of my biggest spending regrets is purchasing a timeshare. It was a hasty decision that comes with an annual fee that does nothing but go up in price every year. Prior to purchasing the timeshare, I should’ve understood it was likely something I wasn’t going to even use every year. Before purchasing something with a contract or annual fee, you should list pros and cons. You should also determine whether that annual fee increases each and every year, and if so, whether or not the increases fit into your budget.” ― Dawn-Marie Joseph, founder of Estate Planning & Preservation

New Credit Cards

“Back in the early ’90s when I was a freshman at The University of Texas, credit card companies would line up near campus giving away school T-shirts if you signed up for a credit card. Before I knew it, I had three different cards maxed out while still a full-time student with no job. The funny thing is I couldn’t begin to tell you what I purchased. I just know that I accumulated over $10,000 in credit card debt. I remember putting the cards in a Ziploc bag, filling it with water, and freezing it. I figured if I really had an emergency, I’d have to work hard to defrost those cards. It took me over a year working a part-time job during my last two years of college to pay off those cards. The biggest lesson I learned was to use credit wisely and sparingly. I learned that there is constructive debt (like your home) and destructive debt (like those frivolous credit card expenses).” ― Cimalie Zoy, director of financial planning at Edelman Financial Engines

Personal Loans

“My biggest spending regret was helping a family member financially when I wasn’t in a position to. I think it’s important to be able to step up for your loved ones when they need help, but it shouldn’t be to your own detriment. In this circumstance, I was helping the person service debts, debts that the person really needed to discharge in bankruptcy. They did not want to file for bankruptcy, so I helped them until they realized they had to do it. Since becoming a financial planner, I now have a deep understanding of how these things work. Because of this, I am better able to advise family members on how to handle such a situation. I also keep a portion of my savings earmarked for family emergencies now, that way I have a reserve set aside for these very circumstances ― and I advise my clients to do the same.” ― Samantha Gorelick, managing financial planner at Brunch & Budget

“My biggest spending regret was loaning an ex-boyfriend thousands of dollars under the impression that I would be made whole once certain ‘life circumstances’ righted themselves. Needless to say, I never saw that money again, and they are still an ex. I now only loan money I’m comfortable giving away, so it was an expensive, but useful, lesson! I think when you start mixing money and people, things can get very emotional very quickly. In my case, I was a single mom at the time and ended up feeling a lot of resentment that my ex would take advantage of me and deprive my kids of financial resources. But it was MY decision to loan the money in the first place, so I own that mistake.” ― Jessica Medina, lawyer turned accredited financial counselor

A Nice Car

“My biggest spending regret was my first car. Instead of following my parent’s advice and getting a car I could buy with cash outright, I decided I needed a newer car. One Saturday afternoon, I went to the car dealership and walked out with a certified pre-owned Toyota Camry. The interest rate was 22% and the monthly payment $535 dollars. If you add insurance for a new driver and other expenses of owning a car, I was paying $800 dollars a month for this car. This was half of my monthly income. Did I mention I was responsible for some of my college tuition and books/fees? Why do I regret it? One, I lived in New Jersey in an area where public transportation was easily available, so I really did not need a car. Two, I paid absolutely zero attention to the interest rate. Three, I was absolutely overextended when it comes to monthly cost of the car.” ― Rose Niang, director of financial planning at Edelman Financial Engines

“I was always a little embarrassed to be the one driving the 25-year-old car, even if it ran great and did its job. When I was older and more established financially, I decided to buy myself a fancy brand new car. Wow, was that a mistake! I worried about the car endlessly — would it get scratched, would someone run into it in a parking lot, was it losing value? Ultimately, I only kept that car for a few years, and my next car was a happy medium ― a newer model used car. And that has been my go-to from that point on — a slightly used car that is in good shape and that I can keep for 8-10 years! I recognize now that I don’t care much about fancy cars, or even just having a new car, as I’d rather spend my money on things that matter more to me, like trips and clothes.” ― Isabel Barrow, director of financial planning at Edelman Financial Engines

Impulse Purchases

“I’d like to have one large item to say I regret spending money on, but in reality, I’d say my biggest spending regret is on all the impulse purchases I’ve made over the years, from clothing deals that seemed too good to pass up and ended up sitting in my closet with the tags still on them (and, nonreturnable) to extra groceries I picked up without a specific meal plan in mind that ultimately ended up in the trash. I literally cringe at the thought of this wasted money! While individually it may not amount to much, collectively this could be a lot of money that could’ve gone towards an income-producing asset. The biggest thing I’ve learned from my spending regrets is to identify my spending triggers and come up with a plan to avoid them in future.” ― Andrea Woroch, money and budgeting expert

Responses have been edited and condensed for clarity.

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