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Moneywise staff confesses worst money mistakes — from ignoring subscriptions to sacrificing first home 'must-haves'

AnnaMarie Houlis

Sun, August 16, 2026 at 6:00 PM GMT+3 10 min read

Andrew Aitchison/Getty Images

Even those of us spending our days writing about personal finance and how the rich spend their money aren't immune to making money mistakes. From buying the wrong home at the wrong time to racking up credit card debt, financial missteps can happen to anyone.

That's why we asked Moneywise editors and reporters to share the biggest financial mistakes they've ever made — and the lessons they learned from them. Our candid stories prove that even expensive errors can become valuable learning experiences. Bonus: They may help our readers avoid making the same mistakes.

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1. Ignoring recurring subscriptions

One of the most easily avoidable money mistakes I ever made was unknowingly paying for not one, not two, but three Amazon Prime memberships for seven years. I somehow ended up with three separate accounts tied to three different email addresses. Each one was charging me about $15 a month. Over the course of seven years, that added up to almost $4,000.

I only found out because I succumbed to an Instagram ad for RocketMoney, thinking to myself, "who really has subscriptions that they don't even know they're paying for?" Me. I had subscriptions that I didn't know I was paying for… And I was paying a lot.

As soon as I discovered the triplicate charges, I called Amazon. Since the memberships were legitimate, they weren't obligated to refund me on the basis of fraud (despite how hard I definitely tried to convince them that I had no recollection of opening three accounts, and it surely couldn't have been me). Still, after explaining the situation — head down and tail between my legs — they graciously refunded me for a portion of the charges, totaling about $1,200.

The experience taught me three valuable lessons: Regularly audit your subscriptions, actually read your credit card statements (especially for recurring charges) and don't be afraid to ask for help, even if you don't think you're entitled to it. The worst someone can say is no, but sometimes, they'll surprise (and save) you.

— AnnaMarie Houlis, weekend editor

2. Straying too far from your non-negotiables when buying a home

When I set out to purchase my first home, I had a list of musts in my mind: it had to be over 700 square feet, have outdoor space, come with a parking spot, and be within budget with maintenance fees under $500 per month. Unfortunately, after touring dozens of units in a hyper-competitive early-COVID market, some of these quickly fell by the wayside.

While going into a home search with flexibility or even ambivalence isn't an inherently bad thing, it can have serious consequences. Personally, I ended up settling on a condo that failed to tick some boxes because I got caught up in the fervor of the market.

I convinced myself that shelling out a few hundred more than I'd planned for maintenance fees each month wasn't such a big deal because the building had an outdoor pool (which wasn't on my list of must-haves). I thought renting a parking space would be worth it because the sans-parking unit I chose gave me more square footage for my buck than others I saw that came with their own spot, and I'm now spending $300 a month on parking.

These compromises added up. My maintenance fees, already starting higher than I would have liked, have escalated. Add to that my parking, mortgage payments and property taxes, and I feel extremely behind.

I do have an asset to call my own at the end of it. But I may have fared better sticking hard to my criteria, or gradually putting the same amount into a different type of investment altogether.

— Becky Robertson, senior staff reporter

3. Using popular tax prep services by default

I used to file my annual return using TurboTax or H&R Block. I'm a big sports fan. And during tax season, seemingly every sporting event on television is sponsored by them.

The appeal is that anyone can file their taxes for free. But the truth is that, once you add certain tax forms or report a specific tax situation, the software automatically bumps you up to a paid tier. Only 37% and 52% of users actually file tax returns for free with TurboTax and H&R Block.

My taxes are by no means complicated, but I would still end up paying anywhere from $85 to $110 to file a federal and one state tax return. I always thought, "I can just pay for it with part of my return." I wish I could smack that 20-something-year-old version of myself now.

I now use FreeTaxUSA, which allows anyone to file federal taxes for free and a state tax return for $14.99. Cash App Taxes also lets you file your federal and one state income tax return for free, and Jackson Hewitt is great for filing multiple state returns for a flat $25 charge.

Not every online tax prep service will feel as seamless to use as TurboTax and H&R Block. But they're good enough to file your taxes on the cheap. There's definitely a few scenarios when using the industry-leading companies' services makes sense, but don't just start a return and hope for the best at checkout.

— Danni Santana, weekend editor

4. Failing to check credit card statements

When I was a younger man, I never paid any attention to my credit card statements. I figured I knew everything I was buying, so there was no reason to studiously review my bill every month.

Eventually, I did need to review my statements and noticed a $20 charge I didn't recognize. It was on the previous month's bill, as well — and the month before that, and so on for years. It turns out that TransUnion signed me up for a paid credit-monitoring service when I tried to get a free look at my credit score.

Since then, credit bureaus have been fined multiple times for deceptive "dark patterns."

In 2005, Experian paid $950,000 to settle FTC charges that it signed consumers up for paid credit monitoring without proper notice. Two years later, it had to pay another $300,000 because it kept running misleading ads for the service.

In 2017, the Consumer Financial Protection Bureau ordered TransUnion and Equifax to pay $5.5 million in fines and $17.6 million to consumers for deceptive practices. Five years later, the CFPB sued TransUnion for ignoring its orders, calling it an "out-of-control repeat offender that believes it is above the law." (That suit was dismissed in 2025.)

It all came too late for me. I was charged about $1,000 for a service I never used, and the company refused to refund the money. My lesson: Even if you're certain you're on top of your bills, check them anyway.

— Kevin Hamilton, senior editor

5. Not making the most of an inheritance

In my early 20s I inherited a modest sum of money — not a life-changing amount, but not insignificant either.

At the time, the sum of my financial knowledge encompassed basic bank accounts and retirement savings. But as I was so young, retirement saving didn't feel like a priority. A financially-savvy friend, however, advised me to invest the inheritance and even offered to help me pick stocks.

Of course, today the youngest Gen Zers eagerly invest via apps. But in the early 2000s, years before Apple even coined the phrase "there's an app for that," stocks felt like a game for older and wiser adults.

Intimidated and fearful of losing the inheritance on a bad stock bet, I balked and foolishly kept the money sitting in my plain old bank account. Over time, I chipped away at it for a splurge here and there, eventually using the remainder to pay my college tuition to study creative writing and journalism.

I don't remember a single thing — beyond an education — that I bought with that money. But I do remember the hard realization, a few years later, when I considered how much that portion of the inheritance that I spent frivolously could have grown if I'd invested it in anything worthwhile.

Paying for an education is never a regret, but I will always wonder how much further ahead I might have been if, back then, I had been more open to a financial education, as well.

— Mike Crisolago, senior reporter

6. Using credit cards as a crutch post-college

As a college graduate, I was determined not to fall into the "move back home and live in your parents' basement" stereotype. I was also, unfortunately, armed with a collection of high-interest credit cards I'd acquired when the companies came to campus to sign up a bunch of kids who had neither the income nor the knowledge to manage them.

I stayed in my college town, taking on the gigs I could find, including part-time work at Barnes & Noble, while I tried to figure out what to do with my life. My expenses weren't high, but the student loan income stream was over and decent job opportunities were scarce. I was broke, but I did have that plastic.

Perhaps you can recall the scene from the Gen X classic "Reality Bites" in which Winona Ryder's character uses her father's gas card to buy groceries. My situation was similar, only I was using credit to fund my whole life, including paying rent with very convenient (and dangerous) cash advance checks.

I ultimately racked up close to $10,000, and, when I could no longer make even the minimum payments, I admitted defeat and moved home. One year later, after I'd consolidated and paid off my debt with the salary from my first office job, I had an expert-level understanding of personal financial management that remains today. Sometimes youthful mistakes really do pay off — but if you can avoid making this one by never charging what you can't afford, all the better.

— Rebecca Stropoli, deputy editor