12 Real Women on Their Biggest Money Regret

Woulda, coulda, shoulda, but didn’t properly pad our emergency savings account. Whoops. We’ve all been there with money decisions we wish we could redo. Here, 12 women on the biggest money regret of their lives.

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college debt

The One Who Overspent On Education

“Because of crippling student loan debt, I regret not actively pursuing more outside scholarships for my undergraduate education. And, for graduate school, I wish I had just gone with a state school, not a private one. It’s really hindered our savings and ‘fun’ travel down the line.” — Jenny, MA

woman by pool

The One Who Couldn’t Budget

“I used to spend, spend, spend—say, on a vacation—then, when the money ran out, I’d cut myself off from buying anything at all. I wish I had been more conscious of budgeting and had rationed my cash, instead of blowing each paycheck all in one shot, then living dollar to dollar until I got paid again.” — Sarah, KY


The One Who Didn’t Know About Fsas

“I regret working for 12 years before learning about flex spending accounts. By putting $5,000 in pre-tax money into a dependent care FSA—which I then use to pay my son’s preschool bills—I save something like $1,500 annually.” — Arianna, NY

couple on laptops

The One Who Never Had Her Own Bank Account

“I got married very young at 23, so I feel as though I never got to really manage money on my own. I’ve always worked, but I was never financially independent, and money dealings with my husband almost feel incestuous—we share everything and lines are blurred. It’s a hard habit to break!” — Karen, NY

woman in apartment

The One Who Put All Her Eggs In One Real Estate Basket

“We bought an apartment in April 2008 at what we thought was the bottom of the market during the recession. Then, six months later, I was told to take a pay cut or lose my job. Then, the condo had to do a special assessment because the developer declared bankruptcy on the unsold units in the building and we had to cover their utility costs/taxes. Then, the city raised the taxes due to the recession. We ended up selling it at a loss to get out of crippling debt and moving to a new city for better jobs. We also put off having kids during this time and, later on, had many, many troubles due to our age. So, I’d say, you can’t plan for that many rainy days, but I regret assuming real estate is the best investment.” — Monica, GA

couple getting married

The One Who Paid For Her Wedding With Credit

“I wish we had explored taking out a loan to pay for our wedding. We put a lot on credit cards and it took years to pay them off. I absolutely loved our wedding, but I wonder if it could have been financed differently.” — Emma, NH

woman paying bills

The One Who Started Late

“I regret not investing younger—i.e., when I was in college and had some fluff money without any bills that could have been giving me compounding interest. If you ever run the numbers, the difference between how much money you have when you start investing at, say, 18 versus 22 years old is astounding.” — Genevieve, NY

credit cards

The One Who Had A Thing For Points

“I regret generally misusing credit cards at an embarrassing age and just not taking the time to understand how important strict budgeting and payment strategy were. The painful fall back down to reality came when I thought I was being so slick and got a credit card where you earned a chunk of points if you spent X amount in the first couple of months, which I did—and kind of put myself into a hole by doing it. And those points I racked up? The problem was I had the card linked to my Amazon account and you could spend the points there. I ended up blowing all the points that I was ‘saving for travel’ on stupid Amazon purchases. When I realized what I had done, I cried for an hour.” — Caroline, CO

three people meeting

The One Who Got Scammed

“My husband and I totally fell for one of those scams where a nice woman came to our house and convinced us that if we switched gas suppliers, then we could save hundreds of dollars a month. We invited her in, chatted for ages and, yep, switched. Then, low and behold, our next bill came and *of course* it went up, not down. We always thought that we were too smart to fall for something like that but, um, apparently not. We switched back to our original supplier the month after, so it was fine, but still. Annoying lesson learned.” — Lauren, NY


The One Who Blew Her Retirement Fund

“I cashed out my 401(k) to go to a destination wedding in Ireland. Loved the wedding, but now I wonder: Will I ever be able to retire?” — Laura, MA

woman studying

The One Who Padded Her Student Loans

“I took out more student loans than I strictly needed, which built up an intimidating total and has taken years to eliminate. I’m almost done now, but I would probably reconsider grad school entirely if I had a do-over.” — Carolyn, CA 


The One Who Missed The Crypto-boat

“I wish I had bought a bunch of Bitcoin when it was super cheap. I actually researched how to do it and everything and then just never did it.” — Marta, MA

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Royal family expert, a cappella alum, mom

Rachel Bowie is Senior Director of Special Projects & Royals at PureWow, where she covers parenting, fashion, wellness and money in addition to overseeing initiatives within...