Real Women Reveal Their Biggest Money Mistakes—And What They Wish They’d Done Differently

This expert advice will give you a new financial philosophy.
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Ask the average American if she is concerned with her financial situation, and you'll likely get a resounding yes. In fact, a shocking four in five people have money regrets that keep them from financial peace of mind, according to a recent Bankrate survey.

"Worry and anxiety is so common that we get used to feeling that way—especially about our finances," according to Leanne Jacobs, a wealth expert and author of Beautiful Money: The 4-Week Total Wealth Makeover. That's certainly the way the five women we spoke to for this piece feel—anxious, overwhelmed, and regretful.

"But it doesn't have to be this way," Jacobs says. "If you are feeling anxious and stressed on a regular basis about your money, it's time for a new philosophy."

So we took a look at Americans' five most common money regrets—as discovered by this survey—and asked finance experts how we can keep calm and move on, even feel better about our financial futures. Read on to rid yourself of money regret.

Regret #1: Not saving for retirement early enough.

Chelsea Hudson, 26, started saving for her retirement two years ago—much earlier than the average American begins to sock away money for their golden years. But even so, the Montclair, New Jersey, woman worries she still isn't saving enough.

"Even though I am still in my twenties, I fear that I won’t have enough money saved for retirement," she tells Glamour. "I have a handful of friends who haven’t even started a 401(k) yet, and that scares me. One of the main reasons I believe women my age don’t start saving is because they can’t fathom the future—we all want to live in the present. Even though it's inevitable, I can't imagine being 65 years old and retired."

Hudson has hit the nail on the head for the reason why many women don't save up for the future, Jacobs says. "Let's be honest: We're unlikely to prioritize retirement savings over an impulse spend because it doesn't give us that [present] high," she explains. But "the trouble with not saving for retirement early enough is that we get stuck living in fear. One of our greatest fears is a lack of financial security, so when we don't take actions in a positive financial direction, we get caught feeling stressed and anxious—chronically."

But just because you've delayed saving for retirement doesn't mean you can't start, stat, by automating your retirement savings. "Set it up once," says Jacobs, "and you won't even notice the money transfers taking place. You will feel empowered and proud of taking control of your future." Bonus: "What will make you feel even more empowered is increasing the amount being transferred to your retirement savings every time you get a pay increase or attract more cash flow," Jacobs says.

Regret #2: Not saving enough for emergency expenses.

"My biggest financial regret is that I didn’t put more money aside for unplanned medical expenses," admits 47-year-old Kaye Newton of Nashville. As with many other Americans, Newton's health insurance deductible is high—like, $8,000 high. And when she had an unplanned surgery, her out-of-pocket costs climbed to a whopping $36,000. "I am extremely grateful for my health insurance," she says, "but I was physically stressed by the operation and mentally stressed when I saw the bill. That money could have gone to my kids’ college savings accounts or helped pay our bills."

The thing about emergencies is, they always seem to happen to someone else—until, of course, they happen to you. And when you're hit with an unplanned expense, such as a medical emergency or car trouble, "most Americans end up taking on high-interest debt or derailing their financial plan," says Elle Kaplan, finance expert and founder of LexION Capital. So it's no wonder we regret not saving up in advance.

However, "you’ll never regret setting money aside for a rainy day," says Kaplan, "so you should start building an emergency fund now. By setting aside six to eight months of bare-bones living expenses, you’ll be able to coast through a job loss or an emergency without financial damage." That seems like a big number to save up to, we know. But "an easy way to start is to automatically have part of your paycheck transferred into your savings account," says Kaplan, even if it's just $20 each week.

Regret #3: Taking on too much credit card debt.

When 28-year-old Cassandra Williams was out of work for a six-month stretch, "I charged bills to my credit card," the Rocky Mount, North Carolina, resident says. And when she couldn't pay back her credit card debt in a timely manner, Williams's credit score took a hit. She paid off that debt when she got a new job—but the comfort of a regular paycheck also made Williams comfortable enough to take on another $6,000 in debt, "just by not keeping an eye on my statements every month and forgetting to pay more than the minimum due."

Like Williams, many Americans don't keep an eagle eye on their charge cards, which allows debt to pile up—and causes serious buyer's remorse. "Who hasn't binged on shopping, travel, or a little luxury at some point?" asks Jacobs. But "the red flags fly when spending on credit becomes a pattern." So, instead of spending now what you hope to be able to afford in the future, Jacobs suggests pulling out a credit card only after you've earned the money to pay the bill. She says, "I focus my energy on using my creative powers to make the cash and then reward myself with the spend."

Another way to reduce credit card debt in the future is to limit yourself to carrying just one card, Jacobs says. "I also suggest calling your credit card company to lower your spend limit," she suggests. "Make it very difficult for yourself to binge-spend."

Regret #4: Taking on too much student loan debt.

San Diego resident Maresa Friedman, 34, says she wishes she'd never gone to college. "Even now, I’m swimming in student loan debt—and my degree seems worthless," she admits. "It feels like a weight, and based on the current business climate, seems like a waste." The debt she carries for her education also makes her worry about her daughter's future. "I worry about not being able to save for my daughter's college," Friedman says. "It keeps me up at night, thinking that probably around the time I finish paying off my loans, I’ll have to incur more debt in order to send her to school."

If you're considering taking out student loans, consider how you might be able to save yourself a big headache after graduation day. "Many Americans ignore the opportunities to save money on college, because they think it somehow cheapens their education," says Kaplan. But before you treat your loan as carte blanche, "realize there are ways to save money that won’t change the quality of your degree."

One way to save on student loans might be to live off campus, rather than pay for a dorm and the meal plan that goes with it, Kaplan says. "That off-campus apartment could save you tens of thousands down the line," she points out. You can also search for grants and scholarships—"millions of dollars of which go unused each year, just because most people ignore opportunities to save," Kaplan says.

Regret #5: Not saving for your children's education.

Speaking of expensive college debt, many Americans—like 39-year-old Blair Critch—regret not setting aside more money for their kids' educations. The idea of not being able to provide for their education costs seriously stresses her out. "Tuition rates go up, cost of living increases, and there will be unforeseen circumstances you simply can’t plan for," Critch, of Fort Lauderdale, Florida, says. "I want to be a great mom and lay a solid financial foundation for my children, and I know the way that we manage our money will directly impact—good or bad—the course of their lives."

But both Kaplan and Jacobs agree that you have to help yourself—taking care of your debts—before saving up for your kids. As Kaplan points out, "airlines tell you to put on your own oxygen mask before assisting others for a good reason; you can’t help others if you don’t help yourself first. You shouldn’t regret not saving for your children’s education if it harms your own finances." Plus, "there are many grants, loans, and scholarships available for college, but none for retirement," she says.

That being said, if you're intent on saving up for your kids' college experience, "book an appointment with a financial adviser who can walk you through options and alternatives for starting an education fund today," Jacobs suggests. "Find out about the financial advantages of starting an education account today."