Living With Debt

15 People Share Their Biggest Financial Regret (And What They’re Doing To Fix It)

By | Friday, November 13, 2015


This week, I set out to ask people about their financial regrets, and I don’t think I realized how diverse the answers would be until I started asking. It was an important reminder that many of us, regardless of where we are in our professional and financial lives, have what we deem a “financial regret.” However, as we get older, or change professions, our regrets, and our solutions start to evolve with our lives. Something that seemed like a disaster when I was applying to college no longer seems relevant now, because I worked through it. And I am sure that in 10, or 15, or 20 years, some of the financial mistakes I’ve made this year will be brought into perspective. This doesn’t mean that our financial regrets are more or less significant than anyone else’s. It just means that we all can learn something from each other’s regrets and solutions.

I asked 15 people (from ages 24 to 63) what their biggest financial regret was, and how they are trying to fix it. Here’s how they answered:

1. “One big financial regret I’ve always had is throwing money away on guys. I would blow $100 on a bus ticket to visit my long distance college boyfriend on the weekends and he wouldn’t chip in, or pay to come see me. Not to mention showering guys I was involved with in gifts and such to show them I cared for them. It was as if monetary gifts could win their affection. And I’m not just talking gifts, like a book or movie. I’m talking expensive things, and good clothes. How did I fix it? I finally found someone who could take care of and support himself. Of course we’ll buy each other things here and there, but we’re never trying to win each other’s affection with gifts.” — Laura, 25

2. “My biggest financial regret is that I never took ownership of my money. My family had very little growing up, so I delivered newspapers so I could give my parents money to contribute to household costs. Then in college, I was still giving money back to my parents. In my marriage, I was having my husband deal with the money entirely. I was so used to handing over the money all of my life, that I didn’t know how to keep it for myself or manage it. I finally realized that I’d been trained to always hand my money off instead of dealing with it myself. Slowly, I learned, and I made mistakes, but I figured out how to help manage our finances, and I turned my behavior around.” — Mary, 40

3. “My biggest financial regret, to date, is moving in with my significant other of three months. When we moved in together, I made more money. I bought all of the furniture, and paid the full deposit on our apartment. A year and a half later, after fighting on and off, we broke up, and it wasn’t a super amicable split. I moved home for a little while, because at the time, I was out of a job. She got into a union, and is now making double what she was when we lived together. I’m happy for her for doing well, but when we were together, I covered all of our expenses, and now I’m out of work, and she’s doing well financially. I don’t regret the relationship, but I feel like an idiot for the fact that I spent all that money, when I should have been saving. To fix it, I’m still at my parents trying to save up.” — Sam, 29

4. “I am young still, so I don’t have too many financial regrets, but I regret that I haven’t opened up a 401(k) with my company yet. I was offered the opportunity to open one two years ago, and haven’t taken advantage because I didn’t want to lose the money from my paycheck. As a solution, I’m finally signing up this year.” — Taylor, 24

5. “I absolutely, without question, will always regret agreeing to move into an apartment where the rent was over half of my monthly income. I couldn’t afford it but was swooned by a fast-talking leasing agent and impressive views. I said yes to the apartment when I should have said no, and was paying way too much in rent. I was constantly stressed about money because of it. In the end I learned to do my research with homes diligently, to never be afraid to negotiate, and to learn to say no – even when the bells and whistles of a pretty place make me want to say yes. I finally had to get a subletter for that apartment and move before the lease was up.” — Kayla, 26

6. “I have had three major medical bills go to collections in the last few years, and there is no reason for it, other than that I am disorganized. As soon as I got the collection notices, I verified them with insurance, and my doctor’s and then paid them off immediately. While it isn’t the biggest financial regret compared to some, it could still factor into my credit score. I hate that I ran the risk of them showing up on my credit report (so far only one has), and I have learned that going forward, I need to be more diligent about each payment. I try to keep files of everything now, and track each bill as it comes in.” — Alexa, 30

7. “I graduated with no student debt. I had a major scholarship in college, and apparently, never learned to manage money well. I moved to a big city after college without a job. I borrowed money for the move from my parents. I went into credit card debt while job searching. Then I finally got a job, paying much less than $30K a year, but went out constantly, because I worked in an industry where everyone went out a lot. I racked up about $5K in credit card debt, before realizing I was in huge trouble. As a solution, I realized that the industry I was in wasn’t for me — it was shitty pay, and I didn’t want to move up in my job. I applied like crazy, and found a job that paid more money. I am using my new salary to pay off my debt, and am limiting my spending habits..” — Eric, 26

8. “Honestly, I regret not going to community college, or state school. I got almost a full ride to a state school in Massachusetts, but I went to an expensive school and am now about $90K in debt. There is nothing to be ‘fixed’ now, though I made a wiser choice financially for grad school, so I guess I am learning from my under grad loans in that respect.” — Gabbie, 24

9. “In college, it became very easy to request financial aid and receive it without too much issue. I quickly learned that, regardless of my real need, I could get more money than I needed just by asking for it. It became so easy to ask for an extra few thousand dollars ‘just in case’ I needed it for books or incidentals (which I was lucky enough to have my parents cover as long as I kept my grades to As and Bs). I never needed the money for books, so I kept getting a little extra every time I had to apply for financial aid, and used it as spending money. That was the most expensive spending money ever and my biggest financial regret. I have guilt about my bad judgement, even now. I fixed it by paying for my purchases for years after the fact, and learned the consequences of borrowing unnecessary money to spend on unnecessary things.” — Christina, 35

10. One big mistake I made is how I used some of my inheritance. My grandparents and great aunt left me moneys when they passed. I used it to pay off some of my student loans. Obviously, this is a good financial choice, and I’m thankful I got a jump start on my loan payments. However, I put all of the money toward my student loans, and I wish I had put some in savings. I had very little savings, and I wish I had used some of the money as a cushion, or an emergency fund, in hindsight. I am now growing my savings, but it has taken two years — because that’s how long it took to get raise at work.” — Jenn, 25

11. “My husband and I bought our house using some of my student loans and grant money. When we were married, paying my loans took a back seat to other things. We ended up getting divorced, and we still hadn’t paid my loans off. After our marriage ended, I went back to paying my loans, and it was terrible to be paying off some of those loans knowing that I was actually paying off some of the house we used to live in together, and purchased together. It was a mess. It took me 10 years to pay off my loans, but I finally did. And I guess you could say that’s how I fixed it.” — Gina, 43

12. “My biggest financial regret (so far) was getting a credit card in undergrad and using it unwisely. I ended up not really knowing what I even spent that much on. Thankfully, my credit limit was low, but I reached the max all too quickly. I started with good intentions (building my credit) but ended up losing track of my expenses. I know for a fact that I ended up buying things like clothes and booze which I could have completely avoided. To solve my problem, I made a goal to pay it off before I finished grad school, and thankfully I made that work.” — Emma, 25

13. “I regret not asking for shares in the startup I worked for years ago. I cannot share the name, but I invested so much time and effort into that company, and was not compensated very well. I was one of the people that made that company successful (and helped) but after a few years, it was time for me to move on, and make more elsewhere. They eventually turned very profitable, and I got no residual money, no shares, no nothing. I don’t feel like there’s anything I need to do to rebuild, I just need to know to stick up for myself next time.” — Matt, 31

14. “I didn’t start saving for retirement until I was almost 40. In some respects, I am very much a cautionary tale, because I have not been able to retire yet, and won’t be able to for a few years because I started saving late. If I could go back, I would’ve started saving at least ten years earlier, if not more.” —James, 63

15. “I would say my biggest financial regret is holding on too long with a company I should’ve let go of a long time ago. I knew they were starting to do poorly, but I stayed out of loyalty. Then I knew they going to have to cut my pay, and I still stayed. I stayed until they let me go, which only happened because it was absolutely necessary. As a result, I don’t have a job now, because I should have been applying six months ago, and instead I’m applying now. In order to fix it, I’m trying to hustle as much as possible to find work, whether it’s full-time or just projects on the side.” — Curt, 27

Image via Unsplash

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