A few weeks back, I somehow stumbled through the labyrinth of the internet to find an article where people revealed their juiciest money secrets and financial fears through an app that allowed them to remain anonymous. Some of the confessions were raw and brutally honest, some were inspiring, and some were straight-up facepalm bad. Sometimes it feels like I am alone in slipping up and doing stupid things with money — surely others can’t have as hard a time as I am having with this particular thing, right?? The article linked above was short, but it was a powerful reminder that everyone has their own financial baggage and set of issues they’re working through. I had to pick a few of my favorites to share below to illustrate the fact that we aren’t alone in our deeply-shameful financial regrets and mistakes:
“I got quite wasted last night and apparently got the genius idea to pay off all of my credit card debt. It feels great to have paid off $10k+ in debt, but it feels extremely stupid to have $784.64 to my name.”
As I read that one, I reflected on all the silly stuff I’ve done at the end of the night after a few drinks (online shoe shopping anyone?), but this confession took the cake. Another brutally honest one was:
“My fear is never making enough money for my son and I to move out of my parents’ house and move in with my boyfriend. I’m 27 years old.”
A really candid financial fear that, to me, illustrates the social stigma and strain that people feel when they can’t hit milestones people around them are hitting. I, myself, was 25 years old when I moved out of my parents’ house, and I felt ashamed that it had taken me that long to move out. I can only imagine how frustrating it must be to have a child and still be living at home. Another financial mistake someone admitted to was:
“I replaced my roommate’s Ralph’s reward keychain card with mine so I get extra point for his spending.”
LOL. There’s something so innocent but also extremely calculating about this one, which I love. It reminded me of all the times I stole my roommate’s snacks in college because I was too lazy/cheap to go out and buy my own. The list is definitely worth checking out in full here, even if a lot of entries on that list are confessions than they are mistakes. However, the roundup really got me thinking about the things people do wrong but are too ashamed to admit to, even if they’ve learned from their mistakes and are wiser for having made them. There’s still something painful and embarrassing about coming clean with financial regrets.
Below, I got five women to reveal their biggest financial mistake with the peace of mind that they would remain anonymous. Take a look!
1. “I paid my Craigslist roommate more money for rent than I owed because I never asked to see paperwork. I’m so fucking stupid. I wanna kick myself because I made such a huge mistake when I was first living on my own with strangers I didn’t know, and it still makes me feel like I can’t trust people. Originally, I lived in a multi-family apartment, but it was bought by an investor and we were told we had to move out ASAP. I was desperate and definitely didn’t do enough research into apartments I found on Craigslist. I was stressed out, on a tight timeline, and thought nothing (too) bad could happen. When I went to see the apartment, I think the guy realized I was naive and in a tough spot, and he offered me the room, said I could move in as soon as I needed, and that he’d charge me X rent per month. So I moved in, paid him each month through Venmo, and didn’t think much of it. About a year later, I for some reason, asked the third roommate was she was paying. We had the exact same rooms, and the number she threw out was much lower than what I paid. I couldn’t believe it. All this time, I was supplementing this dude’s portion of the rent. It was my stupid mistake because I never asked to see the paperwork…never bothered to do things the right way, and I paid for it big time. I got into a shouting match with the guy who refused to reimburse me, and I moved out a few weeks later. That shit still makes me SO mad.” — Monica*
2. “I didn’t financially prepare for a long-distance move, and now I’m working at a pizza shop (but nobody back home knows). I was 23-years-old and really unhappy with my life. I went on like, a six-month rant about how much I hated living in my hometown, how lame it was, and how I could NOT wait to leave after college, blah blah. I chose to fixate on a random city a six-hour drive north of where I lived. It was much bigger and offered more job options (or so I thought). I was so obsessed with leaving after school that I barely saved any money or prepared for the possibility that I wouldn’t be able to find work right away. By the time I finally packed up my stuff to go, I had alienated most of my family and friends. After laying into where we all lived so hard and shit talking it for so long I couldn’t blame them, but I just couldn’t keep it inside. I thought I would choke to death in the suburbs. Once I moved, I quickly realized that I had not put enough time into looking for work before I got there — I was like a month deep into the job search with absolutely no leads. I ended up having to take a job at the local pizza shop to make some money. I didn’t want to drain the precious little savings I had, and I was too embarrassed to tell anyone what was going on. That was seven months ago…I really fucked myself over by not planning ahead.” — Emma*
3. “I forgot about a line of credit I opened a year ago when I bought myself a new laptop, and sunk my credit score. When I went to go buy myself a new laptop for my senior year of college, I signed up for a credit card that allowed me to put the purchase on it and not pay a single dime for six months. Well, I opened up the line of credit, took the laptop home, and must have lost a massive chunk of my brain/memory at the same time. I was so caught up in school, graduating, and the prospect of joining the workforce that I never noticed the credit card company never sent me a hard copy of the credit card. I gave them an address with a typo (DAMNIT, typing into those iPads at checkout), and never received any bills OR the physical card. I forgot about it entirely until nearly a year had gone by (if you can believe it). Then one day, I heard someone next to me mention the credit card I used to buy the laptop. Suddenly, in horror, it all came flooding back to me. I shrieked, frantically called the company, explained the situation, and FINALLY logged into the account I had started so long ago. I was slammed with late fees, notifications, and alerts, and my credit score took a nasty hit. It was the MOST absolute idiotic thing I’ve ever done, and I’ll be paying for it for a long time.” — Serena*
4. “I could afford to work for free, and mistakenly told my friends. So, this might not be a traditional ‘mistake,’ but it’s definitely a financial snafu I made a few years back, which has haunted me forever. I’m a self-admitted ‘trust fund kid.’ Yes, my parents have a lot of money, and no I’m not too proud to take some of it. My parents gave me an allowance each month for as long as I can remember. Yes, it’s not a TON of $$$, but I lived with a roommate in a small apartment and spent pretty little considering how much I could be spending. However there was one thing my friends would’ve hated me for if they knew — I didn’t need to work full-time. I was able to work for free part-time job at a non-profit. Flat out, I didn’t need as big a salary as my friends did to make ends meet, so I got to do what I wanted with some of my time. However, after too many drinks one night, I made the fatal error and let the secret slip to my friends. *Insert cricket chirping sounds here*. The conversation came to a screeching halt. They felt enormously uncomfortable at my privilege and angry that I didn’t tell them about my situation earlier — I essentially lied to them every time I said I couldn’t ‘afford something.’ Looking back, I don’t blame them, but I also felt like it was something I didn’t want to hide forever I guess. We aren’t friends anymore, and I do regret lying to them about it. Sigh.” — Ana*
5. “I used to sell my ADHD medication to people to buy myself expensive things I otherwise couldn’t afford. This is definitely anonymous, right? The biggest financial mistake of my life was made during my college years. I made money as a drug dealer essentially. Basically, I had been receiving medication to treat my mild case of ADHD ever since I was in high school, and I didn’t realize how hot of a commodity it was until I got to college. People would always ask me if they could buy one or two pills off me during exam time, and at first I’d say ‘no.’ However, after saying no to the offer but then having to pull longer hours at my job to make extra money, I put two and two together. If I sold X percent of my prescription to my friends, I wouldn’t have to work extra at my job — I could focus on school stuff instead. I had wanted to stop taking the meds anyway, so I was easing myself off of them very slowly. (This should go without saying, but I realize now that this is totally inadvisable and stupid…I was young and dumb.) It was so tempting to make extra $$$ and buy myself nicer clothes. I wanted nice things! I wanted designer makeup! I wanted to grocery shop at fancy markets like all my friends did! That financial tension led me to make bad choices. I used to rationalize what I was doing by saying, “these people are going to get their hands on it anyway!” I thought, as their friend I could at least keep an eye on them and make sure they were okay and not abusing anything. That logic fell through after six months or so, and I felt way too guilty to keep it up.” — Leighanne*
*Names have been changed
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