Recently, redditor u/ALLEYWAYwithanS asked, "What’s the dumbest thing you’ve done in your 20s?" People shared the biggest mistakes they made in their 20s, and TBH, you may want to take notes. Here are some of the most surprising responses:
1. "I decided against contributing to my company's matching 401k. It cost me hundreds of thousands of dollars."
"This can't be stressed enough. If your company is matching 401k contributions, the single best thing you can do is contribute up to their match. That is an instant 100% return on your investment. Social Security benefits will not be enough for you to retire comfortably, and when you're over 50, it gets really tough to find work that pays more than minimum wage. Make saving a priority now. The sooner the better, because it is a cruel world for unprepared retirees."
2. "My general lack of effort to build any good habits like exercise. Your body likes routines, and my routine of gaming for 15 hours a day was not one I should have cultivated."
"I'm in my late 30s and had stopped any sportive activity in my 20s. In my early 30s, I spiraled into a major depression and basically didn't move at all for, like, five years. Three years ago, I got better mentally. Two years ago, I finally got myself to work out again (after a solid year of aches and pains because turns out, our bodies like moving and dislike not moving for years). I gained about 33 pounds of weight since then, and my general fitness, strength, and well-being have never been better. I'm still ways from where I want to be, but I'm proud of how far I've come. And if I can still make those gains at nearly 40, you can definitely do it in your 20s."
4. "I assumed climbing the corporate ladder is the way to do life."
"Spent my 20s and early 30s doing the same. I made great money, but I had no life, and I was completely miserable. I left my corporate job at 34 and took a huge pay cut to work at a nonprofit that locates and provides safe affordable housing for people with disabilities. I make less than half of what I used to, and I’ve never been happier. Money really isn’t everything."
5. "I had good teeth for most of my life, until I fell into a very dark, depressed place in my late teens and early 20s — at which point, I didn't care about anything, including my teeth. I got the help I needed a couple of years ago and have been doing much better, mentally speaking, since then, and I've been taking care of my teeth. I do all the right things: brush twice a day, floss, avoid sugary drinks, etc., but no matter how hard I try to stay on top of them and keep them in good shape, they're continuing to get worse as I haven't been able to get the previous damage fixed due to financial reasons (dental work is expensive AF). Moral of the story for anybody reading this: TAKE CARE OF YOUR TEETH, or you WILL regret it!"
"There is no worse feeling than being genuinely afraid to smile and show your teeth. I haven't smiled with my teeth in a couple of years now. Additionally, when I talk to somebody, especially someone new, I try to move my mouth as little as possible to avoid them seeing my teeth."
6. "I worked way too hard and burned out. Sacrificed family time. Sacrificed health. You need to pace yourself at the age of 20–30."
"This is me right now. I'm 29 and totally burned out. I refused to pace myself even with my chronic illness, I refused to address my traumas because 'I'm a functional member of society so why would I seek a therapist,' and I refused to say no to things because I was afraid people would dislike me. Last year, I slowly started collapsing under all that. Things I repressed wouldn't stay repressed and caused nightmares; I had constant panic attacks when I got home from work and eventually bordered on agoraphobia where I would try and flee the grocery store because 'everyone can see you are feeling unwell and is judging you.' I started making excuses to work from home because the office would overwhelm me. I really wish I started addressing things sooner. I tire so easily now and am constantly anxious about not being productive enough now that I'm at home — which is super counterproductive when your body is saying, 'Slow down. Please go find a nice hobby and relax.'"
7. "I took powerlifting way too seriously. I spent seven years in gyms for hours every day, skipping every social occasion and holiday. I didn't get as strong as I wanted to. I just got all sorts of physical issues to deal with for the rest of my life now."
8. "I moved in with a girlfriend before finding out more about her preferences. We had been dating for a year, but I didn’t realize how much of a problem she had sharing until we lived together. We did for five years and never shared a bedroom, had everything split down the middle including the pantry and fridge, and even when it came to spices, she insisted on me getting my own. She hated it when I would be in the same room as her unless it was under 'her terms.'"
"Whenever I asked to make our relationship more of a shared experience, I was gaslit into believing I was wrong for not allowing boundaries. She moved out a month ago, and I couldn’t believe how quickly my mental health improved simply by not having that toxic influence around anymore."
9. "I regret not getting help for my depression sooner. Spent the entire first half of my 20s in the darkest place I can imagine, and all I needed to feel better was some meds once a day."
10. "Not studying properly. At the time, studying for two to seven years seemed like a lifetime, but now at 30, I wish I had done it. I don't have the money or flexibility to do it now."
11. "I drank my way through my entire 20s. After 25, it wasn't really fun anymore, but that didn't stop me. Drank for another five years. My 20s are a total blur splattered with some fun times here and there, but it was mostly just me running away from things with alcohol. Almost 17 years later, and I haven't had one drop. My 30s and 40s are exceptionally better."
12. "I got married to the wrong woman. Never get married to someone who isn't sure if they love you. That person is damaged and needs space."
"I just broke up with someone after being together seven years. I could tell from the beginning there was something wrong, but I chose to ignore it. I was the one pushing the relationship forward. In the end, she realized she had missed out on going out and partying with friends, and that was it. We never got married or had kids, but it still hurts. But yeah, I could have enjoyed those years and not have wasted it on someone who didn’t love me back the same."
13. "Ran up $11k worth of credit card debt over about 18 months when I was 25–26. I didn't become debt free until I was 33 and never had an excellent credit score until 36."
14. "I broke up with (what may as well have been) the greatest girlfriend I've ever had. Three years later, I'm still single, and I think about her from time to time."
15. "I do have a fully functional life, but in my 20s, I definitely missed out on those basic experiences one should live at least once in life. I'm talking about taking an international trip, or going to a concert, or trying to get new friends and such. I mostly followed an unreachable professional dream, which was such because I never intended to move out of my comfort zone in the first place, and then found some refuge and gratification in lonely hobbies I experienced at home."
"It took me a huge amount of guts to get out of that pond and start living a bit. Deeper inside, I still pay the price of such inaction today, and having professional and family responsibilities now doesn't help."
16. "I didn’t ask for help when I got in trouble financially. I was sucked into payday loans, eventually owing thousands; it got so bad that my payments were more than my wages. I'm still struggling now, but I'm almost there."
17. "I dated the wrong people for access to sex. I knew at the time they were problematic, and it led me on a path of a lot of trauma and having the wrong view of the world. That took a while to dig out of."
18. "I regret continually denying my abilities and skills to be 'humble.' After a while, I started to believe that I was, in fact, worthless — do nothing, be nothing. I hit 30, and it was like a switch went off. I saw everything objectively, and turns out, I'm a pretty great dude. Mistaking self-doubt for humility is a pretty messed-up poison."
20. "Drinking and driving. A lot. Never got busted. Quite stupid. I am now five years sober (unrelated). I say this from the bottom of my heart. There are friends, taxis, Uber, Lyft, etc. ... Utilize these for yourself."
21. "Going straight into grad school was such an awful decision for me. I came out of undergrad completely set with no debt, ready to move to the next stage. I really wanted to pivot to a semi-related field, and I graduated in 2020 (R.I.P. job market), so I decided to go and get a master's. I wasted a year and a half of my life, took on tens of thousands in debt, and then dropped out because I realized I hated my new field, and student life was making me extremely depressed."
"I got a job with my undergrad degree a few months later and am doing much better now, but it pains me that I could've just waited that whole time, and I would've been better off financially than I am now."
Do you relate to these? What are some of your biggest regrets from your 20s? Let us know in the comments below.
Note: Some responses have been edited for length and/or clarity.