"I Didn't Know Until My Late 50s": 18 Mistakes Adults Over 30 Were Surprised To Have Made And Deeply Regret

People aren't magically perfect when they turn a certain age, but sometimes when you make a mistake, there just might be a feeling of "Wow, I should have known better." Recently, redditor u/otherworldly_mirror asked people to share the regretful mistakes they made when they were 30 and beyond that they couldn't believe they were capable of making. Here are the responses that emphasize that no matter what age, people are still learning along the way:

1."I took out student loans to go to college after I got clean. I was able to get my degree, but now, I'm in my late 60s, and I still have $46k in student loans. I'm not willing to work until I die just to pay them off, and my current job doesn't have anything to do with my degree. I don't have anyone to blame but myself. I'm still pissed that I didn't know enough about money management until I hit my late 50s."

A woman is paying with her credit card
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2."Believing I could get a guy to change if only I was 'good enough' for him. Oof."


3."Not getting myself out of a long-distance commute in my 50s, which, looking back, probably caused me to retire sooner than I otherwise would have. I love working on cars, but gripping the wheel for all that time worsened the arthritis in my left hand, so I had to stop."

A man is frustrated and stuck in a traffic jam
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4."Getting involved with a coworker. I was in my 40s. I can confidently say I'll never, EVER do that again."


5."Ghosting a potential romantic partner (I was 39, basically 40). We'd just gone on a couple dates. I should have said I wasn't interested, but I just let it lapse due to sheer laziness and fear. The guilt I felt was overwhelming, and I still feel bad about it. I'd never do that ever again."

A woman is staring at her phone

6."I stayed with a company for over 15 years and then was told I wouldn't be getting any raises going forward because I was at the 'top end of the range.' It's my biggest regret because I foolishly thought loyalty meant something."


7."Throwing myself into work and not being more present for my family. You can't ever get that time back."

A family is gathered around the dining table
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8."I started doing cocaine in my early 40s. I lost everything — my kids, my dog, my house, my cars, and a whole lot of money. I had to move away from my home state. I've now been clean for about 16 years."


9."A couple years ago, I made the mistake of letting an ex-friend weasel her way back into my life. She came with all kinds of reasons and excuses for her bad behavior in the past and claimed that she'd changed and had gone through therapy. I figured I'd give her a second chance. Within a year, she was doing the exact same things, but even worse than before. After calling her out on her behavior, she went totally ballistic on me, so I dropped her again."

A woman is sitting in her kitchen looking distraught
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10."Getting married. I've been happily divorced now for 14 years. I'll never make that mistake again."


11."Using people for sex. I specifically regret not being more gentle with people's emotions and being more honest about mine. I wasn't a 'womanizer,' but there were a couple of occasions when I knew I would seriously break a great girl's heart, and I did it anyway. I'm ashamed of myself for doing that."

A couple is lying in bed together with their feet tangled up
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12."I financed a new luxury model vehicle, and that ended up causing me to extend how long I had to work before retirement. I was such an idiot; that money would have been much better utilized in my retirement savings."


13."When I was in my early 30s, I landed a job that had a decent boost in salary. My regret is becoming complacent and, due to my low self-esteem, not taking my career any further and assuming that was as good as it was gonna get. So for 20 years, I treaded in the waters until I was laid off. If I could turn back time, I would have spent those 20 years networking, job-hopping, and aggressively doing everything I could to advance my career."

Two men are on their computers in the office
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14."I still make friends that I am not compatible with. I get into friendships with people who use and abuse me, or who force me into having relations with them. Most of the harm done on my mental health has been caused within the last six or seven years by narcissistic or dismissive people. They latch onto you and don't let go. I need to stand up and cut them off immediately."


15."Not getting a college degree in something useful and lucrative. I actually managed to do okay with my English degree, but I like money, so I regret not putting in the effort to enhance my money-making capabilities."

A woman is at her graduation ceremony
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16."I left my husband and three young children for a douchebag. It was a good 30 years ago, and my kids are now adults. I will never forgive myself for abandoning my family."


17."Not taking the time to learn about myself and understand who I was before getting married. This was a mistake I'd made in my 20s, but I did the same thing in my second marriage during my 30s, and for the third time in my 40s. I am still married to my third husband, but I really do appreciate my alone time."


18.Last but not least: "After a heart-wrenching divorce at 50, it wasn't until three years later that I started dating again. Though I vowed to be careful going forward, I got involved with a partner who went on to destroy any self-esteem I had left. Whatever possessed me to hang around such a self-absorbed, cruel man still haunts me. I knew what kind of person he was three months into the relationship, yet I stayed. That was 15 years ago; I never dated again. I'm grateful my adult children were kept in the dark about my foolishness. You can make terrible mistakes at any age."

An older woman is sitting in an armchair, looking pensive
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What's a mistake you made in your 30s or beyond that you regret? Do you ever look back on a decision you made and wonder what was going through your head at the time? Let me know in the comments, or you can submit your story anonymously using this form.