I’m grateful my adult children never knew about my foolishness. You can make terrible mistakes at any age.

We’re not perfect just because we hit a certain age. Even in our 30s and beyond, we sometimes make mistakes that make us think, “I should have known better.”

Recently on Reddit, user u/otherworldly_mirror asked people to share regrettable mistakes they made after turning 30. The responses show that we’re all still learning, no matter our age.

Here are some examples of mistakes Reddit users admitted they couldn’t believe they were capable of in their 30s and up:

1. Financial Regrets: Taking Out Loans Too Late

Getting an education is valuable at any age. But taking out student loans later in life can lead to long-term financial stress. As one Reddit user shared:

“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.”


2. Romantic Mistakes: Trying to Change Someone

We’ve all been tempted to date someone with flaws, hoping they’ll transform into an ideal partner. But attempting to change others rarely goes well, as one Redditor confessed:

“Believing I could get a guy to change if only I was ‘good enough’ for him. Oof.”


3. Career Consequences of a Long Commute

Many people endure lengthy commutes to keep a job they enjoy. But as one Redditor learned, this can take an untold physical toll over time:

“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.”


4. Workplace Romance Regrets

Office romances may seem exciting, but they often lead to messy complications, as one Redditor confessed:

“Getting involved with a coworker. I was in my 40s. I can confidently say I’ll never, EVER do that again.”

– u/CinCeeMee

5. Ghosting Regrets: Taking the Easy Way Out

When a budding romance fizzles out, it’s tempting to quietly disappear rather than directly end things. But as one Redditor shared, ghosting often leads to guilt:

“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.”


6. The Pitfalls of Blind Loyalty

Remaining loyal to a company for years can often leave us feeling shortchanged, as one Redditor described:

“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.”

– u/beautifulwreck_

7. Prioritizing Work Over Family

Many of us devote tremendous energy to our careers, sometimes at the expense of precious family time. But as one Reddit user wisely noted, we can’t recapture missed moments:

“Throwing myself into work and not being more present for my family. You can’t ever get that time back.”

– u/FineRevolution9264

8. Substance Abuse Derails Life

Some regrettable mistakes can upend entire lives, as one Redditor described about their cocaine addiction:

“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.”

– u/Honest-Register-5151

9. Falling for Fake Friends

They say fool me once, shame on you; fool me twice, shame on me. One Redditor learned this lesson after taking back a toxic friend:

“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.”

– u/jippyzippylippy

10. Cautionary Thoughts on Marriage

While marriage leads to happily-ever-after for some, others end up with regrets, as one Redditor described:

“Getting married. I’ve been happily divorced now for 14 years. I’ll never make that mistake again.”


11. The Cost of Selfish Intimacy

In youth, it’s tempting to pursue fleeting romance without considering others’ feelings. But as we mature, casual flings can morph into cavalier cruelty. One man reflected with regret:

“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.”

– u/PicoRascar

12. Splurging Today, Sacrificing Tomorrow

It’s tempting to indulge in extravagances like flashy new cars. But as one Redditor learned, overspending can jeopardize financial security down the road:

“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.”

– u/pixiedoll339

13. Squandering Career Potential Through Complacency

It’s easy to become comfortable and stagnant at a stable job. But as one Redditor shared, this complacency can stall careers:

“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.”

– u/Joe_Metaphor

14. The Perils of Toxic Friendships

As we age, discernment regarding companions grows crucial – yet some still struggle, as one Redditor described:

“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.”

– u/PeterDuttonsButtWipe

15. Pursuing Passion Over Practicality

When selecting a major, it’s tempting to follow interests rather than income potential. But one Redditor shared regrets about choosing a degree unaligned with financial goals:

“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.”

– u/Iwentforalongwalk

16. Choosing a Lover Over Family

Nothing haunts like forsaking one’s family for fleeting romance. As one regretful Redditor admitted:

“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.”

– u/Senior-Garbage-09_10

17. Finding Oneself Before Finding a Partner

Many rush into marriage without first cultivating a strong sense of self, as one Redditor described:

“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.”

– u/littlemiss2022

18. What to Call It Quits?

In the throes of midlife love, it’s tempting to cling to dysfunctional relationships, despite red flags. One Redditor shared lingering regrets about not leaving sooner:

“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.”

– u/[deleted]

Fellow later-in-lifers, hindsight may arrive too late, but we can still learn from past missteps. I’ll start.

Getting financially entangled with family seemed honorable at the time, but it ended up draining savings I’d worked hard for. Though motivated by love, I learned tough lessons on boundaries and self-preservation that still guide me today.

How about you? What’s a choice you made in your 30s or beyond that you regret with the clarity of hindsight? Do tell! Let’s swap stories so we can all gain wisdom without having to live the mistakes.

I know I’m not alone in looking back at certain chapters and wondering “What was I thinking?” Life is a journey of growth, and the path winds through both peaks and valleys. But sharing candidly helps us navigate future crossroads with insight earned from experience.

The freedom to reflect comes through years of living fully – mistakes and all. We’ve lived, loved, stumbled, and kept going. Now let’s turn back to advise our younger selves…and anyone else looking to avoid similar pitfalls.

I appreciate you all for creating this thoughtful community where judgment takes a backseat to learning. To me, there’s nothing more valuable than peer wisdom in avoiding regrets. We’re in this together!

So please, share your stories and hard-won life lessons below. The comments section awaits your wisdom…

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