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Millennials nearing 40s reveal 25 mistakes they made that they now regret

Millennials have witnessed a sea change in life ranging from jobs, dating, relationships, the internet and more.

Millennials nearing 40s reveal 25 mistakes they made that they now regret
Senior father and adult son having a good time, Japan - stock photo/Getty Images

Editor's note: This article was originally published on March 22, 2023. It has since been updated.

We spend a good portion of our lives trying to make sense of it. Growing up, I assume adults had life figured out until I became an adult myself. While I scrambled to stand on my feet, I realized not many really have a handle on life. Millennials have had it rough with the steep rise in living costs. While many boomers often accuse millennials of being spendthrifts and not saving money, the truth is that the costs of living have far eclipsed the increase in wages, which is again undercut by inflation, according to Business Insider. It isn't just wages. Life itself has undergone a sea change over the past two decades. Health issues, dating, climate change, financial insecurity ... you name it. Life has become a challenge. One Reddit user asked millennials, those born between 1981 and 1996, what mistakes they made in life and it sparked a whole range of responses. "Millennials of Reddit now nearing your 40s, what were your biggest mistakes at this point in life?" read the post, which received more than 26,000 upvotes and sparked a flurry of comments.

Here are some of the top replies we came across:

1. Hearing issues

Not taking care of my hearing, not even 35, and going deaf. u/Kusanagi8811

Man listening/Getty Images

2. Unhealthy

Not getting healthy earlier. u/Zombiearchivist

3. Not leaving my job

Staying too long at a job in my 20s, just because it was safe and easy. When I finally got the motivation to leave, ended up with an almost 50% pay boost. u/Hrekires


4. Not prioritizing myself

Thinking that I could and should put myself on the back burner for anything and anyone else. u/lenalily227 

5. Accepting myself

I turned 40 this year and just started liking who I am. Why the f*ck did it take 40 years for self-acceptance? u/guscalle

Hiker rest on the edge of a high cliff with sunset views of the city and the sea - stock photo/Getty Images

I've recently noticed this as well. Part of it feels like I've run out of f*cks to give to what others think of me. Dropping out of most social media apps was a substaintial help and really the understanding that most people can't think beyond themselves has been even more impactful. u/Haunthaunt

6. Taking care of my back

Take care of your back. Lift with your knees. Sure it's rad when you grab a fridge by yourself and lift it in the back of a moving truck unaided, but one day that shit is going to have consequences that won't just magically go away by resting and 'taking it easy' for a week. u/Guytallman

Young woman having back pain while sitting on desk - stock photo/Getty Images

7. Spend more time with my Dad

I wish I spent more time with my dad when I had the chance u/CharlieCooper.

Senior father and adult son having a good time, Japan - stock photo/Getty Images

Lost my Dad last year after a 2 yr fight with cancer. When we got news cancer came back and spread significantly, I should have quit my job and just spent all the time I could with him. He was gone in 6 weeks and spent those last 2 weeks in the hospital. Still working through so much regret and shoulda, coulda, and would haves. u/Haunthaunt

8. Not saving enough for retirement

Not saving enough for retirement and not going to college. I have been a stay-at-home mom for 7 years now and have nothing saved for my own retirement. I have a high school degree and cosmetology license but that’s it. If my husband left me I’d be f*cked because I wouldn’t make shit doing hair(when I quit working I was a manager/stylist and only brought in 50k a year plus hours were awful all nights and weekends not great for a family since there are no night or weekend daycares). At this point, I want to go back to school but not sure how to even do it. It’s also expensive and I need someone to watch the kids. I feel stuck. Wish I’d not gone to cosmetology school and instead got a 4-year degree then I could have kept working when I had kids since I’d have a job that could pay for daycare and had better hours! I guess at least my husband bust his ass and makes good money and is saving for retirement but I feel like I should be contributing. u/Poctah

9. Worrying about time running out

I'm not sure if people have experienced the same but when I entered my 30s I became convinced I was rapidly running out of time. Rather than using that as motivation I let it paralyze me with indecision because I "couldn't afford to make the wrong choice." Consequently, I'm now 39 and, though I've had great things happen in my 30s, I regret spending so much time worrying and so little time committing to a course of action. u/tomwaste

10. Experience as much as you can

40 already. Born in 81, so I think I just make the millennial cut. Work to live, don’t live to work. You have half your working life after you turn 40 but only 20-25 years to really live it up before the responsibilities become heavy and your joints start to ache. Live life. Really LIVE it. Experience as much as you can. Every sensation, sight, sound, touch. Be open. Be brave. Live your first few decades in the fast lane. You have the rest of your life to take it easy when you have no choice. u/MrDundee666

Tourist woman choosing Venetian mask on street stall in Italy. Traditional souvenir from Venice - stock photo/Getty Images

I tried to explain to a district manager at Walmart that my job was a "means to an end" and I didn't want to climb the corporate ladder and it just didn't compute. u/expensive_crab_5625

11. Not buying a home

Should have bought a home. We qualified 20 years ago for enough to buy a small 2 bedroom but I didn't think we could afford it. That 2 bedroom would be worth nearly 3Xs and paid off by now. We pay nearly double in rent what our mortgage would have been. Gotta love the SF bay area cost of living. u/Thelazywitch

12. Had gone to uni later

I wish I'd been able to make important decisions — like going to uni — much later in life. It's been nearly 20 years since I left uni and I still haven't used my degree. I didn't go to graduation or pick up the certificate. In fact, I still owe £10 in library fines. u/inthevoidweareone

13. Being depressed

I realized the other day that at 32, I've now been depressed for more than half of my life. Like depression is my default mode. I don't really even remember what was like before. I've given up on the prospect of dating. I can't with a good conscience open up my mess of a life to someone else. Besides, it's hard enough just maintaining the friendships I already have when I'm fatigued most of the day. I wouldn't wish this on my worst enemy. u/MidnightGolan

14. Staying in an unhappy marriage

Staying too long in an unhappy marriage. I lost the last half of my 20s and most of my 30s because of it. u/Zenstation83


Upset young adults flatmates sitting indoors and talking. - stock photo/Getty Images

15. Resolving childhood trauma earlier

I wish I had taken the initiative to resolve my own childhood/developmental trauma much earlier than age 30. I would have had more self-worth in my early relationships, jobs/earning potential, and friendships. u/Broccolimountain

16. Getting married too early

Getting married at 20 and having kids shortly after. A LOT of people warned me that I was starting too young, but I thought I was the exception. I spent my whole life being told by everyone that I was "mature" for my age. So certainly I wouldn't be a statistic! After years of marriage, it collapsed into a horrible divorce, I realized I wasn't the exception. It's not that my love and desires weren't real, they absolutely were! It's not that I couldn't hack the practical day-to-day tasks of family life, I managed that quite well. The problem is that I was not prepared for how much my partner and I would change as humans in our early 20s. Twenty-year-old me had way more in common with the 15-year-old me than the 35 year-old-me. If you are under 24(ish) and thinking about marriage, do yourself a favor and wait another year or two. If this is truly the perfect match for the two of you, then you have nothing to lose — that person will still be there. But if you are wrong, and your underdeveloped brain hasn't caught on quite yet, then you will be grateful you waited just a little bit longer. u/_Diligentstate_

17. Start saving early

If I could tell my 18-year-old self one thing, it would be to save 10% of every paycheck I ever got. u/Putaforkinhim

18. Ask for a raise

Always ask for more pay. Starting, yearly, before leaving, whatever. Get that money. u/sensiblereply

19. Crushing on the wrong person

Pining after the wrong person u/runikepisteme

20. Putting off that trip with my grandad

When I was 12-13 my grandfather and I talked about driving from Florida to Alaska over the summer after I got my driver's license. By the time I got my license (17yo), I was too involved with being with my friends/girlfriend and working. The biggest regret in my life not going on that trip. I’m 37 now and think about it from time to time. u/Thirdstringreddit

Hispanic young woman having back pain while sitting on desk - stock photo/Getty Images

21. Don’t let any symptoms go unchecked

Try not to get cancer. If you feel unwell go to the doctor. I felt numbness in my fingers and toes. Let that go for a few months. It turned to arm pain. Went to the hospital and it turns out I have stage 4 renal carcinoma. Don’t let any symptoms go unchecked. You’re older, and if your body is telling you something is wrong, f*cking listen to it. u/Bakedlawyer

22. Not recognizing red flags in a relationship

Not recognizing early red flags for an abusive relationship. It can be tempting to give yourself over to someone showering you with affection after a long dry spell but pay attention to some important details - how long have they known most of their friends? Are they asking you for money really early on, and for something that seems like they should be able to take care of? Bonus point if one or more of their friends brings up money they owe them too. Do your friends seem to like them? How quickly do they start trying to change things about you or make negative comments? I realized 3 months in that this wasn't a good relationship but stayed for another year just because it was comfortable and I wanted someone to be there, not because it was the right person. Fortunately, I was smart enough not to co-sign on anything. Once the wrong person is living with you it can be extremely difficult and stressful to get them out of your house without risking your own safety, especially if you have pets. It can be tempting to move in together quickly, but it's sometimes not worth the risk. u/Sunshinespectacular

23. Didn't invest in friendships 

I moved a lot as a kid and am what is called a third culture kid. I feel at home nowhere. I learned to see friendships and relationships as transactional and didn't maintain them or invest in them. My early life experience is different from those of stable childhoods and as a result, I am also really closed off. I have learned to assume I have relatively little in common with others, and no longer bother to even try. I have effectively become a hermit, am largely friendless, and ended up sacrificing any chance of happiness to take care of an elderly relative. It is probably too late for me. u/Reddit

I'm a first-generation immigrant that moved around too. I feel like I really relate to how you feel. It's not too late. Join random meetups and pick up random hobbies to hang out with strangers. Realize that to some extent feeling closed off from others is a personal bias and just get practice putting yourself out there. Also, knowing how to casually hang out with strangers is a skill that will get easier with more practice. Anyways, it's never too late. u/ughcantsleep 

24. Should have worn sunscreen more

Not wearing sunscreen. u/bluebxredness


Young man put cream on his face in the morning - stock photo/Getty Images

25. Hold onto your college friends

When you get out of college, keep your friends. No matter how hard it is. Hold on to them. u/mpssss22


A young couple lovingly embrace each other during a meetup/Getty Images

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