16 Older People Share The Biggest Mistakes They Made When They Were Young

Life’s full of choices, and some of them—well, they come back to haunt you in the most unexpected ways.

Older people on Reddit have been sharing their biggest youthful mistakes, and these stories are a mix of relatable regrets, life lessons, and a bit of the “I should’ve known better” variety.

From staying in toxic relationships to ignoring good advice (or following the wrong kind), it’s a reminder that even the most successful lives come with their fair share of “oops” moments.

Whether you’re here for the wisdom or just to chuckle at some hindsight honesty, these stories might make you reflect on your own path—or at least feel a little less alone about that one decision you’d rather forget.

Keep going for some hard-earned wisdom.

1.

I would say marrying my first husband and marrying my second husband should be the top two, but if I hadn’t married them, I wouldn’t have ended up in California, where I met my now-husband. We’ve been happily married for almost 40 years. The truth is that the bad choices often put us on a path that will lead to the best choices.

2.

Looking back, some of the worst decisions I made were staying in toxic relationships for too long, ignoring my mental health until it became overwhelming, and not taking risks when I had the chance to pursue my passions. Each of those choices shifted my path in ways I regret, but they also taught me valuable lessons about self-respect and growth.

3.

Not leaving an emotionally abusive partner before we had children. Not having at least one more child (I wanted three or four, but only had two). Not recognizing how beautiful I was when I was young, but instead allowing my self-consciousness to intimidate me internally.

4.

Trying to win my father’s approval. Breaking Beth McConnell’s heart at summer camp. That first line of crystal meth.

5.

Quit my job, bought a van, drove around the US, and spent all my retirement money ($33K). I did the math. It would be about $450K by now. Got married in Vegas to a guy I’d known for about two months. (Divorced two years later!) Sold my first condo. Bought for $80K, would be worth $400K now, and paid off.

6.

Taking drugs in my early teenage years. Not making an effort in school. Having a relationship with a person who was an alcoholic for several years, who I knew from the beginning, was bad news. Everything eventually worked out, but I sure went through some hellish years.

7.

I went to live in Europe for almost two years instead of going to university. (I was short on one credit and would have had to make that up first.) When I returned to my parents’ semi-rural home, my friends had all moved on. I couldn’t get a job — my European experience counted for nothing. I was hired by a huge national company that would have allowed me a lot of upward promotions and a great pension. I turned it down because my SO hated them and spent the whole weekend before I was supposed to start railing against big corporations. I should have left then, but I didn’t. Staying with my SO during years of alcoholism, fearing a breakup of the family, figuring I could manage it, and trying to maintain their dignity when they had none.

8.

Choosing the wrong university (should’ve gone to a state school). Not ‘reading the signs’ that my ex-fiance was cheating from day one. Listening to the doctors who told me I couldn’t get my tubes tied at 20 because I’d ‘change my mind’ (I’d known since I was five that I never wanted kids).

9.

Listening to dentists who wanted to ‘save the tooth.’ Spent far too much money and wrecked my health with cracked, infected teeth that just ended up being pulled regardless of what measures they tried. Needed to put my children’s well-being above being a dutiful daughter. My narcissistic parents weren’t any better at being responsible grandparents. Letting anxiety take over, needed to just chill out and not make an already difficult situation worse.

10.

Being more concerned with what other people thought than what I wanted. Not questioning being diagnosed with anxiety and heavily medicated for years. I didn’t get my actual diagnosis until my 50s. My first marriage. At least I ended it quickly.

11.

Nothing really ended up for the worse, but the worst decision I’ve made: #1 I stopped caring about school in high school. I was on the Stanford/MIT track. Ended up with a great career anyway, but I was just planning for more, that’s all. Due to circumstances, I ended up putting myself through community college while working full time and then finishing out at a great state school after I already had what is still my career decades later. #2 Giving up a dream job in a dream city because I’d have to live an hour away from my boyfriend, and I knew that would end the relationship. In retrospect, if an hour’s commute was a dealbreaker, the relationship sucked. #3 Rob, and everything about him.

12.

1) Quit a community college job to raise my first child. Wish I had continued and taken advantage of the tuition discount to get a medical degree. 2) Believing I was fat and ugly at 18. I was a size 8, went to the gym regularly, and had a head of beautiful, long curls, but I wasn’t the skinny ‘blond next door’ model. 3) I allowed my family to ‘borrow’ funds that were not returned. I should have at least invested it in bank CDs.

13.

Not learning about managing money at an early age. Not getting a second opinion about medical diagnoses. Assuming people have the best intentions and common sense.

14.

In November 1989, I was with the West German press corps in Warsaw, and they all tore off to Berlin and said the Berlin Wall was gonna fall. I laughed and stayed put. A few hours later, I watched it all on TV in a shitty Warsaw bar and drank half a bottle of vodka while crying and laughing at the same time. Needless to say, my US newspaper fired me. Buying an apartment in Berlin in 1990. Sure, that price would skyrocket. It didn’t. Left Germany for Austria in 1996. Put the apartment on the market, and it sat empty with no callers for two years. Sold it at 30% less than what I paid for it in 1999. Today, it’s worth four times what I paid. Way back in 1968, when I was 18, I started university in the US and was told by my English professor I should be a writer. My family told me that it was stupid and that I should go into advertising, which I did for 18 years and hated it. Finally, I started writing what I wanted to at 36. Bernard Malamud wrote in The Natural: ‘Each of us has two lives. There’s the life we learn with and the life we live with after that.’

15.

#1 Taking loans out of my 401k. #2 Having kids before being financially stable. #3 Believing what others said I was incapable of. #3 hurts the most. I was able to overcome or live with the others. I wanted to be a lawyer. I was one of the kids in my school who was filmed smoking pot on the side of a school. We were all forced into counseling. When I told my guidance counselor I wanted to be a lawyer when it was time to sign up for college, she told me I wasn’t smart enough. I left defeated. I didn’t have parents to talk to, so I believed her. In years since, I have won law cases for myself, my sister, and one friend… with zero training. Always believe in YOU and go for what you want in life no MATTER what!

16.

Context: The future is unwritten. Therefore, mistakes are inevitable. I’d love to talk to all of you ’cause you had the courage to take risks, got the poop kicked out of you, and are still somewhat kickin’. Seriously. Who wants to talk to people who have never made a mistake? They’re boring. Where as you are….

Alex Buscemi

Alex Buscemi

Writer. Billionaire. Astronaut. Compulsive liar.

@whatsupboosh on socials.