7 Biggest Regret People In Their 30s Say They Have

Some of these might shock you. Others are obvious.

upset woman sitting against fence Bricolage / Shutterstock

As someone who’s been at the top and bottom echelons of society, it’s safe to say I hear a lot of people’s confessions. I also see a lot of things most people don’t — or at least, that’s what seems to be the case.

I’ve met people worth tens of millions, and I’ve met homeless people. And a lot of those people are now in their 30s and 40s.

Did you ever wonder what the biggest regrets about their 20s are?


Well, I’ll tell you.

Here are the 7 biggest regrets I hear from people in their 30s:

1. "I regret not trying to chase my own dreams"

Oh, do I hear this one a lot!

I hear it from both wealthy people as well as people stuck in dead-end jobs in their 30s. Oftentimes, it’s from people who hear that I make six figures as a writer and that my husband is a DJ.


I swear, it’s like clockwork. It starts with a sigh and a teeth-grit, "Must be nice…"

And then the confession hits: "I really wish I had followed my dream of being a writer…I have kids/too much student loan debt/a mortgage now."

I’m going to be honest. I have very little sympathy for people who don’t make an effort to chase their own dreams because I had people basically disown me and berate me for making that choice myself.

It’s true that your 20s cement a lot of what you can and cannot do in your career. It’s also true that certain careers are off-limits after your 20s end, including professional sports.

If your career demands youth (such as agency-based fashion modeling), you need to hop on that yesterday. At least that way, you know what would be if you chased it.


If you regret not starting a dream that doesn’t require a super young face or body, why aren’t you doing it now?!

Most dreams do not take a full-time commitment to begin, including writing!

RELATED: The 5 Most Common Life Regrets (As Told By People Who Are Dying)

2. "I regret letting my parents rule my life"

I have met so many people who went to college to get a major their parents picked out for them, despite it making them miserable. Like, we’re talking perennially depressed, eating-disordered, level miserable.

I was that kid.

At times, that weirdly creepy level of parental control goes beyond careers and starts to creep into their kids’ relationships and bedroom choices.


Let me tell you, this is toxic and often signals that a parent is really sick in the head.

I’ve even seen one family where the mother listened to her sons having sex, then talked about it with one of her kids’ girlfriends — only to be shocked when the girlfriend ghosted. To my knowledge, both sons are still under the control of Mother Dearest.

Jeanette McCurdy’s book, I’m Glad My Mom Died, touches on this kind of weird control that parents often exert over kids. Some adults remain completely and utterly under their parents’ thumb, like a puppet pulled by its strings.

I have never met an adult who lived this way and didn’t regret staying under their parents' narcissistic control.


This is especially true once the parents in question die. They’re left with a life they never wanted to live and often are too emotionally stunted to maintain a relationship with anyone else.

Rebel. Don’t be that person as you age. Trust me when I say living for yourself is worth the tears you’ll cry.

3. "I regret wasting my time with my ex"

I mean, yeah. Some people are both a waste of time and a waste of air.

If you needed a wake-up call to stop trying to change a bad partner who doesn’t want you into one who will, take this as your wake-up call.

Most of us have lost money, time, and tears over people who never wanted to be good to us in the first place. The sooner you cut your losses, the less you’ll have to regret by the time you’re 30.


On a similar note, many women I’ve met who are in physically or sexually abusive relationships also tend to regret not pressing charges. The same can be said when it comes to suing financially abusive partners.

There’s nothing wrong with letting people experience the "find out" part of "f*** around and find out."

RELATED: 30 Things To Do In Your 20s To Ensure You Kill It In Your 30s

4. "I regret having kids"

Excuse me while I duck behind a cabinet for a moment.

Are we good? Please don’t shoot the messenger, but I’ve heard this a lot in recent years from both men and women.

While many parents would never want anything to happen to their kids, they often admit they wouldn’t choose this path if they knew what it’d be like. That says a lot about what parents have to deal with these days.


The people who regret it most, from what I’ve seen are as follows:

  • Women who were not told the gory details of what it includes, as well as those who were lied to about having support around them from their partner and family members once the baby was born.
  • People under 20.
  • Men who tried to "trap" a woman with a baby, only to realize what having a baby meant for him.
  • Women who tried to "trap" a man with a baby, only to have the man run away faster than Sonic the Hedgehog on a ring run.
  • People in poverty.
  • Women who were talked into keeping the baby by judgmental family members or church members.
  • Women who almost graduated college but dropped out due to the baby.

Really, think twice before you have a kid.

5. "I regret not partying in my 20s"

Perhaps it’s because of who I am, but I hear this a lot from people who are in their 30s who spent their 20s not partying.

Perhaps it’s FOMO, or perhaps it’s because they were scared that they were going to miss out on a career if they actually did what they wanted to. It’s hard to tell.


However, I get it. I really do.

I think back to the great days and nights I remember, and you know what? Most of them were not in a classroom or a workplace. They also weren’t reading or doing crosswords.

They were on rooftops, surrounded by glowsticks and pills. They were with my friends being suspended from chains on a pulley, or having drunk threesomes. They were running from the cops after a party got raided.

They were when I saw a stripper accidentally break a guy’s nose by slamming her crotch on his face, or when my friend pissed on a bank after almost getting beaten up by a guard.

Those memories are things I would never trade for the world. I genuinely feel bad that people don’t have memories that colorful.


Worse, I feel terrible that they’re often talked out of it by others because "What would others think?!"

A lot of people feel weird going out to a club once they hit the big 3–0. I assure you, there’s nothing weird about it. A ton of my friends are in their 40s and still club it up regularly, and some are even as old as 60. (Yes, they go to burner parties too!)

Admittedly, partying in your teens and 20s is kind of a different feeling. That’s the wildest you’re ever going to be and there’s way less at stake if you come to work hungover.

That doesn’t mean it’s too late to at least start living your life.

6. "I regret going to college"

This is a relatively new regret I’ve been hearing, most often from people who went to college only to get saddled with tens of thousands of dollars in student loans.


Honestly, this is probably more of an economic regret for most people I hear this from today. Most people I knew who went to college in the 90s and plenty who attended in the early 2000s don’t regret it.

By the time 2010 hit, things changed drastically. People are now paying for unforgivable debt, only to go into a workforce where their starting wage is marginally more than what a high school grad could get.

This regret seems to be parroted the most by education majors and medical majors. So, it also could be a workplace environment issue as well.

If you go to college, make sure you want to do this. Nothing’s worse than taking on debt for a degree you didn’t even want.


RELATED: 40 Regret Quotes About Living Life To The Fullest

7. "I regret breaking up with my ex"

It’s interesting. For every five people I meet who regret wasting time on exes, there’s always one who is totally emotionally messed up because they dumped the wrong person and were too immature to realize it.

It usually happens when one partner strays or insists on sowing their "wild oats," only to find that the grass isn’t greener on the other side of the fence. You know the type — where they were genuinely treated well, but they decided to go with the hot, new partner who turned out to be awful.


One guy who I saw this with really messed up. He was a party promoter and his girlfriend was a model. She actually made enough money to afford to buy a place in Brooklyn, which is no easy feat!

Well, he cheated on her with about 12 women…and she walked in on it. Long story short, she’s married and living in a beautiful home on Long Island. He’s currently 37 and stuck with roommates. And yes, every time he gets drunk, he asks for her.

But, I’ve also seen the opposite happen. It was a gorgeous girl who thought she was going to be on MTV and a guy who was just working as a data analyst. She dumped him to be "sexy and single" for her career.

To be honest, I’ve never seen that girl as happy as when she was with him. She regularly dated guys in the rap scene and promoters, but they never quite treated her well. Moreover, she never really had much in common with them, either.


She only recently admitted that she regretted dumping her first boyfriend. That had to hurt.

If you’re in your 20s, think about these regrets and act accordingly.

If I had listened to everyone in my 20s, I’d never have modeled. I also never would have partied. I’d have probably shot myself shortly after graduating from college with a degree in Software Engineering.

I would have been miserable and I’d have died miserably and no one would have cared.

Don’t be that version of me.

I might be an addict, and I might be in debt, but I can honestly say that I’m okay with that. I f***ed around my 20s and found out in a great way.

Every day I wake up, I know I’m living on my own terms.


If you’re just starting out, now would be a good time to remember that you’re living for you. Other peoples’ inconveniences are not your emergency. Live for yourself, and live well.

RELATED: 22 Anonymous People Share What They Regret Most In Life

Ossiana Tepfenhart is a writer whose work has been featured in Yahoo, BRIDES, Your Daily Dish, Newtheory Magazine, and others.