Things I Wish I Could Tell My 20 Year Old Self

They say hindsight is 20/20… and they’re right. This gets so so clear once you enter your 30s and you think back to your 20s. “Did I really do that?” “What was I wearing?” and “OMG I can’t believe I ever went out with that person” are questions and thoughts that will fill your head. I know of some things I wish I could tell my 20 year old self that definitely would have helped me out!

So, you may think back to different memories from your 20s and cringe. We all do it. There’s some wisdom you may have wish you learned earlier, too. It really would’ve helped back then, wouldn’t it have?

The First-Hand Accounts of What To Tell My 20 Year Old Self

How do I know we all do it? Because I chatted with fellow 30-somethings to learn the things they wish they could tell their 20-something self. 20-somethings, pay attention and learn from our mistakes. 30-somethings, you’ll probably relate to this hard.

So without further adieu, here are the things that we wish we could tell our 20-year-old selves.

General Advice For My 20 Year Old Self

“‘Stop stressing is probably what I’d go back and say to my 20 year old self. I was too busy stressing about things and worrying about things that honestly don’t even matter anymore in my 30s.

I’d also love to tell my younger self to take more trips and to spend the money while I was still living at home with no bills. Go and have fun, because there will come a day when you have real bills and that’s not as fun…

Oh, and probably the biggest thing – stop worrying about dating. You’ll be reunited with the love of your life in your late 20s and be happily married in your 30s.” – Michelle Ioannou, G30 team

“Being in your 20s is a wonderful, exhilarating time. You have so much potential and so much ahead of you. This is the time to take risks and also the time to think about what you see for your future. Invest in yourself and count on yourself. ” – Nicole Booz, G30 team

“I’d say the biggest two things I would tell my 20 year old self would be to not take for granted the small things that you enjoy – romanticize your life more. It will make the bad days a little less dull. Also don’t be afraid of seeking help for your mental health. It’s the best thing you’ll ever do for yourself.” – Kelly Clark, G30 team

“I really wish I traveled more. I wish I saw more of the world when I was in my 20s. Now I’m in my 30s, married, and have kids and it’s not as easy to pick up and go somewhere anymore. Plus, my travel experience now is very different than it would’ve been when I was in my 20s and single!” – Lydia

Things About Career/Money I Wish I Had Known…

When it comes to career path and money habits, there’s always a lesson learned the hard way. But maybe it doesn’t have to be that way for everyone. Here are a few thoughts these people wish they could tell their 20 year old self.

“Honestly? I wish I took more risks with my career in my 20s. I was very stable at my first job and didn’t even try and strive for more. And, I was happy just getting my paycheck, I didn’t have too many bills, and I was out of the office by 5 most days. But now in my 30s, I have friends with paychecks double mine, who job hopped and worked hard in their 20s and I wish I had done that.” – Chase

“Start investing. I have friends who invested in their 20s and now have much more money to their names than I do. I didn’t think much of the 401K my first job offered and now I wish I had paid more attention to it. That compound interest is no joke!” – Luke
*GenThirty note: if this sounds like you, check out our tips on how to prepare financially for turning 30!

“I was really caught up on getting married by 25 and having kids by 28. That didn’t happen and I really did stress over it in my 20s. Now in my 30s I’m happily married, have an adorable baby girl, and am expecting my second. I couldn’t be happier. And honestly? I’m happy I had my kids in my 30s. I definitely am in a better mental mindset – and financial situation – that I was in my 20s.” – Hannah

All About The Relationship Advice

“I’d tell my younger self to date around more. I was with the same guy in college and then most years after college. We ended up splitting up in my late 20s. Now I’m 30 and feel like I don’t have the same dating experience under my belt as others. Plus, starting over just stinks at this age – I wish I had done this kind of dating game fun in my 20s.” – Andie

“‘It’s all going to be okay.’ Sure, it’s simple, but that’s what I’d tell my 20 year old self. Our 20s are such a decade of change that it feels like everything is a big deal… but it’s not. And you don’t learn that and see it for yourself until you’re in your 30s. I think back to things I used to stress about and want to shake some sense into myself!” – Petrina

“Those aren’t your real friends. It’s harsh, but true. I surrounded myself with the wrong people in my 20s. They weren’t bad people, but they weren’t true friends. But, they were just people who wanted to go out just like you did; they weren’t real people you can count on. You’ll find those real friends in your 30s and the friendships will be much more meaningful!” – Lucy

“I’d tell my younger self to stop dating the bad guys. I honestly thought I could change them. After my fourth breakup, and at 31-years-old, I finally then started realizing that I couldn’t change them and that I should start dating a different kind of guy. Lo and behold, I ended up marrying the good guy at 35-years-old… and I didn’t have to change him!” – Carissa

Final Thoughts On Things I Wish I Could Tell My 20 Year Old Self

It may seem like the “hindsight is 20/20” phrase is too cliche but for these situations it rings so true! For some of us, even those of us still in our twenties, these observations hit way close to home.

Regardless, life is about learning those lessons and sometimes learning them the hard way. It’s all a growing experience and hopefully we can learn these lessons sooner than later.

Is there anything you wish you could tell your 20 year old self? What is it? Leave it in the comments below!

About the Author

Michelle graduated from Fordham University with a Bachelors of Arts ’13 and a Master of Arts ’14. She’s currently working in corporate America with a side of freelance writing. She wants you to learn from her experiences and mistakes so your 20s can be your best decade. When she’s not working, she’s likely planning her escape to a tropical island.