Things I Wish People Told Me When I Entered My 20s

Here are some things I wish someone told me on my 20th birthday:

Sometimes it will feel good to love the wrong people. Sometimes it will feel good to date someone you won’t remember or someone who won’t remember you. Sometimes it will feel good to not be loved at all. In this case, try to love yourself. Just try.

Some of your friends are poison. Very few will actually have your back. The best friend/roommate you have in college? They might be gone in two years. Gone to Portland, Europe, California, a small vineyard in Rancho Cucamonga. If there wasn’t a huge falling out between you two, they might just slowly start to fade away like an old picture. Games of phone tag will go on for six months until it’s reduced to a catch-up email. “How are you, my old best friend I used to share everything with? Is the weather nice where you are?” This is acceptable for a lot of friendships but with certain ones, you’ll want all or nothing. You’ll want to respond, “Either be in my life completely or not at all because it’s too painful to have you in the in-between.”

Taking care of yourself will be the most difficult job. Harder than your first 9-to-5 or a demeaning, grueling internship. You’ll enter this decade burning the candle at both ends and it will feel damn good. Oh sure, you’ll pretend to shame spiral and feel guilt over your naughty behavior but deep down, it will feel so delightful to test the limits of your life. It’ll feel so good to know that you can go out till 4:30 a.m. and still show up for work five hours later and do an okay job. You can conceal the weariness with a smile and do the bare minimum of work that day. It will feel hellish, you’ll regret how hard you raged the night before and try not to do it again, but a part of you will feel totally satisfied. You did it. You had your 20-something cake and puked it up in the bathroom at work too. Suckers.

When I say “taking care of yourself,” I don’t just mean lights out at 11 and going to a soul cycle class. I’m also referring to your emotional well-being and finding a lifestyle for yourself that feels sustainable. Everyone tries to operate on extremes. Either they’re one phone call away from rehab or they’ve become a total grandma who never goes out. Neither of those two options are realistic though. Neither involve balance, which is what we all ultimately need but have trouble getting. It’s probably the most elusive thing in your 20s. That, and a well-paying job.

It’s possible to think that you’re the best, that you’re owed great things because you’re funny, smart and went to a good college, while also totally hating yourself and wondering what the hell you’re doing all the time. This duality of self-loathing and hubris will be your major tension. It will inform and tear at most of the decisions you make.

You will have moments that will make you feel so exposed and alone. Eating solo star at a restaurant on a Friday night, going to the doctor, walking around aimlessly by yourself at 3 o’clock in the afternoon and deciding to catch a movie, walking home from a bar unattended, taking a long subway ride by yourself, waiting at the airport for someone to pick you up. These things don’t hurt you all the time. On the contrary, they can bring you major contentment. But sometimes, on the wrong day, on the day where you feel like a raw nerve, any of these activities will leave you feeling so small.

Um, this is all depressing advice, so maybe I should end it on an optimistic note. One thing you don’t realize in your 20s is that anything is possible. It sounds trite but it’s true. This is your moment. People like to think that the odds are stacked against them. Crappy job market, no money, no support, no clue how to enter the field you desire. While a lot of this is valid, you have to realize that by being the new generation, it’s our turn now. Someone has to be the new, great filmmaker, artist, scientist, author, etc. So why not let that someone be you? What’s different today than back then is that there is no clear path anymore. Lines are smudged, career trajectories are murky. But that’s also what makes it so exciting, don’t you think? You can create your own journey and become a trailblazer. I mean, is that a ridiculous thing to suggest? I’m typing this out and kind of wanting to gag at the saccharine tone, but I still think it’s true. I still think it’s possible to go after what you want and get it. It just involves a buttload of discipline and tenacity. You also can’t ever second-guess yourself. Imprint it on your brain. You will become who you want to be. There is no other alternative. The power of positive thinking often feels sooooo “delusional sorority girl” but it’s effective in many ways. It certainly can’t hurt, right? Besides, you’ll need all the help you can get during this freaking decade. TC Mark

All information provided in this article is for reference purposes only.

Ryan O'Connell

I'm a brat.


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  • Ara

    This is great! I just entered my 20s and I’m already needing all the help there is while maintaining independence and self-reliance.I do realize that whatever i make of this decade might determine all the rest of my life :)

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  • Jeffrey Pereira

    I needed to hear that. I’m a rising Senior currently in my undergrad and everything is just so uncertain for me right now. I work pretty damn hard but things just don’t work out and somehow, someway, reading this article gives me a little reassurance. Thank you!

  • R

    I’m turning 20 next month. Thank you for telling me all this!

  • Ashley

    Just entered my 20s, so I thank you for this!

  • Leslie

    This article meant so much to. It’s both strange and wonderful to see your thoughts and emotions in someone else’s writing.


    Reblogged this on Olivia O. and commented:
    I can definitely relate.

  • amanda

    It was going so well, until that last paragraph. Ryan, take your writing seriously. If you don’t know how to end an article yet, let it sit for a few days and come back to it instead of throwing some lame conclusion on there.

    The second to last paragraph is perfect. “But sometimes, on the wrong day, on the day where you feel like a raw nerve…” – that’s good writing. Work towards getting there, on honing down ideas instead of tossing tens of articles into the air without a second thought.

    • Matt

      Good criticism

  • Danielle

    I want to be Ryan O’ Connell…

  • Kate

    Ugh. I’m the grandma who never goes out. I hate myself.

    • heythereisabel

      Uh I know what you mean… I’m just like that too

  • theroaringtwentiez

    Reblogged this on theroaringtwentiez and commented:
    Good advice.

  • Haley F (@geology_rocks)

    Being in my late 20’s, I can vouch for the validity of this article.

    Go get em’ tigers!

  • Emily

    Staying up til 4:30 and showing up for work 5 hours later? that is me today, word for word… hence my being on TC instead of accomplishing actual work. LOVED this article!

  • NSC

    It’s been a long time since I read anything from you Ryan, but I liked this quite a bit. I wish there was a way to make 20-something’s feel positive about where they’re at & where they’re (possibly) going to be in the future – but that might be the nature of this period in all of our lives. Self-deprecation, guilt and misery might be what it takes to make it to 30… unless you’re flying into your third decade with a silver spoon in your mouth.

  • Rachel

    “Either be in my life completely or not at all because it’s too painful to have you in the in-between.”
    I said this an old friend of mine over a year ago and at first it was the most painful thing to say. It’s great to hear that this is normal and it’s ok to want all or nothing from some people. We have since cut ties completely but I think it’s for the best. Thanks for writing this.

    • Deanna

      couldn’t agree with this comment more. :)

  • AnnamariaPhilippeaux (@Amphx)

    I’m 19, and scared! But I do spend a lot of time wondering what my twenties will be like and how much potential lies in them. But you’re right, it’s the best time of life to do absolutely anything.

  • Renee

    Thank you.

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  • Aimee Vondrak

    Pretty good stuff here Ryan. I stopped reading TC for a while because it all became really trite and I wasn’t seeing the life truths I was used to, but this one definitely struck a nerve. Well done.

  • Elliott

    What I really need is for someone in their thirties to do an “It Gets Better Video” for us psychically stunted twenty-somethings . . . But this is a very sweet-natured piece, and I hope I can learn to take its advice.

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  • juststartedthinking

    Reblogged this on Just started Thinking's Weblog.

  • juststartedthinking

    I love your posts!

  • P

    True, true. I can totally relate. It’s a solace to know I’m not alone.

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