Talking to My 20-Year-Old Self

When I was much younger –20 years old– I remember being full of excitement…happy to be an almost-grown woman of legal age and jazzed about all that this meant to me:  I could drink…legally.  I would be an adult so didn’t have to listen to and do what other people told me (something I was never good at).  I would be graduating from college soon and ready to tackle my new career.  I was propelling myself forward on a real live grown-up life!  I’m sure I didn’t really know what all this meant, but I couldn’t wait.

But if I remember correctly, I was also unsure of so many things.  Like how would I find a job I really wanted?  Not just a job, but one that I really wanted.  And, I didn’t want to marry the guy I was dating, but I really dug him;  I went to college and he didn’t, and he was happy with his working-class salary and I wanted more.  How would we figure this out?   I was socially awkward (still am, at times) and I was always annoying somebody…not only was it usually unintentional, most of the time I wasn’t even aware.  What to do about that?  My friends and I were all going in different directions.  Could we maintain the friendship?  Would I make new friends?  How?  I was always full of questions about the “rules of society”: marriage? kids? dress rules? social decorum? How to decide what really matters?

I was excited and full of angst at the same time.  When I think about the way my life has turned out vs the concerns I had then, I want to go back into time and tell my 20-year-old self to “relax”.  “Everything’s going to be fine” would be too much of a platitude, but “you’ll be fine” would be a true statement.

I would tell myself that I now know that most of the things we worry about don’t turn out to be nearly as bad as we anticipate they will be.

I had no idea that NYC was on the horizon and would become my home and the beginning of a really exciting journey.

I would tell myself to “go ahead and settle into yourself”.  Your personality is what it is.  I wasted so much time trying to hide my shyness and being bad at it because I am who I am.  Everybody’s not going to like you –no matter what.

 I went into therapy in my late 30s; turned my internal life around.  I should have done it 10 years earlier and would have been much more chill.

I’d say that following your heart and doing what feels right for you is usually better than following the generic rules made up by somebody else that I don’t even know.  So…no husband and no kids will be fine.  Not joining a sorority (or any other group) when all around you are doing that will be fine.  Getting a master’s degree from a city college and not a highfalutin’ (expensive) Ivy League school won’t even matter in a few years.  (Well, actually it did matter; I wasn’t stuck with a student loan!)

I’d prime myself for all the fun I would have dating interesting and fun men, traveling around the world, and going from job to job because I’m naturally restless.  (Well, the job-change thing wasn’t necessarily fun, but it wasn’t bad).

 Most importantly I would tell myself to learn what it means to be a good friend and cultivate those skills, don’t spend your energy on toxic people (men or women) because you can’t fix them and they’ll drag you down, and learn to trust your gut; so often what I felt immediately was the right thing to feel…and then I’d talk myself out of it.  I try not to do that now. And you know what, my life is not only really good but it’s way better than I ever imagined it would be.  That would have been good to know at 20.

What about you?  What would you tell your 20-year-old self?  How do you think it would matter?

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19 Responses to Talking to My 20-Year-Old Self

  1. Melinda says:

    My advice to my 20-year-old self would be to love myself, no matter what anyone says. To follow my heart and make wise choices instead of doing things that will only result in more pain. To appreciate the positive in life instead of dwelling on the problems. To surround myself with a better quality of people, instead of people who seek to bring me down.
    To focus more on improving my situation instead of seeking acceptance from those incapable of loving me for who I am. To be my own cheerleader. To see beauty in myself. To learn important skills for independence.

    Yes…I should have told myself all of this when I was young.

  2. topcatdancer says:

    When I was 20, I listened to what everyone else said, and based my actions on that. I sure didn't listen to what I wanted to do, I and probably wouldn't of listened to a 40-something version of myself, either. But, it wouldn't matter anyway, because I wouldn't have wanted a single change in any part of my life, because if there had been, then I wouldn't be the me I am today. Now, though, I have to ask myself, what would my 60-something self come back and say to my 40-something self?

  3. eleanore says:

    @Pooja: Thank you for writing. I love hearing that my ramblings are actually useful to someone. Don't let anyone take away your dreams. With a plan, you can make them happen. Naive? Hardly. More like “smart and bold enough to want more”. Good for you!

  4. Pooja says:

    Ms. Eleanore- I'm soon to be 20, and it was incredible reading this post because all that you were feeling at 20 is exactly what I am feeling right now. Including the marriage and kids part. The free life you seem to be living right now, self employed with a job that takes you around the world and gives you financial individuality? That is exactly what I want for myself when I'm older. It's nice to see that it really is possible, and not just a “young girl's naive ambition” as I have been told many times before. So thank you for writing this post and telling me, well, that I'll be fine!
    ~ P

  5. Anonymous says:

    Great post. I'm 57, been divorced 20 years after a 17 year marriage. It feels perfect.

  6. eleanore says:

    The real question, of course, is whether I would have had the good sense at 20 to take my own advice! 😮

  7. Rhona says:

    i like this. i often have moments of …i wish…and this is pretty spot on.
    i would have told my 20 year old self (i'm in my 30's–booh!) to stop being so conservative. live it up. let go of what people think of you because you cant change their minds. travel with your friends. dont be afraid to travel alone. date lots. let your inhabitions go. seek therapy. hire a life coach.

  8. alison h says:

    love it, gosh that would have been nice to receive a visit around 20 from our future selves. Like the photo 🙂

  9. Darlene says:


    I'm always encouraged by your writings…!! I'm still reminding myself of just some of those things that you mentioned and I'm being taught by life's lessons in some of those areas.!! Kudos to you again!!
    Inspiring words….

  10. Sheila Martin says:

    Having come from an abusive past I've learned no matter who or what they are, if some is giving me warnings about someone who has come into my life I listen.

  11. Janeen_Yvonne says:

    Thank you, it's not easy at this age, but I am so grateful for the older women in my life that can help guide me (especially my mother!). I will relax and definitely settle into who I truly am and nurture the characteristics I feel I should possess as a good person. This was definitely a must read for me. I'm plagued with these thoughts more than I worry about doing well in school (that hasn't proved a major problem just yet). Again, Thank You!

  12. Lin says:

    I would tell myself to be more spontaneous, take more risks, be less serious and be less conventional. Instead of sticking my nose to the grindstone, after school I would have been out socializing, making hay and being a “boy” instead of an adult. My life might have turned out very differently, but from my current vantage point, I don't think it would be all that bad. It certainly would have been more interesting!

  13. shelley says:

    This is awesome El! I have a 23 year old daughter who's a deep thinker, she'll benefit greatly from this post. Thanks a million!!!

  14. I admire your wisdom. I loved your advice. Honestly I think of you as an honest person with life and people around you. I wish you best luck.

  15. Janine says:

    Fantastic post, Eleanore! Love it, and have often wished the same thing.
    It's hard to tell teens/young adults not to sweat the small stuff. I have memories of my friends and I sitting on the beach freaking out if we found one stray hair showing, rushing to the nearest bathroom to remove it. I laugh now about how “fat” I thought I was at 60 kilos.
    I'd advise the 20-year-old me to ditch the chronic dissatisfaction and try focusing on anything and sticking to one thing in life, but unfortunately that never changed!
    I'd believe in myself a lot more. I shunned opportunities that the ballsy girls of today would never pass up. I was also totally unaware of my sexual power, so would hang around with gay boys because it was safer and more fun. Mind you, I live in Sydney, and fag-hagdom is somewhat thrust upon you if you inhabit certain areas.
    But that compulsion to follow the pack is so strong as a teen – it can take a lifetime to stop comparing yourself to others. I'm actually looking forward to the period of “acceptance”, which probably won't happen til I'm 50…

  16. Yok says:

    Great advice! The advice I would give to myself at 20 would be to just relax and enjoy the journey! In most cases whatever seems terrifying to you won't kill you.

  17. Michael Ann says:

    Your last paragraph…that's what I would tell myself. I guess learning it later is better than never learning it huh? I loved this, it was beautiful.

  18. MilanoGirl says:

    That's awesome. Brava!

  19. Stella says:

    eleanore- if only I had your wisdom, I'd tell myself the exact same things you would've at 20. Excellent advice.

    In fact I'm gonna remember your advice for now: Go ahead and (keep) settling into yourself. I think the hard part is still not to look at what everyone else is doing and then compare yourself to them.

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