Musings + Essays

What Would You Tell Your 20-Year-Old Self?

By: Jen Shoop

Last week on Instagram, I asked Magpies to answer the following prompt: “If you could visit with your twenty-year-old self, what would you tell her?”

I was moved by the fact that the loud majority of responses replied:

“Do not worry so much.”

Exactly what I would tell myself at twenty, along with the chaser: “Everything in its own time.”

I spent far too much of my 20s racing to the next thing — graduation, graduate school, engagement, marriage, this job, that job. There were countless pockets of time I whiled away in blithe ignorance of their roundness and ease. I still worry too much, but I think my anxieties hang on the worthwhile these days: the health of my family; the happiness of my children. Still, why did I make myself physically ill with worry earlier this year when I drummed up the courage to let my daughter’s Montessori know we would be transferring her to a Catholic parochial school this fall? I have a profound fear of disappointing others that I cannot move around. I would do well to heed my own advice: Worry less. Everything in its own time.

While about half of the messages ran along similar lines — “worry less; it all turns out OK; you’re not late; it won’t go as planned but it will all turn out fine” — I wanted to share a few of the other messages to our twenty-year-old selves because, well, they are poetry, these missives to women we used to know and still love:

“Do the things you want to do — don’t worry about finding The One.”

“It gets better. You will find life-changing medication!”

“You can kill confidence, but you can’t kill drive. Remember to cheer yourself on.”

“Don’t be scared to be yourself.”

“Be kinder to yourself.”

“You are enough.”

“Strong female friendships will be one of your greatest blessings.”

“Do exactly what you love to do and nothing else.”

“It goes so fast — savor each stage and season.”

“Trust your gut — you have plenty of time.”

“Perfect is a myth. You’re doing great, keep going, it turns out OK.”

“You’re the strongest person I know! Hang in there!”

You will be OK.”

Man, I want to be friends with you all — such beautiful cheerleading.



+This is me, this is not me.

+Would you believe how sentimental I am about my children?

+On recognizing the effort.

+On being happy for friends.

+On balancing friendships.

+It is nice to be needed.

Shopping Break.

+Oo! This top is adorable!

+I must own this dress for summer gatherings.

+I also just added this bag to my cart. $65 with those little cherries?! GAH!

+Gifts for little girls.

+Cutest cooler bucket for a spring party!

+I love these frosted reusable cups for evening walks / hanging out in the cul de sac with neighbors.

+I adore this eyelet mini.

+Major lust list item: a Brent Neale necklace.

+Another great pair of shorts — these are ADORABLE.

+Adorable stationery for brothers.

+Sweetest bedding for a little lady.

+Veronica Beard NAILING the footwear game with these.

+So many of you have loved this striped Gap button-down — I think it might be long enough to work over a bikini this summer!

+Love this bag — looks much more expensive than it is!

+The best tupperware ever.

+Mini had this little diaper set when she was younger in a different color — one of my absolute favorite outfits she’s ever worn.

+Reasonably priced white skirt for summer — layer over a swimsuit or pair with a simple tank. (Under $50!)

+These leaf and ladybug plates are beyond adorable.

+This jacket is a forever piece.

+Love this new console at PB.

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7 thoughts on “What Would You Tell Your 20-Year-Old Self?

  1. My sisters made a video to show me on my wedding day of all of the married women most important to me imparting words of well wishes and advice. One of them said to keep in mind through life’s highs and lows that “nothing is ever as bad as it seems, and nothing is ever as good as it seems.” At first I found this depressing. Nothing is ever as good as it seems!? But after reflecting on it further and thinking about it periodically over the years since, I realized what she meant was that life is never perfect, and every situation is full of complicated nuance. Two feelings that are seemingly at odds with one another can co-exist, and that’s just fine. You can be head over heels for your perfect new baby and also struggle with the sleep deprivation, or miss the simplicity of your old life (for example.)

    I wish I could tell my 20-year old self this, and impart the perspective for her to fully grasp it. Nothing is ever as good as it seems, so it’s up to us to find the joy and light and string it along through the ups and downs. Since I have understood this and allowed myself to let those conflicting feelings co-exist, I have found so much more joy and contentment.

    That was a long one! Thank you for making me think and reflect today.

    1. Oh I love this so much, especially the beautiful way you’ve reinterpreted her words as a nudge to look for the light even in the tough moments. It is so true — especially in parenting I find — that a single moment can contain about four or five separate, often incongruous, sentiments/emotions. It is confusing! Accepting that you can feel multiple ways about one thing is a key, I think, to maturity.


  2. Oh these are all so good!

    The things I would say to my 20-something year old self would be these two things that others with more life experience had said to me at the right time in my life.

    When I was going back and forth on a career decision, my kind older neighbor told me:
    “Trust your intuition/instincts, they will never let you down.”

    At a wedding shower, this advice stood out (which can apply to any woman at any age):
    “Every woman should have 3 things: her own friends, her own hobbies, and her own money.”

    1. I love the emphasis on trusting your intuition. So hard to do when you are younger and doubt yourself more and it feels like every decision will stick with you forever! Going to remind younger ladies of that sagacity…


    2. Love the pithiness of the latter but I do wonder how to square it with being a full time parent. I’m not in that camp but I’ve seen, especially during the pandemic, how dependent the careered spouse — or, the spouse’s career—is on the other spouse not (remuneratively) working. I guess this points to the need for full time parents to be compensated and childcare subsidized, but still worth noting.

      1. That’s such a good point, Claire. It reminds me also of a Magpie reader who is a stay at home mom who commented that she feels sometimes triggered by the prevalent cultural messaging telling her to “take a day off/time off to unwind/explore/sit with yourself” when she finds it absolutely impossible to do that with two young children in her care from 7-7. Her comment and yours make me sensitive to the ways in which a lot of “conventional wisdoms” about work-life balance, strong relationships, career, etc do not fit nicely with women who stay at home. Thanks for building this awareness for me.


    3. Hi Claire and Jen,
      100% agree with both of you… I’m currently a full-time parent too and have been since COVID, and my husband is in an essential industry and has had to work outside of the home during the pandemic while I held down the fort at home. And now that my daughter is back in preschool I’m struggling to even think about restarting my professional life. But the pandemic has also made me think more about mortality and the “what ifs” in light of being dependent on my spouse. This discomfort led me to remember that piece of advice, which I took to heart in my 20s for sure. It is definitely not my situation at the moment, which to be honest feels deeply unsettling for me right now.

      I really appreciate what Claire said about how the spouse’s career is dependent on the other parent being full-time with the child(ren). This perspective challenges the idea of the full-time parent being dependent on the careered spouse, and rightfully so. It reminds me of that line from Reshma Saujani’s Marshall Plan for Moms: “Other countries have social safety nets. America has moms.”

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