A “Tough Love” Letter to My Twenty-Something Self


Image by Colleen Eversman of 2nd Truth Photography

A lot happened in my twenties. I graduated college. I lived alone. I lost weight once so dramatically I thought I had a ringworm. Turns out, life after college simply means you stop being such a pile of shit. I changed careers. I fell in love with my future husband (eww, I’m so gross!!). I wrote a book. It was…a lot. A lot of good things. And I was equal parts a messy jerk that went along with my life as if it was never going to end. A blessed and doomed dance, it was.

My twenties were all about getting to know myself. What could I handle? What couldn’t I handle? How did it work to be truly alone? How could I become someone I loved and accepted? Why do I keep getting hung up on The Bachelor every time it’s on TV?

Now, I’m in my thirties. I’ve learned how to be grateful. I’ve learned to find ways to love myself alone. I’m not saying I have everything figured out (nobody does!!). However, a decade of self-reflection allowed me to fall in love with another, accomplish some things I was proud of, and move forward with patience. I wish I could have found a washed up message in a bottle with this letter to my younger self. If we’re lucky enough, all of us wish we could have our future speak to our current world; tell us we were going to be fine. So, I hope this letter will make you laugh and give you some light.

Dear twenty-something me,

Are you going to read this entire thing? Probably not. You’ll read the headline and then move on. You don’t have time for anything and I know that. Life is all about what your friends think and who loves you the most and the last guy you loved and all of your goals. I don’t mean to be condescending. I realize you needed to go through those things to get here. Learning how to operate in life is all about the process, all about the mistakes, and all about the lessons that come out of those things. So, here are some things I want you to know:

You’re not going to marry the lacrosse player that doesn’t like you beyond your breast size. You don’t know how incredibly OKAY that is right now.

Stop calling your mother to complain. Call her and ask her how her day has been going.

Enjoy the Chipotle. You’ll get sick of it eventually.

There are going to be so many people in your life you fall exquisitely in love with that you don’t even know exist yet. One of them will be your husband. Two of them will be your niece and nephew. What’s beautiful is, you don’t know how those different forms of love feel yet. I can’t wait for you to have those moments for the first time. You will wonder how you lived without them.

If you think becoming “more understood” comes with age (I know you do), you’re wrong. You will not be taken more seriously when you’re thirty. But your work will feel more confident. Your writing will take shape and you will find your voice. The rest shows up while you make art, love, and tell the truth.

Don’t spend that high school grad party money on UGGS. Oh my god, you did it anyway, didn’t you?

I envy the fear you feel. Fear was naive and safe at twenty-something. When you get older, fear is going to be tangible and teetering as if a cliff is always inevitable. Fear is certain. So, revel in what twenty-something fear gives you. Try it on. Wear it. Use fear to your advantage and find the courage to be brave.

Stop putting your student loans on forbearance.

The first time you try birth control, the estrogen levels are going to be too high and you’re going to feel insane. Talk to your doctor. Don’t drink the tequila.

Stop buying clothes that are too big for you. You’re beautiful.

Building an identity on your achievements is too much to take on. Don’t do that. I’m happy you became a flight attendant when working in an advertising agency wasn’t for you. I’m happy you moved home. I’m happy you didn’t make any money. I’m happy the decisions you made were gutsy and yours.

Some people won’t like you. What a concept!

Easy on the photo editing apps. Your face looks like it’s made of cream.

That thing where you drink a ton of booze and wake up feeling like you have unlimited blessings is not going to last into your thirties. In fact, you might have two IPAs one night and wake up feeling like hell! So, lap it up, love.

You’re going to be an author like you always dreamed of. How ’bout f*cking that?

Every single man that doesn’t text you back, ghosts you after a second date, drunkenly hits on you—you will forget every. Single. One of them.

Your body is incredible. You may not feel that way. You probably think you’re fat and not tan enough and your skin is bad. But honestly, your body is the strongest it will ever be. When you’re thirty, you’re going to go back on Facebook photos from college and envy the perfection of its elasticity and softness. Please, please be grateful for her.

Now that we’re on the subject, put on a bikini and go dance in front of the mirror. YOU’RE WELCOME, HOTTIE.  

You’re not making enough money. You won’t make enough unless you ask for it. And sometimes, you won’t even make enough money then. So, ask for the money. Stand up for what you deserve. An ad agency isn’t going to pay you enough for an entry level position.

Sex gets better.

You are the only one responsible for your happiness. Stop putting this pressure on strange men and your mother and your best friends. It’s about you, not them. Don’t mean to be harsh but this might take you a while to learn!

I’m sorry about your friend. I’m sorry you had a falling out. It won’t matter in a year. She’s moved on. So have you. And it’s for the best.

You are the only one responsible for your happiness. Stop putting this pressure on strange men and your mother and your best friends. It’s about you, not them.

Take the risk, whatever the risk is. You don’t have kids. You don’t have a mortgage. Now is the time.

A work email isn’t as scary as you think. Don’t use so many exclamation points.

None of your tweets will go viral. So, chill out.

Show up for your friends. If they invite you to things and you adore them and they are good to you, showing up is more important than any gift. I know you’re going to make a few mistakes in this department but get them out of your system.

The man you fall in love with is going to love you for all the things you haven’t loved yourself very much for: all of your freckles, your dorky tendencies, your bad taste in food, your big calves, and your kind heart. You deserve this love.

Having a kind heart ISN’T A WEAKNESS.

Read more books. Like Dreyer English, anything Joan Didion or Nora Ephron. Maya Angelou! It will make you a better writer. And if you don’t read these authors now, it will take you three decades to find these magical authors.

Live alone. Don’t have any pets. Live completely, selfishly, and freely for yourself. If just for the duration of a lease.

For some reason, you’ll remember everything that happens up until you’re about twenty-four years old. Then, life will get a little hazy. Write things down and track your life. You’ll thank yourself later.

I know you have a cute little plan up there in your brain. That’s right. You know the one. The one that’s like “kids at 28” and “married by at LEAST 25” and “buy a house before all that.” News flash: you won’t have any of those things by the time you’re thirty and that’s so much more than fine.

Actually, things will turn out better than you ever imagined. Instead of a kid, you’ll have written two books. Instead of being married at 25, you’ll have found the love of your life to patiently wait until you’re ready to get married (without breaking the bank). Instead of a house, maybe you’re really happy in an apartment that’s as much yours as a limb. Be grateful.

This might sound weird, but do a somersault or a cartwheel. Run outside and stretch or teach yourself how to do the splits. Thirty-years-old is by no means an end-all for movement and flexibility. But, I am starting to feel things get slightly harder; I’m more careful. The twenties are for us to be wild and moving.

In response to the above, go take a nap. The twenties are so full of available peace and quiet it makes me sick.

The minute you turn thirty, stop making that sad face when you tell people you’re thirty. Own it, damnit.

BY Brittany Chaffee - June 25, 2019

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June 27, 2019 7:11 am

I loved this so much. Yes, I cried.
Thank You.

June 27, 2019 10:29 am

We are the only responsible for our happiness…so true and so sorry I’ve realised that after thirty…
Thank you, Brittany, great post!


Camelia Dragan
July 1, 2019 3:37 am

I am about to turn 24 in a month and this couldn’t have come at a better time in my life. Almost every word felt like a glove to my life.

Thank you so much for writing this. It helped!

[…] truth is, once I take a great, arduous take a look at a number of the routines (or lack thereof) of my twenties, I lament the truth that I made life a lot tougher for myself. However once you’re residing in […]

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