Letters to My Younger Self: The 25-Year-Old Who’s Setting Sail for the First Time

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Three paddles leaned against an old wooden cabinet

“Letters to My Younger Self” is a series focused on wisdom and self-awareness. Just as you write letters to a friend to encourage and uplift them, here is the advice we would go back and tell our younger selves.

Dear 25-year-old me,

Your world is about to turn upside down in the best way possible. Don’t worry. You won’t be alone. Take a deep breath, and read on. 

You’re moving to New York City this week! Newly single, newly sober and with no clue how you’ll land on your own two feet. But you booked that one-way ticket. I’m so proud of you! You’ll never be the same. 

But you booked that one way ticket. I’m so proud of you!

This leap of faith will be a touchstone for you in the years to come, reminding you of the great reward that follows great risk. I know it feels irresponsible, almost selfish, to make this move. However, you’ll learn to see this as an investment—both in yourself and the countless others you’ll meet along the adventure. 

You’re starting to wonder if everything your sister told you about God is true. You’re clutching tightly to the handwritten map of the five boroughs. You’re about to fall in love with the world all over again. 

NYC will romance you. Her architecture, modern and old world, will excite you. Her city-dwellers, children and grownups, will teach you. Her parks, lively and quiet, will inspire you. 

Right now, all you see is the unknown. You’re trying to navigate the uncharted waters of your future, ping-ponging between every emotion. I know you’re afraid that you’ll lose your kindness in the hustle and bustle of city life. With intentionality, you’ll grow rich in compassion, learning to love others as you are loved in community. 

Right now, all you see is the unknown. You’re trying to navigate the uncharted waters of your future.

I know you’re afraid that your creativity will dwindle without drinking and partying. With trust, you’ll become a stronger artist, liberated from the heaviness of addiction. 

I know you’re afraid that you’ll miss your “person” by being single in your mid-20s. With faith, you’ll lean into the freedom of flying solo and find your groove. And you will marry a wonderful man who waited for you, too. 

Yes, it will be challenging, too, as evolving can and should be. Your expectations will be interrupted by the colorful, messy reality of life, again and again. Every belief you swear by will be tested until what is gold remains.

Friendships will change. People will surprise you in the best ways and in the worst ways, too. However, with each relationship, each success, each failure and each risk, you will grow stronger. Trust me, I’m living proof.

Your expectations will be interrupted by the colorful, messy reality of life, again and again.

Here I am, writing this letter on the other side of an adventure you’ll take later on: Marriage. Another exciting, challenging, rewarding voyage into the unknown. Except this time, we’re not alone. Everything you’re doing and feeling now will lead you here. 

A little note on writing letters: your words are powerful. To your great surprise and merriment, you’ll end up in places with people you never thought you’d meet. Write them letters just for joy; expect nothing in return.

But remember: You are not beneath them, nor are you above them. Don’t write, or do anything for that matter, to be seen. Get in the habit of being kind for kindness’ sake. 

A related little note: you are worth investing in. Stop picking up furniture off the street. Stop cutting corners and putting yourself last. I wish we would stop doing that even now. Let people invest in you, too. You are not trash.

You are a daughter. That will take some time to sink in, but let it. Let love sink in. 

Get in the habit of being kind for kindness’ sake. 

From where I’m standing, I can see now that there was no other way forward than to let faith set your course. So lift up your sails and let faith launch you into the great unknown.

Cheering you on,
Your Biggest Fan 

P.S. Keep writing.

How do you feel when you were beginning a new journey or embarking on a new path when you were younger? What advice would you give to your younger self?

Image via Sheri Giblin, Darling Issue No. 13

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