A Letter to My 20-Year-Old Self as I Turn 30 [pt. 1]
Thoughts on career pivots, identities, self-worth, and the surprising relief of letting go of a life plan.
I have been writing this letter in little parts over the past decade.
It’s in the margins of my work papers, in the notes section of my phone, in the many, many, many half-finished Moleskin journals I’ve kept along the way. (Unfortunately, this habit never goes away.)
It’s in conversations with friends and family, in moments of reflection, in the quiet spaces between big decisions.
As I stand on the edge of this new decade, I don’t feel the panic I once expected. I feel confidence and assuredness at my place in the world. I feel peace and gratefulness for this chapter of life. But I would have never dreamed things would look and feel the way they do now.
I was talking about this recently — about old dreams and lostness and things working out — with one of my best friends, Emily. We spent our early 20s running around New York City together living a modern version of Sex and the City lives, except without having money and designer clothes, fabulous apartments, or even interesting dating lives.
Emily and I both have dreary, mid-winter birthdays, so most of our previous celebrations involved hefty amounts of Brunello wines and hearty pasta (because what else do you do in January in New York?) When Emily turned 24, she turned up at one of our favorite restaurants, Via Carota, eyes puffy from crying all day. That’s the weirdness of birthdays in your twenties, a weird mix of excitement and anticipation but also grief and dread. Your life isn’t quite how you would imagine it to be and you feel so much pressure to know what’s next.
I remember that night so clearly. We split a bottle of wine (or two), stuffed our faces with overpriced pasta, and debated whether our jobs were worth the stress, whether our latest crushes were worth the heartache — and headache — whether this city was really it or if there was something else waiting for us somewhere else. How frustrating it was to be paying thousands of dollars in rent for a room smaller than our childhood closets, not to mention the problems with mouse infestations, crazy roommates, and terrifying landlords.
Emily called me recently to rehash her feelings around turning 30. The craziest thing of all? She said it was the first birthday in probably a decade that she didn’t cry on her birthday.
Funny enough, I feel the same way. I’ve always had this weird relationship with birthdays — probably something deep down related to my desire for things to be perfect. (Mental note: I should speak to my therapist about this.) But it feels like this pressure to have things neatly figured out. This year is the first time that I don’t really feel that.
What’s behind this shift? Is it a sign of defeat in getting older? Is it an ease and confidence we gain? It feels like a raw acceptance of this is how things are.
A decade later, Emily and I are both in completely different places. She’s now running her father’s funeral home and cemetery in Balch Springs, Texas, which is, as they say, another story for another day.
We both agreed that we wish we could have known how things would turn out because we spent so much time worrying and fretting and agonizing over the directions of our lives.
“I wish I could go back and tell myself to chill out about everything because it’ll end up like this,” I told her. We both laughed because we knew that we were too stubborn to take this advice at the time.
So instead I’m writing the letter I needed back then — the one that might just resonate with anyone still figuring it all out.
Dear 20-Year-Old Me,
You turn 30 this week. Yes, that big, scary, old age number that looms over the heads of every twenty-something like a doomsday clock.
As you sit here now, you think 30 is a finish line—some place where you’re supposed to have it all figured out. But here’s the thing: you won’t. And that’s okay.
I’ll start with some disappointing news:
Hate to break this to you but you never actually move to DC and become a political reporter (and one day, you’ll think the lucky stars for this)
You haven’t saved up a million dollars in the bank yet, and it turns out making financial decisions as an adult is hard. But you’re getting there.
None of your college crushes were “The One” (again, you’ll thank the lucky stars for this)
You still haven’t bought a home or started a family or even found a permanent city to live — but you realize that all of these timelines are made up.
Despite all of this, I can confidently tell you: It’s all going to work out.
I’ll give you a synopsis for starters: You write for a living (yes, really!) but it’s not in the way that you think. You run your own business, you’ve found a wonderful partner (with a funny Scottish accent) and you’re planning a wedding.
And yes you did eventually move to London.
You don’t know the how or why or when of all of it. And you could not possibly comprehend all of the twists and turns your journey will take. But all of this is beside the point.
Right now, and in every decision over the next decade, you can only move forward as if things will work out, because they will.
You’ll have a therapist along the way that lovingly points this out to you. As you sit in paralysis of making the next decision, she’ll ask “Why don’t you trust yourself that everything will work out?” To which you’ll respond, “I’m not actually sure.”
She then references several of these examples below I’ll share with you as proof that at each life stage, things actually did work out. This should give you confidence to move forward in the next chapter without knowing all of the details.
Understand Yourself, and Let That Be Your Guide
The most important work you can do in your twenties is figuring out who you are — what excites you, what drives you, what makes you feel most alive. And trust me: whatever you’re doing right now? It won’t be what you do forever. And that’s a good thing.
Your 20s = trying to figure yourself out and doing your best to just enjoy it while it’s happening.
That is your Great Assignment for this decade, truly.
The more you focus on understanding yourself, the better off you’ll be.
Moving to New York City is your first step. You’ll have to start from scratch — building a friend group, redefining your weekends, figuring out who you are outside of your family and everything you’ve known. And it was hard. It'll strip you down to the essentials — but will teach who you really are.
They say you have to keep relearning the same lessons until you finally know them deep in your bones to be true. Maybe heed some wisdom from your older, wiser self and try to get them on the first time.
You’ll look back at all your journal entries over the past few years and both laugh and cringe at how often you’d give your the same advice: Be grateful for where you are right now, don’t waste a thought on men who don’t value your opinion, and you’ll always, always regret going for vodka-based cocktail — just accept it.
You’ll relearn this lesson when you leave New York in 2022 and spend two years traveling, living at home, becoming a digital nomad, and moving abroad. (P.S. I know you couldn’t fathom living anywhere else, so don’t let what I’m about to tell you scare you off from leaving.)
This chapter will be so much harder than you think it’ll be.
You’ll feel unstable. You’ll feel lost. You’ll go through one identity crisis after another. You’ll keep trying on different lives like different outfits until you feel like you’d found one that fits you best. But it also shows you something you wouldn’t have learned any other way: Who you are doesn’t change, no matter where you are.
I don’t really love the popular phrase “wherever you go, there you are” because it misses a deeper complexity. On the surface, yes, that is absolutely true. Your problems don’t change because you step on a plane, board a train, or cross into a new country’s borders.
But at the same time, that isn’t reason enough not to go. Yes you might be there and have the same realizations — but there is still so much learning to do in the process. (More on that below.)
And once you realize this lesson, you start carrying yourself differently. You stop feeling like the ground is always shifting underneath you. You start walking into rooms, into new conversations, into new spaces, with a sense of assuredness that you didn’t have before.
And the thing is — if you never leave your comfort zone, if you never put yourself in situations where you are forced to really see yourself — you will never get that feeling.
You never get to know, at a core level, that you can handle hard things. That you can start over. That you can rebuild and still be okay, if not better.
Find Alignment, and Let That Be Your North Star
I want to say this in a way that doesn’t come across as too woo-woo, but finding alignment is the best North Star you can chase.
You have this inner compass — a real, tangible sense of what you like and what you don’t like, what feels right and what doesn’t. Like those icky frat parties on a Tuesday night and those jobs that make you want to poke your eyeballs out. Most of your 20s will feel slightly out of alignment. Pay attention to that feeling.
You’ll find yourself in corporate news environments, waking up every day feeling stressed, burnt out, completely drained. Nothing you’re doing is giving you energy. Those feelings are trying to tell you something, like little red lights blaring ‘something isn’t right.’
It’s take losing your job at LinkedIn, losing that last thread of identity tied to a corporate job, for you to finally step back and say:
“I am only going to say yes to the things that feel good.”
And “I am going to say no to the things that don’t — even if that challenges the version of myself I thought I was supposed to be.”
And that will feel terrifying.
Right now, you’d call yourself a news junkie. Places like The Journal, Bloomberg, The New York Times, and Washington Post top your Dream Jobs list. You’ll end up working in jobs at two of these places and realize that your dream list wasn’t all it cracked up to be.
You’ll start taking on freelance opportunities. You’ll try marketing. You’ll try ghostwriting. You’ll work with startups and venture capital firms and big companies and do things you’d never thought you’d do.
And you’ll start filtering every decision through this question:
“Does this feel good?”
Not “Does this look impressive?” Not “Does this make sense on paper?” Not “Does this align with what people expect from me?”
Just: “Does this feel good?”
And once you start following that, everything starts to fall into place.
This is what pushes you to move to London — even though it defies all practical and financial wisdom. But when you get there, the first six months will feel effortless. And that’s how you know you are fully in alignment. Pay attention to this feeling.