A Letter to My 20-Year-Old Self as I Turn 30 [pt. 2]

Thoughts on career pivots, identities, self-worth, and the surprising relief of letting go of a life plan.

This post is part 2 of a series of things I wish I learned earlier in my 20s. If you’d like to see the first post, you can find it here.

Validate Yourself Internally, Not Externally

This one will take a long time to learn.

As you know, you were voted Most Ambitious in high school, and you wear that label stuck in your head like a brand. It feels like you can never slow down, never stumble, never take a step sideways, never be lost. Because if you weren’t ambitious — if you weren’t achieving — then who were you? (And all the Type A achievers sitting in therapy chairs said “Amen.”)

For years, you’ll chase that validation and learn that it leads to emptiness. You’l climb the corporate ladder, earn those dream jobs, and feel burned out at every step of the way. You’ll feel the most unhappy and insecure you have ever been.

On paper, you had Made It. You have The Job that impresses people. You can say that you worked at The Journal and watch people’s eyes widen. And you loved that reaction. But the truth? It doesn’t mean anything. Those feelings of exhaustion and being out of alignment keep creeping up.

You’ll spend your days in stuffy conference rooms with men in their 60s, dressed in stiff suits, mostly who dismissed your work and ideas. There will be one colleague in particular who clips his toetnails sitting at his desk while on the phone to sources — but again that is another story for another day.

It will take you years to untangle this idea that success has to be something that looks impressive. Now, you’ve built a career in a completely different way — on your own terms. And you’re still successful. You still have a personal brand. You still make a great living. The difference is, you’re doing these things for yourself, not for external validation.

If you take nothing else from this, take this: Check your sources of validation. Ask yourself why you want the things you want. Do you want them because they mean something to you? Or because they signal something to the world?

And the sooner you can learn these things — and pay attention to your gut feelings — the better off you’ll be.

Learn How to Build Something

You need to learn how to build something on your own.

Because eventually, you’ll go on to start your own business. But now, at 20, you can’t even fathom the riskiness and instability of that decision. Why on earth would you not pursue an awesome corporate job?

You’ll get burned more than once — and I’m sorry to tell you this — by companies that don’t actually have your best interest at heart. This comes in the form of unrenewed contracts and lack of promotion and raises. At one point, you’ll get put on a PIP (aka a documented excuse to get fired) and get forced out of a job you thought you love leading to more identity crises (see point above.)

Just a heads up, that job just not a great fit — and you’ll later realize it pushed you in the right direction. But the flashy company and great pay is hard to look past. Remember what I said about validation and learning the same lessons over and over again? This is what I mean.

There is nothing more empowering than realizing you can make your own money — that you don’t need a company to pay you a paycheck, that you can create something valuable on your own.

Once you realize that, you stop feeling powerless.

You’ll learn to see business opportunities everywhere. You’ll do the napkin math on dog-walking businesses, wedding planners, trip coordinators. (P.S. you might want to buy some Nvidia and Apple stock. I can’t explain; just trust me here.) You’ll want to know how people are running things, what’s working, what’s not. And that curiosity will shape so much of what you do now.

You’ll wish more people knew what it felt like to make their first dollar on their own. I wish you could know that feeling right now.

Not because everyone should quit their job — but because knowing that you can is life-changing. It gives you options. It gives you freedom. It gives you security in a way that no company ever could.

And the reality is? The corporate world isn’t stable anymore. It’s not the safety net people think it is. Every company will lay you off the second they need to. So wouldn’t you rather know you can rely on yourself?

The Worst Day (That Wasn’t the End)

You’ll go through a breakup so bad you don’t eat for weeks. He’ll dump you on the same day you lose your job. This will be The Worst Day. Or so it feels at the moment.

And every day after that, you’ll build yourself back, one little piece at a time. This moment serves a little like ground zero and allows you to completely redesign what you want from life. Funny how breakdowns work that way.

Two years from that point, you will barely remember those events—instead, they will feel like a silly fog over your memory. But you’ll look back at pictures from that time and just wish you could give yourself a hug and tell her that she’ll be okay.

What you will remember, of course, are the people who carried you during this time. Your childhood best friend who would sit with you through anxiety spells until they passed. The countless friends who eased your endless worries just by being present.

This feels cliché to say, but as your wise 30-year-old self, I can tell you there actually is some truth in the clichés. Your people are what matter most.

In our 20s, I think it’s so easy to chase novelty and newness because "old" things feel stifling to our growth. And you absolutely should do those things. That goes for relationships too. But in the process of reinventing yourself, don’t lose sight of the roots and relationships that make you you. Those are actually the one source of stability in a world of constant change and chaos

You realize there’s beauty and comfort in familiarity. You’ll eventually find a sweet spot between chasing growth and appreciating sameness — that’s where real contentment lies.

Go explore, learn, grow. But stay attached to your foundation.

Embrace ‘Cringe Mountain’

When you’re in your early 20s, it feels like the worst thing you can do is go against the grain of what other people are doing.

But you know you’ve never been one to just go with the flow with everyone else just for the sake of it. You’ve always gone to the beat of your own drum; lean into this.

What I’ve realized in the past decade is that most forms of putting yourself out there are called cringe. Posting online, trying to build a business, humbly trying to find friends.

The conventional wisdom says don’t appear desperate, don’t draw attention to yourself, etc. etc.

What you’ll realize is that people don’t view it as cringe when you’re on the other side of those efforts. When you’ve built an online audience, or when you’ve gotten investors in your startup or a magazine feature, or when you’ve built this awesome community. We say, wow, that’s so amazing they had this vision and went after it.

I want you to keep this in mind whenever you have the urge to start something or go against the grain. If it feels slightly cringe (but still in alignment with your core self) it might be something worth pursuing.

Create the Community You Want

You have to build the community that you want.

It’s one of the most important things you can do for your well-being, no matter what stage of life you’re in.

You’ll learn this lesson time and time again, starting over in New York, then starting over again when friends left, then starting over again in London.

For a long time, you’ll sit around twiddling my thumbs, thinking, “I wish I had more community.” And then you’ll realize: Oh. That’s on me.

The people who support you, who cheer you on, who understand what you’re trying to do — that’s not something that just happens. You have to find them. You have to reach out. You have to create the space for them in your life.

The first time you build a real community is in New York — the kind where you didn’t have to make plans two weeks in advance, where people just showed up at your apartment with a bottle of wine, where you could sit on someone’s couch and not feel like I had to entertain them. But then, when they left, you have to build it all over again. And again. And again.

But each time, you’ll realize it was possible. And now? You don’t doubt that you can do it anywhere.

Go Where You Feel Called to Go

If you feel a pull toward a place — if you feel like you need to experience it — you need to go. You don’t need to worry about the job, the friends, the logistics. You just need to go.

Because regret weighs more than fear.

This should be your test for every big decision: Would I regret not trying?

That’s why you decide to go to London. That’s why you spend time digital nomading. That’s why you keep choosing the uncertain path over the safe one.

And the hard thing is, you can’t know the lesson before going.

You might go to California and realize you’re too far from your family. You might go abroad and realize convenience and closeness matter more than you thought.

Your priorities will change. But you won’t know that until you try.

And even if a place doesn’t become your forever home, it will still leave a mark on you.

I still have a version of me living this slow, coastal California lifestyle. A version of me in posh, chic European cafés. A version of me bouncing between New York and San Francisco, hustling and building. And even though you can’t live all those lives — at least not at once — they are still part of you.

That’s the beauty of going. You carry those places with you, always.

To a New Decade

I recently did a reflection in a workshop I did with Jenni Gritter. She led us in a meditation where we had to visualize our dream environment, a place where we felt at peace. For me, I envisioned a cozy cottage that had books lining the shelf and a roaring fireplace. A space that felt warm, steady, and deeply mine.

There we had to welcome our future selves to come in, have a cup of tea, and listen to what our future selves had to say. I took note of my future self, appearance, it was polished and put together but casual. Almost like she’d finally leaned into her own signature style. What I took note of most was that there was this ease about her, a quiet confidence.

As if it said — without saying any words — I know my place in the world and I trust it.

Her message to me? It’s all going to work out. Of course it is.

To this day, I still fret and worry about the details and the how behind it all.

Where will we settle and buy a house?

How do we afford this next chapter of life?

How do I build this business that I envision in my head?

How do I make my younger (and future) self proud?

The questions are new, but the answer remains the same. There will always be uncertainty — and it’s okay to trust your gut. It’s got you this far.