My Life in the 90s, in New York City

Hi there,

I was twenty-two years old, working a job I was completely wrong for, in a city that had no interest in waiting for me to figure myself out.

It was the late nineties. New York City. And I was lost and had no idea what I wanted to do with my life.

I was working at a major television media company. The kind of place that sounds impressive at dinner parties and feels, from the inside, like you are slowly disappearing into fluorescent lighting and someone else’s ambition. I spent most of my days in a low-grade existential crisis. Nobody told me it was okay not to know what I wanted. Nobody had said, "Hey, twenty-two is supposed to feel like this, give yourself some time.” What I heard instead, from everything around me, was figure it out. Get on track. Find the thing.

And then one afternoon, John F. Kennedy Jr. walked across the newsroom floor.

He was the most magnetically, unreasonably handsome man I had ever seen in my life. Not handsome in the way that photographs prepare you for. Handsome in the way that stops actual physical movement, that makes the room rearrange itself around a person without the person doing anything to cause it. He moved through that newsroom like someone who had never once in his life questioned whether he belonged in a room. I stood completely still and watched him and had exactly one thought, which was: well. There it is. Proof that certain humans are simply operating at a different resolution than the rest of us.

And then he was gone. And I went back to my desk. And my existential crisis resumed.

But here’s the thing about New York in the nineties, the thing I want you to actually understand if you weren’t there. The city had this energy — a physical, almost electrical hum — that made even the hard parts feel worth it. There were no cell phones, not really, not until the very end of the decade. If you wanted to see your people, you made plans. Real plans, written in the calendar in your head, and you kept them because there was no other way to find each other.

No social media. No curated, filtered, algorithmically optimized presentation of a life. Just actual lives, being actually lived, by actual people with actual faces who had not yet discovered what could be done to those faces with needles and fillers. We wore t-shirts and jeans. We barely wore makeup. We looked like ourselves, which sounds unremarkable, and was, I now understand, a genuine gift.

Photo by Matthew on Unsplash

The clubs were something else. We’d go out and dance until five in the morning. Not to be seen, not to post about it, just because the music was incredible and the night was alive, and that’s what you did. Then walked home through streets that were just beginning to turn pink with morning, talking about everything and nothing, completely alive in the way that you are alive when you are young and in New York and the night has just given you everything it had. The restaurants didn’t require reservations. The parties were everywhere.

I hopped from job to job through most of those years, trying to find something that fit. Nothing did, for a long time. I could not have told you what I was moving toward. If you had told me back then — standing in that newsroom, watching JFK Jr. cross the floor, completely clueless about my future — that I would eventually teach yoga and then build a career helping people understand themselves and their relationships, I genuinely would not have believed you. That wasn’t even in the category of things I could imagine.

And that’s kind of the whole point.

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When Your Life Is Not What You Thought It Would Be

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I know what it feels like to be scared you missed your window. To look around at other people and assume they have it figured out in ways you don’t. To feel like maybe the best parts of your story are already behind you.

They’re not.

The feeling of being stuck - the specific, suffocating certainty that everyone else is moving forward while you are standing still, that the window is closing, that you have somehow already missed the thing you were supposed to be: that feeling is a liar. A convincing one. And completely wrong.

Life moves fast, yes. But it’s also longer than it feels. Long enough for the whole thing to change direction. Long enough to become someone you couldn’t have predicted - the one doing work you’ve never considered, loving people you haven’t met, living in a way that would be unrecognizable to your twenty-two-year-old self.

You haven’t missed your chance. The story isn’t done.

Keep going.

Love,
Jillian

P.S. This week on Jillian on Love, I break down the seven principles that actually keep love alive—from how you talk about your partner to the small daily habits that build connection, intimacy, and trust.

🎙️ Listen on Apple Podcasts