The Art Of Leaving Your Twenties Behind

Personal Development

I’m not 30 yet, but it feels like I have been for a while. The friends I’d gone to school with for years are finally starting to celebrate the big three-zero, and I’ve always seen us as on the same playing field—when they started second grade, so did I. When they graduated high school, so did I. When they started their careers, so did I. When they turned 30, in some ways, so did I.

So I’m not 30 yet, but I feel like I have it in full authority to say: Leaving my twenties is not what I thought it was going to look like. After years and years and years of anticipating it—even dreading it—my youth left me quietly. There was no heartfelt goodbye, no bomb that left me reeling. One day I was 20, and then suddenly, I was not.

I don’t know if I’m disappointed or not.

* * *

Twenty was different. I was always hyper-aware of the days leading up to it, as if my childhood were ticking away. The melancholy felt heavy, finding ways to weigh down every passing moment. I firmly felt I was a teenager until I officially wasn’t one.

I don’t really remember my 20th birthday, though. I imagine that’s because I spent most of the day depressed and didn’t necessarily feel very celebratory. I don’t remember any party, any gifts. They were probably there, but the memory has been carved out from me, left behind to rot. Just another year in the rearview. Just another milestone to look back on and grieve.

* * *

I’ve been told I look young for my age, which may or may not be a compliment—I’m never really sure. When I told one woman I was 29, she did a double-take. “I would have guessed 21,” she admitted. Months later, I met a psychic who told me, “You’ve got an old soul for someone who looks so much younger than they are.”

I’ve been lucky that, so far, this has been the extent of the misconceptions—people are sometimes surprised, and then they move on. But there’s this strange, persistent anxiety that someday this is going to get me in trouble. I’m not entirely sure how to explain it.

Or maybe I do—sometimes I still think about a professor I had in college who, when someone suggested setting him up on a blind date with a woman in her late thirties (still younger than him, it is important to note), replied disdainfully, “I would never date someone over 25.” At the time, I’d been 22.

When men approach me in public, I always worry: What if they, too, assume I’m younger than I am? Will they be disappointed when they learn the truth? Disgusted? Or, worse, will they be angry? I imagine my professor, always so kind to me when I was a student, wearing that same look of disdain, except this time it would be directed at me.

* * *

I’ve only ever known what it means to be young in a world that values youth. The clothes in almost every trendy store are made with me in mind. Most popular TV shows are targeted toward my demographic. The celebrities of the moment are generally around my age, though admittedly, they seem to be getting younger and younger, at least relative to me. 

I guess I’m afraid of that moment when I realize I’m no longer in that category. When it starts to feel like I’m being left behind by the rest of the world because I’m no longer fresh or fashionable or fuckable. When people are no longer empathetic to my problems or understanding of my mistakes or concerned with my potential. What happens then?

Here’s the thing: I know, deep down, that my worth isn’t contingent on my age. I’m just afraid the rest of the world doesn’t always know that. And as much as I wish I could pretend it doesn’t matter what the rest of the world thinks, the truth is that it’s always going to influence my life, at least to some degree. I live here, within the constructs and constraints of my culture. What am I supposed to do when it no longer makes room for me?

* * *

Almost everyone turns 30, I have to remind myself. The curse of living is aging. There is nothing new or interesting about any of this—it’s a tale as old as time, lived and breathed and, inevitably, survived. I guess it was just easy to pretend it would never happen to me.

* * *

In my early 20s, I was cursed with the ever-persistent, nagging thought that I was running out of time. It felt like living with an expiration date looming in the distance, and no matter how hard I tried to live in the present, I couldn’t stop counting down the days until I finally reached it.

There’s this strange misconception held by 20-somethings that greatness is directly correlated with age—or, more specifically, how young you are when you manage to accomplish something. That probably goes hand-in-hand with our societal obsession with young entrepreneurs, and young actors, and young authors, and young tech moguls. We are in constant awe of anyone who can make it onto a 30 under 30 list, as if there is a timeline to being truly exceptional.

The first half of my 20s felt like a mad dash toward this greatness that I was on the verge of losing—I took on every class I could, every university extracurricular that would fit into my schedule, every internship that would hire me. I graduated summa cum laude with two majors and two minors, was part of two different honors societies, ran three campus organizations, and left college with three separate internships and a fellowship under my belt.

Looking back, even with everything I did, life didn’t go the way I expected it to. I wasn’t immediately given my dream job. I entered the workforce with a lot of experience and still somehow absolutely none, right back at square one. The name I’d made for myself didn’t seem to mean anything to anyone. Sometimes it felt like all the work I’d done before was for nothing.

Stepping back from it all, I think that’s somewhat true—I put a lot of pressure on myself when I was young. I felt like I needed a purpose and it bothered me that I could never seem to figure out how to find one. Sometimes I felt like I didn’t know who I wasn’t if I wasn’t doing absolutely everything, and this lack of identity was existential. It never occurred to me that I was only in my early 20s, that creating a life takes time. It never occurred to me that maybe the purpose was in all of it: in the failure, in the growth, in the learning.

* * *

I’m told I cried when I turned 20. I know for a fact I did when I turned 21. The worst year was 22 when, at the end of the night, the waterworks started and never seemed to want to end and no one knew what to do with me. Then there was 23, and 24, and then eventually 25, when my tears finally dried up and I stopped crying on my birthday for good. I couldn’t tell you why. Maybe I’d just grown tired of giving weight to the small devastation of growing older.

* * *

I’m not sure how society convinced us that our 20s were the best our lives would ever be—our natural peak, if you will. The first person who ever made me challenge that notion was my boss and mentor in Italy. “Your 20s are for working hard and figuring yourself out,” she told me conspiratorially, as if letting me in on some grand secret. “Your 30s are for actually enjoying it.”

I wasn’t sure if I believed her then. I think I might be starting to believe her now, at least to some extent. All the work I put in, though sometimes unnecessary, got me here: I have what I know my younger self would consider a dream job (and what I often do now, too). My first book will be published this year—just not at 25, like I once thought I would. I live in an apartment I love, in a city I used to say I was too good to live in. I’m—dare I say it—happy.

But I don’t feel the urge to join that mad dash toward greatness anymore. I’m not even entirely sure what greatness is supposed to be. I look back at all the ways I used to occupy my time in my early 20s and fight the urge to cringe. All of those things were so important to me once, but now I spend my time in other perhaps less productive ways. I love cooking. I love dinner parties with friends. I love writing on Sunday mornings and reading on Monday evenings. I love traveling and drinking fun cocktails and attending too many concerts. I love thrifting and decorating my apartment. I love meeting strangers, not because I want to network with them, just because I want to get to know them.

I tried the whole “greatness” thing. I worked really hard and I figured myself out. I spent my 20s doing everything I thought I was supposed to do and reaping the few benefits that I could. I tore myself down and treated myself terribly and worked myself to the bone until suddenly I realized I didn’t have to anymore. Did I ever have to? I’m not always sure, but I can’t deny that I ended up somewhere good. And like my mentor promised, now I’m ready to enjoy it. I’m ready to just be happy.

* * *

During my friend’s 30th birthday party this past month, we decided to make a drinking game out of the movie 13 Going On 30. It was my first time watching it while closer to the age of adult Jenna than teenage Jenna, which added a new layer to the storyline that I never considered before. It brought up a plethora of questions among the group, including: 

How does she have enough experience to already be the top editor at a major magazine? 

Why is Matty attracted to a woman who’s literally mentally 13? 

What kind of woman prefers to skip over their entire twenties for their thirties?

It was really that last one that intrigued me. Societally-speaking, women seem to have a sweet spot—too young and there’s not a lot of agency, but too old and suddenly you lose relevance, treated by some like you’re completely invisible. Thirty always seemed to push too closely to the latter to be aspirational.

But that was young Jenna’s dream: to be 30, flirty, and thriving. To keep moving forward and find something better along the way. It was a wish I’d never even considered before, not really.

I’m not sure where it is that we learned to measure our life backwards, paying more attention to the gap between where we are and where we’ve been instead of where we’d like to go next. I’m not sure why all my friends seem equally terrified at the thought of finally reaching 30 and not achieving all the things they want to, as if there still isn’t a chunk of life left to live. I’m not sure why I’ve spent so much time dreading this moment—this party full of people I love celebrating a milestone I always considered cursed.

As the movie credits rolled, I turned to my friend and asked, “Would you rather be 13 or 30?” Before he could respond, I already knew how I would answer the same question. I may not be 30 yet, but I do know this: I’m not very interested in moving backwards anymore, not when it feels like there’s still so much waiting for me up ahead.

Here’s the thing: My twenties held my greatest heartbreaks and greatest triumphs, the years that left me feeling lost and alone and the years that made me finally feel found. It was terrible and wonderful and somehow everything and nothing that I was promised. I would never change a thing. 

But I think I’m ready to leave those years behind, to step into whatever is waiting for me once I pass the threshold into 30. Maybe the next decade will be everything I hope it’ll be, or maybe it’ll be all those drab and mundane things society always told me it’d be, or maybe it’ll just be what life has always promised: a little bit of everything.

And to me, nothing sounds more beautiful.

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