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I Achieved Everything My Uncool Teen Self Had Ever Wanted. So Why Do I Feel So Empty?

My perfectionist, type-A self doesn’t know how to process this feeling, and I think that’s the crux of my problem

I have never settled for mediocrity. In second grade, our class tracked the number of books we read each month by moving construction paper figurines around a track drawn on a bulletin board — by the end of the month, I had usually lapped the class. While on the swim team in middle school, I diligently approached my coaches before each race for advice on how to swim it in the best possible way — and then I won. In high school, I never relinquished my first-chair spot in band or my 4.0 GPA.

None of these things came easily to me. I wasn’t a gifted musician or athlete, and I poured hours into my schoolwork, practice sessions, and competitions. I was pretty stressed out most of the time. But I knew that if I worked hard enough, near-perfection was attainable. And attain it I did.

Maybe because of those hours I spent in the pool, in the practice room, or alone in my room with my homework, I never considered myself to be well liked. I was always keenly aware of the divide between myself and the “cool kids." I longed for the effortless way they seemed to make friends, their endless playdates (and, later, basement parties), the certainty with which they interacted with others. Growing up, I always dreaded summers because I grew panicked that I would become isolated from the friends I had made. I continued to rack up awards and accomplishments, but I never felt good enough. More accurately, I never felt cool enough.

My drive for perfection came with me to college, although this time I had a different target. I never would have acknowledged it, but during freshman year I began a dogged campaign to become one of the “cool kids.” As with my first-chair spot or lead in the second-grade book-reading competition, I knew I could get there if I worked hard enough.

It took me four years, but I did it. That girl with the beanie and red lipstick slouching in the back of the room? That’s me now. Want to go to a party? I know three happening this weekend. Feel like checking out an under-the-radar restaurant that serves locally grown food? Talk to me, because I have a literal list titled “COOL PLACES MINNEAPOLIS” saved on my iPhone. And somehow, I ended up with the kind of friends my high school self longed for — the type of people whose home feels like my own and who make me laugh harder than anything. I should be happy, right?

Last week, I was at one of those cool parties. It was an album-release show for a local band whose members had graduated from my university. I knew all of them, and couldn’t make it to one end of the room without greeting at least five people. “You know everyone here,” my friend whispered to me. But as I looked down at the drink in my hand, I was suddenly overwhelmed with loneliness.

I had achieved everything my uncool high school self had ever wanted. So why did I feel so empty?

There are think pieces upon think pieces written about millennials, most touching on “FOMO" — the “fear of missing out.” FOMO was certainly what motivated my quest for coolness, but I don’t experience that now. My high school self would probably have FOMO about my current life! Instead, I feel a sense of restlessness and ennui that frightens me. When I think about the quickly approaching date of my college graduation — a.k.a. the moment when I’m expected to have an idea of what my life will be like in the “real” world — that empty, directionless feeling seems to swallow me whole.

My perfectionist, type-A self doesn’t know how to process this feeling, and I think that’s the crux of my problem. I can’t become content by trying harder. I’ll never be able to create an iPhone list of “WAYS TO FEEL FULFILLED.” I can know every single person at a party, but not one of them will be able to tell me how to fill the emptiness inside me.

One thing this emptiness has unearthed, however, is a better understanding of what led me to idolize the “cool kids” in the first place. It wasn’t a tight-knit circle of friends I desired, but rather the ease with which the cool kids accepted themselves and were therefore able to accept others. For an overachieving try-hard like me, ease was the ultimate goal. I don’t regret the effort it took to form and maintain the friendships and social status I have now. But it makes perfect sense that something I had to chase so hard — something I felt that I was “missing out” on — would always be too slippery to leave me with lasting happiness.

What if satisfaction comes not from aggressively pursuing a goal or seeking to alleviate FOMO but from learning to accept and embrace what’s in front of you right now? That always used to seem like a cop-out for me, just another way to allow mediocrity. But by constantly looking to change my situation into the absolute coolest version, I moved so far away from the ease of simply existing that I can’t recognize how to do so without trying.

But now, with 12 more weeks of college left, I’m done trying to be cool. I’m done trying to be at the best parties, or worrying about getting the most prestigious job. Instead, I’m going to try ... to not try. My emptiness will be resolved with relative ease — I just have to allow it to happen.

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