When being an overachiever is no longer a badge of honor

I’m trying something a little different from my usual practical, strategic business advice, and am sharing one of my most recent pieces I wrote over on Substack! In my publication F*cking Around & (Hopefully) Finding Out, I write about entrepreneurship, curiosity, big dreams, and little joys – I’d love to connect with you over there!

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As I sat down in the middle school counselor’s office at 12 years old, I thought to myself. . . how did I get here?

Not by getting in trouble, or causing problems in the classroom—no, I wasn’t a troublemaker, or a disruptor to my teachers. In fact, I was probably the very definition of a teacher’s pet.

My biggest issue wasn’t skipping classes or turning in my homework late: it was completing every assignment to sheer perfection, staying up late to make sure I showed every ounce of work on my math worksheet and that every word of my social studies essay sounded as if it were written by someone no less than two grades above me.

No, my school troubles lay in the fact that any time I received anything less than an A- on a project, a note of constructive criticism marked in red ink on a language arts paper about an inconsequential novel, or a wrong answer on a science test that I’d worked myself into the ground to study for. . . I broke down sobbing, beating my little 12-year-old self up for being a total and complete disappointment—though only to herself.

It wasn’t a teacher that sent me to the counselor’s office; no, it was my very own father—who just so happened to be my middle school principal at the time. (My dad, the principal, sent his daughter to the counselor’s office!! Nice.)

Except none of the pressure I felt to achieve, to be perfect, came from him or my mom, who only ever told me they wanted me to do my best: it all came from myself. I’d always seen being an “overachiever” and a “perfectionist” as a badge of honor, as a gold medal that increased my value and worth as a human being, and whenever my work didn’t match up to that, it meant I was a failure as a human being.

Why? For what reason?

Where it originated, I’m not sure, but that perfectionism (or whatever annoying trait it is) has continued to show up in many ways as an adult, even though I’ve improved a whole lot since that day in the counselor’s office, when an adult who I admired and respected bluntly told me that it was okay not to be perfect. That it was okay to get a bad grade (though in my eyes, “bad” equated to a B+), to fail a test, to turn in an assignment late. . . the world wouldn’t end, and I wouldn’t immediately be perceived as a disappointment to everyone around me. That actually, the grade I received on a paper in middle school didn’t determine my worth.

Now, at 25, that perfectionism still comes out to play when I decide to start a new hobby, to grab a set of watercolors from the local art supply store—and have to intentionally restrain myself from buying the highest-quality set that everyone on on the internet recommends, because I believe I can’t possibly succeed without it; when I sit down with the cheap tubes of acrylic I just brought home and begin to swipe my brush across the page, only to be disappointed that with my little experience from middle school art class, my minimal supplies, and my lack of years studying the medium, I can’t perfectly execute my vision on my first try.

It shows up when I realize I’d like to try and overcome my lifelong loathing of running, setting out on what should be a simple, easy mile through the neighborhood—only to give up when I can’t immediately, perfectly match the 7-minute mile pace I could reach effortlessly during my middle school years.

Like shit, when did it become such a deeply ingrained belief that to enjoy something—a creative activity, a craft, the learning of a new skill or the practice of a new hobby—I must be the best of the best right off the bat? That to find joy in creating, exploring, following my curiosities, or feel worthy, I’m required to have intrinsic talent; a natural instinct present since birth that guides me and effortlessly transforms me into the next Van Gogh? It’s EXHAUSTING.

Just a few nights ago, I found myself getting incredibly frustrated that, despite having literally zero real experience with acrylic paints, I couldn’t accurately replicate the painting in the YouTube tutorial I was following along with. Every bit of me wanted to stop and give up, and felt like there was something inherently wrong with me for being unable to flawlessly execute the perfect painting right off the bat.

I shared a quick note about this on Substack (mostly for myself, to find some humor in it and see how silly it was), and the responses I got showed me that I’m not the only one who runs into this as an adult:

“I want to pick up a new hobby. But I want to be good at it immediately. Oh wait, I just spelled delusional.”

“Literally me as I purchased a water coloring course. Have I touched the supplies? Nope. Too nervous I’ll be terrible at it.”

“My sketch book and watercolors are sitting in front of me. And have been for months. A former skill and I am afraid I can’t do it again.”

My immediate reaction to seeing these was oh my god, you guys—that is so silly and you should absolutely get your watercolors out and try again!! Who cares if you’re bad at it?!

But would I ever give myself that same permission to try something and fail at it, to enjoy something even if I weren’t objectively “good” at it (at first, or ever)? Hell no.

I mean, I won’t lie: it feels GREAT to be naturally, inherently “good” at something with minimal effort. The applause you get from being a natural artist, creative, singer, musician, athlete, or academic makes you feel like you’ve done something right; like you will always have something to be proud of. It feels like, from your very first breath, you’ve had an intrinsic sense of value and merit worth praising.

And I think we all do have those talents and skills within us to varying degrees—for me, running a business and being in charge of my job comes naturally, and feels like something that I was able to do without much resistance. For others in my close circle of family and friends, this might look like being naturally gifted at teaching, sports, mathematics, writing, or even putting on magic shows for classrooms of young children (looking at you, Baba).

But I’ve realized over the last year or two that the things that feel best to me are the ones I’ve worked hard at to achieve; the ones I’ve had to practice, and the ones that have required me to put my ego & pride aside to accomplish.

Running, for example, is something I would say I’m NOT naturally talented at. Sure, in middle school I could run a killer mile and achieve a pace that would get me that lauded Presidential Fitness award (lol, what was the point of those?), but I was also 100 pounds and not yet weighed down by the pressures of being an actual human adult. When I tried to run for the first time as an adult a few years ago, I immediately realized I couldn’t do that anymore—I was exhausted and out of breath after running for 5 minutes, and absolutely could not fathom myself running farther than a mile.

This past weekend, though? I ran eight miles without stopping. . . and I felt GOOD at the end. EIGHT MILES, a distance I could never, ever have imagined being possible for someone like me, who running didn’t come naturally to. Throughout my running journey I’ve been forced to put my ego aside, build confidence in myself no matter my pace or how fast I was going compared to the person next to me, and practice going slow. And I’m not sure anything has ever boosted my confidence more than seeing this real, concrete progress, and realizing that I’m capable of SO much more than I ever believed!

So that’s why I sit here and wonder on this Monday morning. . . why is it so fucking hard to sit down with a god damn pencil and sketchpad and just doodle for the fun of it? To kick back with a set of cheap acrylics and drag a paintbrush across a piece of (non-high-quality, expensive cold pressed watercolor) paper and simply make a shape? A pattern? Swivel the brush hairs around to see what different textures you can create, how the colors mix together, how much fun it is to just play around?

It feels impossible to me; it makes me feel physically uncomfortable in my body and makes me feel incredibly resistant. . . yet when I’m able to push through that intrinsic need to create something perfect on the first try, that is where I find the joy in it. That’s where I feel the excitement of creating, the curiosity of playing around, the happiness in freely doing whatever the fuck I want without expectations or pressure I’ve put on myself.

I’m not saying it’s easy, but it’s something I’m getting better at slowly and slowly, and even though it’s hard to give myself the permission to do it, I find that writing about it like this reminds me of just how silly it all is! If I can tell some random stranger on Substack to stop fearing imperfection and just get the damn paints out of the cobwebs of their closet & fuck around a little, maybe I’ll be able to do it myself, too 🙂

I’d love to hear if you enjoyed reading this post as a little break from my usual content! If so, you can subscribe to my Substack for free for more just like it 🙂