Trying In Public

Where does anyone find the audacity?

Dec 22, 2023

I don’t remember when it started being embarrassing to try, but I do remember how it felt to be embarrassed.

As a kid, I was obsessed with MySpace. I would spend hours working on my profile, editing the structure and design of my layouts or finding just the right code to hide my song choice from the world. Working on my MySpace page is one of the earliest memories I have of feeling truly confident in my ability to express myself and solve problems. In other words, it’s where I learned how to be creative.

The only WayBack Machine screenshot I have of my MySpace in 2008

I’m from Cape Coral, Florida, a city that was once number one in the nation in foreclosures. In 2008, 11,000 homes in Cape Coral were lost due to the housing crisis; that’s 1 in 31 households. As children we played in the adjoined yards of duplexes and cast Walmart fishing poles into creeks. When hurricanes came, the winds would sweep up the bricks from abandoned houses and hurl them through neighboring windows.

Rich, to me, meant anyone who didn’t rent. Real wealth looked like owning a $100,000 house with a pool.

Cape Coral is the kind of place where elementary schoolers walk to the bus stop at 5 am with no streetlights. It is Florida country, a spread-out suburban barefoot kind of Southern that never seems to be fully considered. (Randomly and a little depressingly, Harmony Korine’s Spring Breakers probably does the best job I’ve seen at portraying how it felt.)

By high school, it was clear that as teens we were deeply outnumbered—by retirees and also by cops. Every traffic stop turned into a search. Every party led to arrests. There were, and still are, pills everywhere.

Spread out across town and separated by school zones, we found community online based on shared interests and identities. With the help of the Internet, what otherwise might’ve been just a table of oddballs in a single lunchroom could snowball into a city-wide battle of the bands in a church. (It really was always in a church.)

My social life was formed, stratified, and ruled by MySpace. Top 8's were status symbols. Hate pages and Truth Boxes stood in for bathroom walls, digital archives scrawled with cruel inside jokes.

It was 2010, and the scene era was in full spring. Being “MySpace famous” was more interesting than being prom queen.

15-year-old me recognized this and wanted in.

I didn’t have the language for it then, but I felt what Tina Brown in The Vanity Fair Diaries calls “observation greed.” I wanted to belong, yes, but I also wanted to understand.

I saw myself as an outsider—someone who could, with a little effort, definitely manage to get an invite to those parties cool kids at neighboring schools kept posting pictures from.

And so I tried.

People noticed.

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If being good at MySpace is one of my earliest memories of creativity, getting called out for my MySpace is one of my earliest memories of shame. It was the beginning of my adventures in adolescent social climbing. I was over at a boy’s house for the first time—a kid I’d met online, naturally—when his friend dropped by for a visit.

He immediately laid out his assessment of me.

“You’re trying too hard,” he said.

He knew of me already—he’d probably received my MySpace friend request weeks before. His comment made clear what I already knew to be afraid of: That the people I so desperately wanted to like me saw right through my wanting to my desperation. I stank of desire.

A few months later, I’d make my first appearance on the “239 Hate Page,” an anonymous MySpace profile designed to capture town gossip. My photo was uploaded alongside the same short caption: “Trying too hard.”

To me, the message was clear. To the social world I aspired to, my aspiring was obvious. I learned, in those moments, that it was shameful to care and embarrassing to let other people see you try.

It of course feels silly and hopelessly adolescent now, but those early critiques of my personality shaped who I was and how I behaved for a long time.

Even after I made real friends and figured out who I was underneath all of the drinking and mask-wearing I did to be cool, that feeling of being see-through never left me. And it came back in full force when I decided to start a business and try in public again.

My senior year of college, I was driving to a client’s house when I looked down at my lap and saw a text from my then-boyfriend. I don’t remember much about that year, let alone the exact wording, but it was something to the effect of, “Everything about what you do for work is annoying.”

I’d already been freelancing for two years at that point, making part-time job money helping women run Pinterests or make websites or handle office admin. I was an no-brainer hire and got almost every gig I applied for, which happens when you’re good at the Internet while also being 21 with a $12 hourly rate.

Still, I didn’t see the value in what I was doing. I was the only person I knew that got paid for using social media or writing blogs. All of my “colleagues” were online, people on Instagram or Facebook who I’d met by making content about marketing and business. Everyone around me was getting hired at real salaried jobs while I attended Jenna Kutcher webinars and wrote my own checks. My friends from back home had never left.

I guess that’s why believed him when he said that it was weird and embarrassing to be trying so hard, to care so much about drawing attention to my words and ideas. I was primed to believe it, having already done everything I could think of to try and be worthy of his affection and still not receiving it.

As defensive as I felt, his annoyance made sense to me. After all, wasn’t everyone kind of annoyed of me all the time?

Terrified of being so transparent and feeling constantly critically observed, I disappeared into myself. I stopped posting, stopped writing, stopped trying. The energy I’d once invested into journaling or poetry or updating my portfolio was instead invested into drafting 5-paragraph text messages swearing I didn’t go to that party and apologizing for not texting back fast enough when I was in the shower.

Time passed. We broke up, finally. My Dad died.

By 2017, I was a shell of a person just beginning to crawl back toward a living form. Naturally, I did the only thing I know how to do when I need to express or understand or reinvent myself: I started posting stuff on the Internet.

Pretty Decent’s feed in 2017

First it was SZA lyrics. There were a lot of them in my head after CTRL, so I’d hand-letter quotes with felt markers and share the pictures. That rolled into a mood board. It was the Sporty & Rich era, and for years Pretty Decent was basically an Instagram version of a Tumblr. I’d post pictures of Chandler Bing in AND1 tees next to videos of dolphins next to photos from the On The Run II booklet.

I loved it. It felt like a room of my own online, a place to be genuinely myself, a dreamy little magazine I’d made up. I felt good at something again. I wanted it to grow, so I paid bots to troll through the comments of musicians and artists I loved and mindlessly engage with their following.

The page grew into the thousands. I never showed my face.

The whole time, I kept using and improving those same skills I’d developed in college. I got paid to write emails, make websites, produce courses. By 2018, I was living in New York and working full time for myself from home. I made more money than I’d ever seen in my life, and still I saw hardly any value in my work, even less in myself.

I was in what Julia Cameron would call my “shadow artist” phase, an era of doing everything I wanted to do in my own creative career as a service for other people. A more generous reading might be that I was apprenticing.

The truth? I was working up the courage to be seen.

In 2021, I experimented with a podcast just to see how it felt. (Spoiler alert: I didn’t like it. Now I’m here.)

One of the first episodes was titled "Trying In Public." It was an idea I'd been living with for a few years already as I built out The Study and started showing my face online. Back then I was trying to understand the same question I am now:

How do we put ourselves and our work “out there” without knowing what the results will be? Where does anyone find the audacity?

As it turns out, trying in public is easier when you feel safe. That’s still something I struggle with, especially when sharing my more personal writing. It does feel, as Anna Nalick sang, like “these words are my diary screaming out loud.”

It is a vulnerable thing to write candidly, to make a video, to tell the truth knowing other people will hear. I don’t always have the energy for it.

Still, I’m desperate to explore the question. If nothing else, I’m ready to be a case study of what can happen when you fuck around and find out while letting people see.

And I know I’m not alone. When that podcast episode came out, I asked Pretty Decent’s followers how they felt about trying in public. There were a few answers I expected—things like “imposter syndrome,” or “other people seeing me.” Then there was one that broke my heart:

"People thinking I'm naive for thinking I could be successful."

It breaks my heart because I know that fear. Worse maybe than the fear of failure—it’s the fear of the shame, the “cringe,” of even thinking you might have something of value to offer the world.

We’ve been conditioned to be embarrassed not only of trying, but also of simply believing in ourselves.

In writing and talking about this question for so long, I’ve developed some hypotheses about how to make trying in public easier. It starts, I think, with finding a version of "public" that you feel safe in.

For some, trying in public might look like stepping onto stages, going viral, opening galleries, or drawing a large crowd. For others, particularly those who are building up the muscle for the first time, it can and probably will look much simpler.

It’s like the difference between doing karaoke in a booth with your closest friends versus singing out loud on the Metro. For some, the first option might feel way more comfortable. For others, it may feel safer to be your whole self around complete strangers. There's no one right way.

These days, I’m dedicated to creating spaces where creative people feel safe enough to try. I’m writing and researching a lot about the concept, and I’ve started publishing here in an effort to get a book deal. I’m comfortable admitting that to you not because I’m 100% sure all of this will work out, but because I’ve been practicing trying in public long enough that the idea of people seeing me doesn’t bother me so much anymore.

Photo by Steph Asavale

Now you know I had to bring it up: In her song mirrorball, Taylor Swift sings, "I've never been a natural, all I do is try, try, try."

What I love about Taylor (besides the fact that she is also a Sagittarius Sun and Cancer Moon like me) is that she owns her desire.

In songs like mirrorball and The Archer and Mastermind she admits, over and over, that she does absolutely want you to look at her—that she’ll even scheme and plot and strategize how to make it happen. At the same time, she acknowledges the fear: That in looking, by paying attention, you’ll see straight through to the messy and complicated and mistake-prone human underneath.

For those of us raised on cringe YouTube compilations and MySpace Truth Boxes and hours spent crawling cruel anonymous forums, this feels like a brave declaration:

Yes, I am trying, and I know you can see me. Now what?

A previous version of this essay appeared in a September 2022 email newsletter and a December 2021 podcast episode. I would like to keep iterating on it until it makes sense as a chapter in a book about trying. Currently I am looking for an agent. If you are one, know one or have any sage wisdom about how to find one, please email me. <3