The End of Failure

Failure was the only option. Thank goodness.

My life is one big failure. No listen, I promise this ends with a cliché/tongue-in-cheek statement about how failure is actually winning.

But, really. I have always felt like a failure. You’ll fight me on this I’m sure. Just like all my friends have. They start listing things. So I try to list things. In my weakened hours I do the rote gestures, the stations of the cross. And just now, I started listing.

What about Duke? What about…

For the hundredth time, I couldn’t think past Duke, because sometimes I think of getting into Duke as my only success. Or rather, my last success. When I was a kid, the only purpose of anything was to get into an elite university. My parents both went to state schools and they made it their mission to send me to one of the schools they could brag about to their friends. My entire childhood was swept away in SAT prep, sports practices, and academic summer programs my mom picked out for me.

When I got to Duke I was so miserably unhappy. I’m reading a woo woo book right now called The How: Notes on the Great Work of Meeting Yourself and the author, Yrsa Daley-Ward, rephrases the classic “it’s about the journey, not the destination” in a way that finally clicked with me. She speaks more to the idea that if you are not enjoying the process, you aren’t going to enjoy the reward. It’s been a good mantra for me as I dive back into a writing-centered life. But I think it’s been stirring some long-held beliefs I have had about what it means to be successful.

Duke was a let down because the process of getting there cost me too much. The things that I’m really good at are chronically undervalued by most of our major institutions. I had what people at Duke unironically called “soft skills.” And they didn’t mean it in the way followers of Yoni might say it. They meant it to mean weak.

But soft skills were so much a part of who I was. Humor, cooperation, nurturing, these are all me. But if they made me less successful than my peers, then perhaps I was actually just a failure. And that’s what my narrative has been for more than a decade.

As I noted in a previous post, I have been failing a lot lately. Most notably, I was fired from a job that earned me a lot of social clout. Less notably, I have been bombing on stage a lot.

But in this year, the year of our lord Taylor Swift 2013 + 9, I have been failing more spectacularly and beautifully than ever and I have been doing it on purpose.

At the start of 2023, I was coming out of a very intense depressive episode. It was the furthest I’ve ever gone into what my good friend Ocean

might call the deep dark woods, and I think I came out with a vengeance.

I told my therapists (the many) that I was tired of holding myself back. “I don’t want to do that anymore,” came out of everything good and everything bad in me—I was fearful that I might never learn how to let go of my worst quality, self-doubt. But there must have been, somewhere, a bit of hope that it could be done.

What ensued was objectively the hardest year and a half of my entire life. It started with a student ending their life on campus, and ended with me getting fired from an elite college preparatory for insisting that we not turn a blind eye to Israel’s despicable genocidal war on Palestine.

But through these last eighteen months I have been beyond fortunate to have gained, possibly for the first time, a sense of self that is grounded in something profoundly true.

When people ask me about my history with gender dysphoria, I am often at a loss for words. I never thought to myself, “I’m a boy dressed as a girl.” I never once thought, “I’m a boy.” But I did align myself with boys in just about every possible way until I was in high school, when I decided I wanted to fit in. I watched what girls did and I … did that too. Even when I thought I was the most successful girl (aka, the popular girls liked me), I often felt like I was watching myself do things, rather than being present. I was what people told me I was.

Recently, my therapist has been talking to me about dissociation. I never thought I did that. I always thought I was hyper present. But I was actually being hyper vigilant. Because I was never quite comfortable physically, my brain was constantly moving to try and figure out what needed fixing.

When I got home from top surgery, I tried to take myself in visually. But I couldn’t. I would look at my head, then I would look the chest in front of me, but my head was NOT connected to the chest, somehow.

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I’ve been documenting myself post surgery. This was the first video I recorded when I needed someone to validate the fact that I was grieving. I couldn’t find what I needed so I gave it to myself.

And when I forced myself to look right at myself, to take myself in, I started to cry. And they weren’t happy tears. They were tears that grieved for the person I was going to have say goodbye to. She wasn’t my favorite person ever. I found her really annoying at times. I watched her do things I would never do, like suck up to popular girls, put on eye liner, kiss boys. It was never a good look it was always gross. It felt gross.

Even so, she was my companion for just about three decades. But now she must die. And a slow and painful death it continues to be.

Yet, even as this year as tested me in the most Homeric of ways, I have cradled the most sensitive and important parts of me. And in their name, I started doing things I always wished I was brave enough to do: I stood up to bullies, vocally and loudly; I advocated for myself, my talents, and my gifts; I followed through on top surgery; I stated my needs plainly even in the face of forces that had strategically undervalued me. And I dove hard into a dream I have had since I was 17, which was to be a stand up comedian.

And, people, it has not been fun. It hasn’t. And I’m not saying that like a sad Eeyore. I’m saying that I have never had to fight so hard for myself and I am doing so much better than I ever could have imagined. Oh there’s been pain. In fact, it feels like I’ve been feeling pain for the first time. I have sobbed in a way I simply haven’t since I was a teenager. I have allowed myself to feel excluded and disappointed and angry and sad and lonely for what feels like the first time.

But I have also been feeling love and pride and comfort and gratitude.

I have been falling hard in love with the person I have been showing up as lately and it’s probably because they are the person I always wanted to be down to my core.

And of course, the failure that struck my deepest wounds was a relationship that came to an end. But I have been fine. Oh sad, no doubt. But in every other break up I have come out of it thinking I was a failure. But here I am, knowing very well that I wasn’t. I showed up in beautiful, admirable, open-minded, steady, and authentic ways.

In the aftermath, I have been so kind in giving myself exactly what I know I need to keep my truest self protected from harm. And I’ve been open to receiving the greater kindnesses that have come from the hearts of my ever-generous friends.

So I know, even in the face of the great and terribles, I have succeeded in the task I set out for myself last January. I haven’t held myself back. I haven’t held back. I have been the most honest version of myself. These successes have felt real for me because they have been victories within my own values. I have pissed people off, I have stared people down, I have held people accountable,¹ and I’ve gotten my ass back on stage where I belong.

If I have failed to become the person people told me I should be, then thank the dear lord that I dodged such a bullet.

1. Well, I have presented to many folks what accountability could look like, but they were not able to meet me there.