The Agony & The Ecstasy of Sheryl Still Single

So. I am in a hotel room that randomly had YouTube on the TV, and for no real reason I decided to rewatch Sheryl Still Single for the first time in a long time. I wanted to look at it with fresh eyes and see things I couldn’t see before.
 
For the billions of people who have no idea what that is, in 2015 I wrote and produced and starred in a web series about a single woman in her 50s.  
 
Watching it again after some time and distance, I still very much love what was created, and I adore my friends’ performances. I cringed at my acting, as I always do, and as a writer who hates everything I write, there were scenes I wish I had written differently and lines I wish I had nixed.
 
But mostly, it brought back happy memories of filming, of creating and collaborating, of birthing this project into the world and feeling a sense of accomplishment and anticipation at how people might react. At the time, I felt it was a big step toward showing the world my comedic sensibilities.
 
My biggest mistake was losing perspective about it.
 
I do that. I create a Thing, and then latch onto the Thing and pin all my hopes and dreams to the Thing. As if THIS time is for real. THIS time, this particular Thing is going to rocket me to the top. It’s going to be the magic word that will open all the doors to success and allow me to return to the iO Chicago and interrupt a Harold commission meeting to have a Julia Roberts-Shopping-in-Pretty-Woman-Big-Mistake-Huge moment.
 
But I’ve learned, over and over again, that the weight of all my hopes and dreams are heavy indeed, so result of these reckless, whirling dervish thoughts are the same: the Thing fails to meet my own absurd expectations and sinks like a stone, unnoticed, into the abyss. 
 
In a single year, Sheryl was rejected by 12 festivals. It has been accepted by zero. 0-12. That fucking sucks. It hurts (in that obnoxious fragile-snowflake-artist kind of hurt that we love to pretend makes us Fascinating and Potent. P.S. I'm Fascinating and Potent.) And it’s embarrassing too on some level, since so many people generously donated to my Indiegogo to support Sheryl and I don’t have any fancy trophies or millions of views or even a write-up or re-post on a single blog to show them it was worth their investment. 
 
After rejection seven or eight, I began to wonder why I even create. My story in the Chicago comedy world has been one filled with quiet rejection, oversight, not being seen, not being understood, not standing up for myself and generally not getting picked for the team. Sheryl was supposed to crack the code. She didn’t, because she’s not a Cold War spy named Oksana.
 
But then around rejection ten or eleven, I realized something: Sheryl didn't need outside approval. Her very existence was a huge success. A gay kid from a conservative family with a father who had a "Clinton Impeached!" newspaper headline pinned to his bulletin board at work had created something that truly expressed who he was, at his core.

Yet. 
 
As soon as Sheryl was finished, I forgot all this and instead created the most outlandish scenarios of success in my head, so outlandish that it fucked up my aspirational compass so much that outlandish success equaled normal success, normal success equaled mild failure, and actual failure equaled a Deep Impact/Armageddon/Death Star mash-up of exploding planets.
 
For example, when Sheryl was released, I immediately imagined entering the New York Television Festival, getting in and winning the whole thing. I had seen it done before, by people I knew, so why not me? And maybe winning the whole thing would lead to a Netflix deal. Okay John, slow down. Maybe it will just lead to a Logo TV deal. Or, okay, discussions with Logo TV where you can pitch other show ideas. SLOW DOWN JOHN. It’ll probably just be TruTV. FUCKING STOP IT JOHN. You’ll win, but you might not get a development deal. Okay, maybe you won’t win the whole thing but you are obviously winning Best Actor and you should write the names of your big donors on a card so you don’t forget to say them in your acceptance speech.
 
Oh wait, what’s that? Sheryl wasn’t accepted in the NYTVF? I’m sorry, I do not comprehend this reality. Clearly I fell into a tear in the fabrics between the multiverses and I need to Scott Bakula my way home to the reality where I already have my Netflix show and several Golden Globes, please and thank you.  
 
In recognizing this pattern of behavior, I was able to see that these rejections weren’t really rejections at all. They were shots in the dark that didn’t hit their target, and the chances of hitting that target were always slim. Creating is always a shot in the dark. There are no guarantees.  
 
I let the joy of creating get away from me and get supplanted by the desperation to succeed. I do that. I hate that I do that
 
Regardless if Sheryl is 0-12 with getting into festivals or 0-900, the fact remains I created something I’m proud of. Amazing people supported my effort, financially and by lending their enormous talents. I proved to myself and to others I can create something unique and weird and professionally produced. And I learned a fuck-ton. Whatever I create next will have Sheryl’s DNA and wisdom collected from her creation. So in a sense, Sheryl will be a little bit responsible for any success I have in the future.   
 
Because that’s truly why artists create. As practice for the next thing they create.
 
And believe you me, I have been busy creating. There’s much, much, much more to come. Soon, in fact. I’m excited about it. And what’s to come wouldn’t exist if Sheryl hadn’t come first, which means despite my desire to be a Constant Insufferable Sad Fuck and whining about how overlooked she is, it turns out…she was a huge success all along.