Annie Hamilton On Failing

In collaboration with Urban Outfitters and Dickies, we created a series of stories that feature creative leaders who offer their insight on the “new” work world.

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I decided I wanted to become an actress in the closet of my bedroom in the third apartment in two years we’d lived in as a family in early 2009. I held my knees up in that closet, rocking back and forth. “I want to be an actress,” I told myself. “I want to be the most beautiful and famous actress alive,” — I shook more — “And it’ll take me longer than anyone else to do it.” “We’ve always been late bloomers, it took us longer than anyone else to get a first kiss, so all we have to do is hang in there. Hang in there longer than all the quitters, and it’ll turn out okay.”

Almost 15 years later, I no longer think of myself as an actress. I certainly haven’t become the most beautiful and famous actress alive. (I wonder what Emma Stone said to herself 15 years ago in her closet). I think of myself as a performer and writer, primarily as a writer who is good at performing her own words. I like who I am better than who I dreamed up for myself at 17 years old.

From 18 to 28 years old, I ran around Los Angeles, trying to make my 17 year old dreams come true. I had little to no luck. It wasn’t luck; I’m not a very good actress. I’m a good charmer, a good showman, a good writer, but not an actress. I’m not a Chameleon. I don’t transform. I’m always me.

I wanted to be known. I wanted to be known so badly that I forgot I had something to say. I wanted to be known so badly that it prevented me from figuring out what I’m good at.

Before I learned what I was good at, I had to learn to make money. Over the slow course of those ten dead-end years in LA, I worked a variety of intensely awkward day jobs. I was a telemarketer, a hostess, a manual laborer (canning organic face masks in a garage in Beverly Hills), a nanny, a proofreader, a research assistant, a marijuana promoter - the list goes on. Most of these jobs fired me. I believe day jobs shouldn’t be in the realm of what you want to do. Day jobs should be mindless. Day jobs should allow you to completely focus on your craft outside of work. It’s hard being an assistant to someone successful in your dream field. You’re so close, and also…so far (I learned this the hard way).

I have only one piece of advice in figuring this out: put yourself out there as much as you can. Put yourself out there even when you’re unsure of your work because that way, you can fail. The more you put yourself out there, the faster you will fail, the faster the weeds will be weeded through. Failing is a crucial part of how I learned what I was good at.

I learned that I was a writer by accident. I had always written, primarily as an author of many nonsensical tweets, but I considered it a hobby. Something silly that I thought was fun but not something I actually wanted to pursue. Over the ten years I lived in Los Angeles, I posted a lot on the internet as if no one was watching (which no one was). Because no one was watching, I overshared. I overshare in life, so I overshared on the internet. I tweeted incessantly, and in 2017, I finally got an Instagram. I didn’t like how fake Instagram was, how everybody positioned themselves on it, and I was scared I would fall prey to becoming a Faker McCaker, so I avoided getting one. When I did get it, I learned that it was quite fun to post stupid shit impulsively. I enjoy trying to be funny. Slowly (and with very little expectations), I had somehow begun to build an “audience.” This “audience” appreciated how “honest” I was. The only reason why I felt any need to be honest, and why I still feel the need to be publicly honest, is because I’m terrified. I fuck up constantly. I’ve made a lot of mistakes over the years. I’m often ashamed of my behavior. I’m honest so that I can’t be yelled at for my fuck ups. I’m honest as protection, I’m honest with the goal of eventually being Free.

All of the tweeting and shit-posting winded up in a DM from the NYTimes in December 2021. A reporter told me that Stella Bugbee, editor of the NYTimes Style Section, had assigned him to write a profile on me. I couldn’t believe it. My friends couldn’t believe it. In fact, they didn’t. I lie a lot in real life.

When the article came out, my life changed instantly overnight. I got 42,000 new followers on Instagram in one day, which isn’t life-changing, but changed my view of myself. That Monday, my manager reported that I had meetings booked up for the next three months. These meetings were with producers, writers, directors, production companies, and (very few) casting directors.

In my first week of meetings, I pitched myself hard as an actress. I mean I really let myself cook there. I very quickly learned that the people meeting me were not interested in me as an actress. They were interested in me as an Interesting Person. I realized I should come up with something to pitch to these execs. I’d need a vehicle.

So, I wrote a short story about my haggard years in Los Angeles, and I separated the paragraphs into “episodes.” That’s how I got to writing a TV show.

When the NYTimes asked to profile me, I had told them that the Jane Hotel had booked me for a year-long residency. They hadn’t. I’d done one set for them in November at somebody else’s monthly sort of cabaret-residency, and I figured that if the Times fact-checked my “residency,” The Jane would want to say yes. They did.

I didn’t really want to do an hour-long one-woman show, but I had to. The tickets sold out in two hours - because of the Times piece - and I had no other choice. The first show was bad. I failed. I failed in front of 300 people. I lived in Chinatown; it sucked going to buy cigarettes.

My next show was my favorite show that I’ve ever done. Because that show went well, two producers reached out to bring my show to The Cherry Lane Theater that summer. I decided to write a new show, which was a mistake. I failed at the Cherry Lane, too. But I had written four hour-long shows in one year, and I needed to learn. Writing four shows prepared me to write a screenplay.

I hope all of this isn’t too braggy, too uppity, I don’t know. The honest part of me is pretty uppity. I must stress: I tried, and I tried, and I pushed, and I prodded, and, I cried, and I was broke, and I got no callbacks, and I auditioned tirelessly, and I “networked” for a decade in Los Angeles to no avail. I needed to do that. I needed it as it led me to learn what I’m actually good at. My writing needed those years; those years gave me something to write about.

I still haven’t figured out the money thing - I’m absolutely terrible at spending money (AKA keeping it) - and my first movie could be a massive failure. I’m good at being knocked down and getting back up, though. If there’s anything I’m sure of, it’s that I’ll keep putting myself out there. I’ll keep producing bad and good work, throwing it against the wall, and shamelessly self-promoting myself. I will continue to fail. I will continue to fail with the hope that the faster I do it, the faster I’ll learn.