The Funny Part: My Time as a Wannabe Comedian and How It Almost Killed Me

By the Spring of 2015 I had successfully dropped out of my theater undergrad degree, built (and then quit) a career in sales, officially launched myself as a full time freelancer and moved back in with my mom because full time freelancers don’t make consistent enough money. I was 21 and felt like I had already experienced a lifetime of trial and error. But I had one more thing I hadn’t done: Move away. Like, away, away. 

I was listening to the audiobooks Bossypants, Yes Please!, and Girl Walks Into A Bar, by Tina Fey, Amy Poehler, and Rachel Dratch respectfully, on my way to and from my day job at a craft store when the idea came to me. Had I ever wanted to be a comedian before this? No, but I had always been told I was funny and charming so how hard could it be? In all of these books the comedic goddesses all mentioned the same place as being their foundational cornerstone: improvOlympic in Chicago. That's where they all got their start, even before they went to Second City. I just knew that's where I was going to get my start too.

I had a friend from my one semester in college that lived in Chicago and I talked to her briefly one weekend about moving and she said I’d be welcome any time. I took that perhaps a little too literally. We talked about me visiting on a Sunday and by that next Thursday I had a large duffle and a one way ticket and I was on my way to becoming Chicago’s next best comedian.

 I had my job transfer me to the nearest chain store in Chicago but since I left all my freelance clients back in North Carolina I wouldn’t have any money for rent. My college friend and her roommates set me up with a sweet deal though. They had a back porch with a loft storage area that had a mattress in it. I could stay there for as long as I needed to and I did… For three months. Thankfully, these kind strangers didn’t charge me a dime while I stayed there. I saved most of my money but one thing I splurged on: classes at the infamous improvOlympic.

I met a few friends at the comedy club. Some were in my same classes and some I would just so happen to be seated next to when I went to shows. Comedy, I’ve found, is the fastest way to make new friends. That and hating the same things. One of these friends told me that sometimes sketch groups will look for scripts that they can perform on stage. Ding, ding, ding! Opportunity! I wrote sketches that were so horrible I’m glad cloud storage wasn’t all the rage it is now because if any of it got out I would die of embarrassment. But you know who should be more embarrassed? The dumb asses who bought the scripts. Yes, I was quickly becoming a working writer in the Chicago comedy scene selling scripts for the hefty price of $15 a pop (sometimes I would accept a slice of pizza at Whole Foods across from the club if I was desperate enough). 

I was making somewhat of a routine for myself. I would work at the craft store during the day, the comedy club classes and some ushering for them in the evenings and night, and any of my freetime was spent writing. Anything I didn’t sell I produced myself for YouTube, thank God for the delete button. And even my freelancing was picking up with an odd thanks to Tinder and MTV. I matched with a guy who was in the running to become one of MTVs 2015 Summer Artists to Watch. He requested me specifically to do his shoot for him and… well… its a very funny and stupid story that I will tell at another time. Just know this: I was popping off! 

Then one of the roommates in the house was leaving. A real room was becoming available and I was one of the candidates. I was making enough money now to afford it and I was in good standing with everyone in the house so I thought it was all but certain. Turns out I had been so focused on what else I was doing I wasn’t focused on what was going on around me at all. The roommates were not thrilled with how I was pitching in with the house, how I was keeping odd hours, having visitors without permission, stuff I really should have kept an eye on. Instead of getting the room they politely asked me when I was moving out. 

It didn’t take me long to find my next place. I was browsing craigslist when a sweet woman’s face came up. A nurse living not very far from my back porch. I was able to move with the same duffle bag I came to Chicago with and bought a broken air mattress from goodwill so that I didn’t have to sleep directly on the floor. It was technically a one bedroom apartment but Craigslist Carrie took the alcove off the living room and I took the actual bedroom.  I was excited about the move. It was a direct shot to the comedy club, maybe a 20 minute walk, and it was across from a Dunkin. Win, win. One issue though: I would have to pay actual rent and besides what I had saved up, I wasn’t necessarily able to afford this place for long without changing something. This is when Tinder came in to help again!

Money was running thin when I matched with Roberto. He was a mid-40’s single guy working in tech and living off of Lakeshore Drive. He was very well-to-do. He never let me pay for a single meal, took me out almost daily and, the best part, he would take my laundry weekly and do them in his apartment so I wouldn’t have to go to the laundromat. I was getting spoiled. With Roberto covering almost everything else, I was able to cover rent. But something about Roberto and me… I wasn’t attracted to him at all. I had several other flings while in Chicago but Roberto was the one that I really was in the wrong for. I used him for his washing machine, used him for his 3-story walk up that had a jacuzzi tub, for the diner breakfasts he took me to almost every day. But I didn’t like him at all. I’ll save the details for my memoir someday but shortly: he found out I had no feelings for him and we split. Now I was in deep shit. 

My MTV and freelancing money was sporadic and unpredictable even with me getting more clients. My job at the craft store was a mind suck and arguably cost me more in fares to get there than it was worth. I was still paying for my improv classes but hadn’t sold a script in a while. For a month or two after Roberto I flushed through my savings and opened a credit card to live off of. When it became really tight the first thing I would give up was food. I started by excusing myself for breakfast here or there. But then it became the fact that I couldn’t afford groceries. I began to lose weight fairly quickly. It was a mixture of not eating and the fact that my transit card ran out and I couldn’t afford a refill so I had to walk everywhere. This dream was unraveling faster than I could pull the pieces back together.

I had been in the city for 9 months when on one rainy day in November I woke up feeling light headed. I knew something was wrong as I walked around the apartment getting ready and could hardly keep myself up. I needed to go to work but I knew I couldn’t make the walk today. I had enough on my card for the fare so I dragged myself down the stairs and to the bus stop where I waited patiently under the umbrella. That’s the last clear thing I remember. 

I flashes of what happened after. I’m on the ground looking up and people are all around me, the rain on my glasses making my vision splotchy. Then I’m being hoisted up by strangers and Craigslist Carrie is screaming behind me giving them directions. I vaguely remember being on the air mattress with Craigslist Carrie pacing around my room on the phone. My next full coherent thought is a few days later. I woke up in my teenage bedroom. I was back in North Carolina. 

I have ideas and some other memories of what happened. Without placing blame or saying much I’ll just say that with outside “help” my credit card was used to book me a flight back home. I had been so malnourished for so long that I was slipping in and out of consciousness. While now in hindsight I can recognize that I had put myself in a horrible position, all I could see once I was home was that I had just destroyed my dreams. I destroyed my chance of getting out of my small town and making something of my life. 

It took me six months or more to get over this feeling of defeat. Sometimes I still feel the shadows of those thoughts pass over my mind. I’ll never know if I would’ve actually become a comedian. I think we’re all for the better that I didn’t. But I do know that when I feel ambitious enough I can get shit done. I can move halfway around the country and start from scratch. Through all of that quagmire of shit I learned the lengths I would go to to make something happen for myself. While I wouldn’t want to do it the same way, and it caused way more far reaching ramifications for my mental and physical health, and may have left out some other details here and there, I still don’t regret it. 

So make sure if you laugh at anything I ever say you make sure its genuine. If it's not, I might take it seriously anyway and run away to join a circus.