How and Why I Moved To Chicago (Spoiler: This Blog is Too Long)


In 2006 I performed stand-up comedy for the first time in front of a couple hundred high school nerds at a speech and debate tournament in Joplin, Missouri. It was part of a competition. I won first place. I also won the following year.

In 2009 I auditioned to be on an improv team, not because I had any interest in improv (in fact, I did not have any interest in improv), but because I thought some skill in improvisation might improve my stand-up act and presence. Soon I was doing way more improv than stand-up. Then I was doing one stand-up show for every four or five improv shows I was doing.

In 2010 one of my best friends, and my first improv teacher, moved to Chicago, the improv comedy Mecca.

In 2011, while I was finishing up college by completing my student teaching in high school English, I dramatically and quietly played with the idea of moving to Chicago. But for this to happen, three other things had to happen first:

  1. I had to graduate college.
  2. I had to be heartbroken.
  3. I had to not have a teaching job lined up.

Before even graduating in the spring of 2011 I had a teaching job lined up for the fall of 2011. Two out of three wasn’t good enough to move.

In 2013 – on this last Wednesday, actually – I moved to Chicago, leaving my job, hometown, family, and longest friendships behind.


I’ve been crazy lucky the last two years. Teaching high school English was exactly what I was supposed to do between the fall of 2011 and spring of 2013. I taught sophomores and juniors – English 2 and English 3, respectively – and I thanked the sweet and merciful Lord every day that I didn’t actually teach freshmen (both years, however, I did have a “Learning Lab,” which is basically a study hall, which contained only freshmen, in which I got to know a few amazing students and practice my babysitting skills on others).

My hallpass. The Snodpass.

I never loved literature, analysis, symbolism, poetry, rap music, or spontaneous creativity more than when I was teaching English. Though I had brilliant and helpful professors in college, I learned more about literature in those four short semesters as a teacher than I did in those four short years as a college student. As a teacher I used rap to teach poetry, I used Pink Floyd to teach Animal Farm, I used Rush to teach The Crucible, and I read The Catcher in the Rye, The Old Man and the Sea, and Of Mice and Men for the first time.

Teaching is a steady job with a relatively piddly paycheck and a great retirement. And teachers get summers off! I got to be in charge of the grades of over 120 kids each year. I got to lovingly boss people around every single day. I got to be a mentor in the eyes of some, a charming nerd to some, and a ruthless b-hole to some. Each day I got to dress up nice and perform for a room of diverse people (certainly more diverse than an open mic – have you ever been to one of those? It’s 98% white dudes in their mid-late 20’s that also wear plaid and almost have a beard). My performance is just being a less-lazy version of my natural self, a mostly true character whose mind is laser-focused on HOW COOL BOOKS ARE! Once I got to spend an entire class discussing the badassery of Hemingway. And I got the job at the right school. In the middle of the mostly-white, conservative-church-going-marrying-at-age-18/liberal-college-attending-art-walking identity crisis that is Springfield, Missouri, my well-populated and middle-of-the-city high school was like a little Chicago, diverse and bustling, I was paid to visit five days a week. Teaching was fun, intellectually engaging, and rewarding.

Hemingway, people! He’s from right near Chicago!

Teaching was also at times frustrating. Each class has a different personality, and those personalities are just as unpredictable as the moods of the students that compose them. I only started drinking coffee because of the job. It was so early (also, I didn’t know what to do with my hands, so holding a mug was easy). Most of my friends were still living a collegiate lifestyle – staying up late, waking up later, drinking, going to concerts, saying whatever they wanted on Facebook and Twitter… While I did love my job, I’d be lying if I said I didn’t envy parts of that lifestyle as I went to bed while weeknights of fun continued without me. I was a grownup now. And it seemed like part of being a grownup meant being perpetually sleepy, spending free time creating or grading assignments, and going through phases of emotional and physical exhaustion. I stopped doing stand-up for months. I couldn’t stay up late enough to make the shows. But my improv shows [at the wonderful Skinny Improv] continued (those shows took place earlier and only on weekend nights). I even “sponsored” (“coached?” “taught?” “tried to grade during?”) my school’s improv club, which was full of shockingly, truly surprisingly funny 9th graders (9th graders are not usually funny on purpose). Oh, there were other grades that joined too. But it was mostly freshmen. Being a part of that was one of the best things I could have done with my time as a teacher.

In 2012 I was finishing my first year of teaching. I had planned a trip to Australia to travel with my friend Scott. I needed time outside of Springfield – outside of the country – to relax, explore, and distract myself. The nine months of routine had made me really happy, somewhat creatively unsatisfied, and left me with some mixed feelings about my future as a teacher.


I was really creative in Australia. Even when I didn’t have internet, or an electrical outlet for my computer, I was writing. Writing short stories, lists, lyrics, jokes, journals. Many of them terrible, and many of them wound up on this blog (and probably some of those are terrible, too). Scott and I lived in Sydney with his older brother, did improv when we could in Sydney, and then spent 14 days traveling around close to half the circumference of the country. Australia was not a vacation (nor was it supposed to be); it was an adventure. I needed an injection of new experiences, I needed a breath of fresh air (both literally and metaphorically, I suppose), I needed something to scare me.

It was in that rented camper van, on those flat, long desert roads of the Outback when Scott and I agreed that we should probably both pursue something in Chicago. Our jobs were jobs we could theoretically return to if we ever give up or go broke in the big city. There wasn’t a better time than now.

Except there was, and it was in 11 months.

Co-hosting a show in Springfield.

We agreed to give ourselves time to save money, do as much improv and writing as possible, and try to hit the ground running in Chicago in May of 2013. Australia was practice for a more permanent kind of adventure.

While I could take an “adventure” each summer as a teacher, I was scared of later being too scared to try this dumb comedy thing my brain had teased itself with since I graduated college…since I opened for Mike Birbiglia in college…since making awful sketch videos in high school…since quoting Mitch Hedberg jokes in 7th grade. The city of Springfield, Missouri makes falling in love, buying a house, having children, and never leaving your good job seem a little too easy. Frankly, that “get a family goin’ quick!” timeline always felt encouraged. For a long time I assumed that’s what I would do, that’s what we’d ALL DO! That it was Midwestern destiny.

(Almost everyone I told about my intention to move enthusiastically told me to go for it. Especially people older than me, and especially if they had families; my fellow teachers were especially supportive and encouraging. This variety of people I spoke with rarely seemed unhappy with their families, or something, they would just say “now’s the time to do it.” But, really, though: So many people said that exact phrase to me. “Now’s the time to do it.” There was too much consistency to refuse such wisdom.)

The end of my stand-up set on The Mystery Hour, a local television show hosted by my hilarious (and traveling/risk-taking) friend, Jeff Houghton.

But I don’t dislike Springfield. I love Springfield, actually. Kids always complained about our town in high school, and some did in college, too. They’d say things like “there’s nothing to do here,” or “Springfield is so lame” or whatever. Those people are idiots. They’re boring idiots. I can’t remember the last time I was actually bored. Springfield gave me a lot to do. It allowed me to make friends, play music, perform comedy, write for a TV show, write for a famous Russian comedian, and drive anywhere in the city within 20 minutes! Springfield is really great. I’d be happy living in Springfield. But I’ll be happier if I took a risk in Chicago. Maybe the risk is for a long time. Maybe for until I wind up somewhere else. Maybe only for a short while. Whatever happens, the experience will be worth it.


So here I am now in Chicago. Still new to everything. The romance I have for this glorious metropolis hasn’t worn off yet.

About to leave my parents’ house early in the morning. I’m a feeling a unique combination of excited, sad, and tired.

Similarly to my journeys through Australia, I’ll use this blog as a way to update anyone who cares about my comedic or life-related attempts, triumphs, screw-ups, and discoveries. And when I say “anyone who cares” I really mean my mom, my grandparents, and maybe a few other friends if they’re bored at work or something. I haven’t blogged much since I started teaching again in the fall. And I’m stoked to have some time to write again.

I doubt it’ll be all “updates.” But those will be here. And I have to clarify: I am not assuming that anything about me makes me more special than anyone else trying to do what I’m doing. Hopefully there is something, but I don’t know what that is yet. I just know I want to perform/write comedy consistently and not starve. I’m not in Chicago to be famous. I’m here because I love comedy, and Chicago is an excellent place to learn it, consume it, and be immersed in it. And “now’s the time to do it” after all. Simply by trying comedy here I get to follow in the footsteps of Tina Fey, Chris Farley, Adam McKay, Amy Poehler, Matt Besser, Pete Holmes, Hannibal Buress, the three newest SNL cast members, many more who have made it work out, and the thousands who never made it work out.

With this move, this new place, this new risk, I don’t know what’s going to happen, but I know I’ll grow and it’ll be fun. It’ll be worth it. And it has to be. I left a lot behind for this. I made students cry for this. I made my grandma cry for this. So this risk has to be worth it.


8 thoughts on “How and Why I Moved To Chicago (Spoiler: This Blog is Too Long)

  1. I could seriously cry. I am so incredibly proud to know you. I remember when you started teaching, I thought to myself…he will be a great teacher, but he would be an awesome comedian. I have no doubt you will succeed where others have failed. You are that talented. I have that much faith in you. There are no limits on what you can do. Metaphor, metaphor, accolades, some more accolades, gratuitous flattery and a great big ole “I love you man!” And good luck!

  2. Pingback: Facts About Italy | [The website and blog of] Tyler Snodgrass

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