Shelby Kittleson

Living & Working in Chicago | Shelby Kittleson ’13

2013 graduate Shelby Kittleson moved to Chicago shortly after her graduation in May. Since then, she’s been thriving in her new environment and wanted to share her great story. We decided to ask her a few questions that might help you, our soon-to-be graduates, figure out what you want to do and maybe quell some of your fears about moving to a big city. Here are Shelby’s answers!

Tell us a little about yourself! What are your passions, goals, and what you do you love about living in Chicago?

I was an English and sociology major at Hillsdale, and every summer I worked at an arts camp near Traverse City called Interlochen. The camp is internationally renowned for honing the artistic skills in dance, visual art, film, theatre, music, and writing for kids ages 8-18. I loved the camp and I loved my studies, and always thought that I would be a teacher. One day while I was wandering I ended up in a book store and read Tina Fey’s Bossypants in one sitting and it just, clicked, so to speak. I realized that what I loved about that camp was not the youth development in general, but the idea of watching kids pursue the arts; seeing these tiny prodigies dedicate their summers to a craft was inspiring and exciting to me, and I decided to pursue the arts more wholly than I had at Hillsdale.

MPSK8My parents raised me on The Second City. My dad loved the alumni, like Bill Murray; I loved the newer names that I think our generation is more familiar with, like Tina Fey and Steve Carrell, and more recently people like Jack McBrayer. My mom took me to see a touring performance of The Second City at the Ark in Ann Arbor, and I knew I wanted to move to Chicago to be a part of whatever this weird art was.

I love living in Chicago because it’s the birthplace of improv comedy, in my opinion. Almost every comedian I love has his or her roots in improvisation, and improv will always thrive in Chicago with The Second City. I also obviously love having my best friend in the city here with me. Marissa and I actually had no intention of moving to Chicago together, but she happened to get an internship here the summer after graduation and we moved in together in the fall. Growing and exploring and learning the city together was delightful and exciting.

What position do you hold? Tell us about it!

While at Hillsdale, I worked with the Alumni Department under Joyce Curby, and she brought me to assist with an Alumni Banquet we held in March at the Union League Club of Chicago. One of the days we were working, Joyce put me in touch with Betsy Stone, also an alumna of Hillsdale who at the time was working in Group Sales for The Second City.  I moved to Chicago the 4th of July and started my job at Second City four days later. I started out as a hostess, seating people in the theatre and basically acting like a bouncer during the live show, but also sometimes doing dishes or running food from the kitchen. After about 6 months I was promoted to merchandising staff, and after a year of working for the theatre I moved to the box office and was relatively quickly promoted to box office manager. My current job as box office manager consists of selling tickets, creating shows on the back end in our ticketing software and managing aspects of our website, handling customer service issues, and making sure as many people can get in to our theatres to see great live comedy as possible. I held an Administrative Internship with the Production Team of UP Comedy Club, an affiliate of The Second City that mostly runs archival sketch material (stuff my dad’s favorite actors wrote while they were here), fully improvised shows, and stand-up. I’ve met some of my heroes through my job, like B.J. Novak, John Mulaney, Fred Armisen, and I’ve seen Phish and Paul Simon and Jeff Tweedy perform live on Second City stages. I’d like to one day produce these shows, which takes a lot of effort, and patience, and dues paid. Ultimately, I’d love to work in television, and move out to Los Angeles taking with me what I’ve learned here in Chicago about comedy and theatre and writing and producing and all things funny.

IMG_0001How did your liberal arts education at Hillsdale College help you score this awesome job?

There isn’t much live comedy at Hillsdale (though I see now that there are some improv competitions, which simultaneously inspire in me a lot of envy and excitement), but there is certainly a lot of humor. I feel I was academically groomed to understand a lot of lofty, intellectual, referential comedy through my English degree. I think Jonathan Swift, Mark Twain, and Jane Austen are hilarious. Human nature has and is and will always be quite comical, and the arts have done their part to capture that. I like to think that studying English and Sociology meant that I spent the better part of four years studying human character, and grappling with the great metaphysical argument (‘What is man? What is God? What is man’s relationship to God?’), prepared me to thoroughly appreciate the satirizing of the struggle to understand and to communicate and be human.

Do you have any advice for our graduating seniors?

Utilize the alumni network – Hillsdale graduates are doing amazing things in diverse fields all over the world. I’m so grateful to have gone to a small school, and especially such a unique liberal arts college, where just having signed the same honor code as my predecessors means we have something – the desire to uphold that code and to pursue a great education – in common. Being dedicated to Hillsdale College means forming a community of people dedicated to your growth and development, who are willing to help you however they can. Be willing to defend yourself in the workplace as a valuable commodity. Don’t feel boxed in to your major, and pursuing a career in that major. Invest in a nice coat. Save money to travel. Just because you have a degree from a small school doesn’t mean you can’t think big. Don’t let failure or fear of failure dictate your career. It’s sometimes valuable to start at the bottom and work your way through a company that inspires you, it can be a really humbling and exciting process.


Photos courtesy of Jill Frasier Photography and Shelby Kittleson.