Today on I Wish I Knew, we have a double interview! One of the biggest decisions that artists have to make in their lifetime is: “Where should I move?” This question usually happens right after high school, or undergrad, or graduate school, but sometimes it pops up randomly in the middle of the year and you have to decide what makes the most sense for your career and your happiness. I’ve had to deal with this question many times in my life, and it has so far lead me to New York from California.

As this blog is designed to help aspiring artists get some insight before they make life altering decisions, I figured it was time to dig into the question “New York, Los Angeles or Chicago?” There are, of course, many other cities where you can have a thriving career, but these are the ones I’m usually asked about. I reached out to two of my grad school buddies, York Walker and Caitlan Taylor, who have had lots of experience in these cities, and asked them to break down the pros and cons.

York Walker and Caitlan Taylor

York Walker (he/him/his) was my classmate in grad school. He is a brilliant actor who has worked at American Conservatory Theater, Cal Shakes, Actors Theatre of Louisville, Two River Theater, and more. He is also a writer and his plays have been read at TACT (The Actors Company Theatre), and the Fire This Time Festival in NYC. He has lived in both New York and Los Angeles and has many feelings about both! Since he is an actor and writer, I wanted to ask him his opinion on what the best city for each of these artistic paths is.

Caitlan Taylor (she/her/hers) was also at American Conservatory Theatre for grad school when I was there but was a couple years below me. She has performed at American Conservatory Theater, SF Playhouse, Cardinal Stage Company, Chicago Shakespeare Theatre, and more. She moved to Chicago after school, and this is a city I know little about. I was so excited to hear what Chicago has to offer, and hopefully her awesome insight will help you get a clearer view on the Windy City!

Here we go!

Get to know York and Caitlan:

Q: York, when did you first know you wanted to become an actor? Did you study it in school?

I first knew I wanted to become an actor in high school. Prior to high school, I was obsessed with theatre and so I started doing plays in my basement with the neighborhood kids. Once I got to high school, I realized that acting was an actual career that I could pursue. In my last semester of my senior year, I decided to just go for it and see what happened.

Q: Caitlan, when did you first know you wanted to become an actor? Did you study it in school?

I can’t remember not wanting to be a performer… my mother and grandmother sang constantly and that’s how I got started – with a love for music. For as long as I can remember, I did choir, dance, theater…anything to be on the stage and performing. Eventually I went to a public performing arts high school (High School for the Performing and Visual Arts in Houston, TX) and this, in my opinion is what distilled everything.

I could talk a lot about Carnegie Mellon and A.C.T. and how much those programs shaped me (which certainly, they did) but my high school is absolutely to credit for everything. It was the sister school to the school “FAME “was based on and I love that I still run into alumni all over this country, in all areas of the arts. We were so lucky – we had an abundance of teachers and mentors that believed in us, believed in the value of the arts, and had the resources to give us a well-rounded education. It’s why I vehemently believe in the importance of having arts programs in our public schools; I’ve experienced and witnessed its powerful societal and psychological impact time and time again.

Q: York, when did you first realize that you are also a writer? How is writing a part of your life?

I didn’t start writing until my first year of grad school for acting. I remember there was a night when my class and I were talking about all of our past relationships and the drama that they caused. Something about the conversation sparked my imagination and the next day I woke up and wrote a one act play. I got my classmates together to read through it and some of it was terrible, but some of it wasn’t so bad.

My next play took a few months to write, but once I finished the first draft, I got my classmates together to read it. This time less of it was terrible. I kept working on it and eventually it became my first full length play.

Writing is a big part of my life now. I try to carve out as much time as possible in the week to work on whatever script needs the most attention. For me writing is an opportunity to tell stories without having to wait for permission to tell them. My mission is to explore the African American and/or LGBTQ experience in its fullness in my work. I try to make sure that I’m putting in the time to develop those stories, so that I can work on projects I’m passionate about, while also giving other talented actors an opportunity to share their gifts as well.

Q: Caitlan, what do you love most about acting? What’s the hardest part about it?

Telling stories is so important… it fascinates me that humans are the only creatures on earth that can imagine something that they have personally never seen or experienced. It is this unique ability to understand abstract thoughts, myths, and stories that allows us to cooperate in mass numbers around the globe! Telling stories, therefore, is not simply a sweet thing to do for a 5-year-old at bedtime, it is a critical part of our evolution and growth.

For me, the hardest part of acting is not getting to do it; it triggers a real grief and sadness that nothing else seems to be able to fill to the same degree. I suspect it affects many of us that way because that experience of being in a space with people, connecting and being present, the electricity and energy that moves through us in those moments is nourishing – there’s no greater high on earth. For me, this culminates best in live performance… the communion between performers and audience feels sacred; we’ve all come together in a shared moment in time – it can’t be recreated, it can’t be repeated. And when that balance is struck just right… when everyone in the space is present and embodied in that moment… we all feel seen and we all experience belonging.

York on New York:

New York City

Q: York, why did you first decide to move to New York and why?

I have always wanted to live in New York City. It seemed like the center of the theatre world and I always wanted to be a part of the theatre community in New York.

Q: What do you love about New York? What do you hate?

I love the sense of community you feel in the city. With the city being so compact, you are constantly surrounded by an incredible energy that carries with it a sense of urgency and purpose. There are also so many different kinds of people, food, and artists that live in this city. It’s hard to be bored here, because there is so much to be inspired by and do.

I hate that the train system is not reliable and that it takes so much effort to do basic things. Just going to the grocery store is an event. The constant walking can be hard on your body and sometimes being surrounded by so many people can be draining.

Q: In your opinion, is New York or Los Angeles better for aspiring actors?

I would say that New York is the best place for aspiring actors with a theatre background. You can get into an audition for a play in New York much easier than you can get into a TV audition in Los Angeles. With a background in theatre, you could possibly book a play that could lead to Film/TV work because casting directors go see theatre. In Los Angeles that is not always the case.

Q: What are some things you wish you knew before coming to NY?

1.Wear shoes with good support.

2.Monthly metro cards save you money and stress.

3.Finding and getting approved for an apartment will be awful but worth it in the end.

4.People are rooting for you to win.

5.Rats are more afraid of you than you are of them.

Caitlan on Chicago:


Q: Caitlan, when did you first decide to move to Chicago and why?

When I was a grad student at A.C.T., I happened to meet my now-husband, who was a Chicago actor and in production on the mainstage. It so happened that a lot of the actors that were in that show were from Chicago. When we started dating and I visited the Windy City, I fell in love. I had never been to the Midwest before (I have to confess, I always thought of it as flyover country) and no one in any of my programs talked about it as an actor market – it was always only LA and NYC. So, when Showcase came around in my final year, I decided to create my own little Showcase in Chicago – I met with agents and auditioned for several Casting Directors…from the start, we all just clicked and I appreciated the abundance of work here was well as the style of the work being created.

It’s a giant city with lots of different food scenes, neighborhoods, and people. The improv and comedy scene are huge and overall, people who are from here lovebeing from here. The pride and sense of community is infectious… plus, it’s all relatively affordable. Most free-lance artists can breathe a bit better here, have bigger apartments and overall have a nice quality of life. It’s a bustling concrete city and the hustle can be intense, but there are quiet spaces too with trees and backyards to grill in. To me, it felt like the best of both worlds.

Q: What do you love about Chicago? What do you hate?

The amount of work done in this city is astonishing – there are over 250 theaters, both Equity and non-Equity… everything from the big houses like The Goodman, Chicago Shakespeare Theater, and Steppenwolf, to gritty, intimate storefront theaters, to collaborative, mission-driven ensemble theaters. Everything gets reviewed, everything is respected – you’ve got directors directing the new Ike Holter play at the Goodman one month, then directing a new work at a non-equity space that seats 50 people the next. The film & television scene is growing every year, with shows such as Empire, Shameless, The Red Line, Chicago Med/PD/Fire (thanks Dick Wolf) and the commercial scene is also pretty big, thanks to the comedy world here. But the main thing I would want people considering Chicago to know about, is the giant network available here to support workshops, new playwrights, new plays, and experimental theater. Overall, everyone is game to dive in and there are so many avenues available to try something new and create from scratch.

I hate the winter -it can be brutal (strangely, most Midwesterners tend to take a perverse pride in it) but as a Texan, I find myself just counting the days until summer returns. Chicago overall is a giant Midwestern love story… spending most of my time in the Northeast and California, I thought I would hate it. But I’ve come to appreciate the hard-working and loyal attitudes that run strong here. People aren’t too stuffy – they’re open, authentic, and mostly interested in their families and communities, both chosen and/or born into.

Q: Can you tell us a little bit about the industry in Chicago? What makes it unique?

I guess I talked a lot about that in my previous answer… the only things I would add would be to first acknowledge the giant non-Equity scene here. It’s an important backbone of Chicago theater and I think it provides a good arena for younger artists to cut their teeth and for writers to find ready playmates.

I think another thing that makes it unique is the amount of theaters that have resident Ensembles. Some are filled with “stars”, but most are filled with local actors… and in any case, most of the more-recognized actors work in absolute parity with everyone and seem to be mainly interested in maintaining their theatrical roots. I think that’s why there’s such a strong undercurrent of “ensemble” here. Most Chicago artists value collaboration and teamwork above all else. A few examples are theaters like Lookingglass, with ensemble members David Schwimmer and Mary Zimmerman; Red Orchid Theatre with ensemble member Michael Shannon; Teatro Vista, a theater dedicated to featuring Latinx culture, playwrights and actors of color; Rivendell Theater Ensemble, a 24 yr. old theater dedicated to improving the lives of women through theater. There are so opportunities for someone to find an artistic home.

Q: What are some things you wish you knew before moving to Chicago?

  1. It’s difficult to move here as a 20s Equity actor. It’s takes longer to break in, thanks to the abundance of non-union talent.
  2. In winter, it’s not the cold that’s hard, it’s the constant grey.
  3. Buy a winter coat with a hood.
  4. Brush up on your history of the Mob.
  5. The city of Chicago is NOT like the rest of Illinois.
  6. Don’t ever go near the Addison redline stop during a Cubs game.

York on Los Angeles:

Los Angeles

Q: York, when did you first decide to move to Los Angeles and why?

I decided to make the move to Los Angeles in the summer of 2016. I wanted to start building the foundation for doing more Film/TV work instead of stage.

Q: What do you love about Los Angeles? What do you hate

I love the close proximity to nature that LA offers. It is so nice to be able to go on a nice hike or lay out on the beach when you need to clear your head. The weather is also unbeatable. It is especially nice if you do not like winter. I love having a car and being able to easily run errands without having to use much public transportation.

I hate the lack of community in LA. Everything is so spread out that it is hard to connect with people. There also can be a “Hollywood” aspect to conversations when you meet people. It feels as if everyone is trying to figure out if you are important enough to continue the conversation, which can be disheartening at times.

Q: What city do you think is best for aspiring writers?

If you want to write for Film/TV, I would say LA is the best place to start. There are lots of classes and networking events that can help you get your foot in the door. For playwrights I would say New York is the place to be. There are so many theatre festivals and competitions that are looking for new work from up and coming playwrights.

Q: What are 5 things you wish you knew before moving to LA?

  1. Lyft should only be a side hustle, not full-time.
  2. Check ALL the signs before parking.
  3. Pay your parking tickets on time.
  4. People are not as successful as they create themselves to be on social media.
  5. There is a tribe of people who will root for you to win.

Advice from both:

Q: York, what is a one of the best pieces of advice you’ve received?

I just heard this in André De Shield’s Tony Speech:

  1. Surround yourself with people whose eyes light up when they see you coming.
  2. Slowly is the fastest way to get where you want to be.
  3. The top of the mountain is the bottom of the next, so keep climbing.

Q: York, where can people find out more about you?

You can find me on Instagram/Twitter @issayorkchop

Q: Caitlan, what is a one of the best pieces of advice you’ve received?

The best advice I think I ever heard was from Ruby Sales (civil rights activist and theologian) – she said that an important thing for her to do when meeting new people is to ask herself, “Where does it hurt?”

She felt that seeking to understand and offering an interested presence in people’s pain, helped open doors for understanding and compassion and healing. She always tries to really look at people’s eyes…their color and shape. I think it’s harder for us to hate up close.

Q: Caitlan, where can people find out more about you?

People can feel free to check out my Insta: @caitlantaylor523

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