Milwaukee Artist You Should Know: Caley Conway

An interview with Caley Conway

Caley Conway thought she had everything she ever wanted in music. People asked her to share the stage, audiences came to listen to her perform and clapped at the end.

Last year took the Milwaukee artist on a journey that included performing in a choir with Phoebe Bridgers and Julian Baker as well as joining Field Report as a guitarist and vocalist. Now with a new EP and a bank of demos for what’s next, Conway continues to expand into the unknown future.

Read below for an interview with Caley Conway, who is releasing her EP “Surrounded Middle” on April 18. See her live at Anodyne Coffee Roasting Co. at 7 p.m.

How did you get started playing music, and when did you start writing your own original music?

I was always singing and dancing as a kid. It wasn’t a conscious decision to run off and start singing. I watched a lot of musicals with my sisters and sang along to Grease tapes and made up choreographed dances, and my sisters and I were also Irish dancers. My mom got us into piano lessons at a really young age. I was reading piano music for as long as I was reading regular words. Not that my piano/sight-reading skills speak to that today. I try not to dwell on it because there are other ways to express your skill musically than reading notes.

I started playing guitar when I was 12 or 13 because my dad and mom both play. My dad is left-handed so he taught me on my mom’s old nylon-stringed guitar from when she was 12. He taught me basic chords and riffs and that’s what I stuck with. It never occurred to me that I would be writing my own songs until college.

I feel like college is when a lot of musicians start writing original music. I wonder why that is…

It could be hormonal because of the certain age that you are. It could be a phase of experimentation…

When I started, writing was in correlation with my drug experimentation. I think you’re more willing to explore corners of your consciousness that maybe you didn’t even realize were inside you. You’re exposed to new people and you’re freaking out in a lot of ways.

When I was in college, I was really lonely and using my guitar as my buddy, for comfort. I would do covers to keep myself entertained, and it gradually morphed. Once I started doing it, it became something instantly gratifying, maybe therapeutic.

I was thinking about how I never saw a female musician perform shows when I was younger. I wonder if that affected me. If I saw women play and no men, would I have started playing in bands earlier?

I lose sleep over that. Thinking about those real youthful, formative years. Friends getting together and being terrible, but so excited about what they were doing. Playing with each other. If you do a consensus, a high majority of people encouraged to have that experience or who fell into it are definitely men. Meeting up in their parents’ basements or garages, playing really derivative and awful punk and metal, but whatever it was…

…it was an option. A lot of men I interview say they were encouraged by their parents at a young age.

That’s really interesting. When we’re that young, in middle school and stuff, you’re cool and you’re not a kid, but you are a kid in terms of instinct to play in your free time and play with one another. I really do feel like I missed out. Now, it’s not so playful anymore. It’s not getting together to play an imaginative game, we’re getting together to get something done.

Even if you boil it down to how many times I’ve been able to play guitar with someone else playing live drums with me, it’s not that much at all. Now that it’s my music and I’m accountable for everyone’s time, I don’t have people playing with me just to play. Part of that is definitely a choice. Maybe as a result of that gendered upbringing, I might even be hesitant to throw myself into an improvisational or playful scenario. It’s probably me holding myself back.

This story is from our partner 88Nine Radio Milwaukee.

Find the full interview with Caley Conway on 88Nine’s website.