Meet Conner Cherland | Music Artist

We had the good fortune of connecting with Conner Cherland and we’ve shared our conversation below.

Hi Conner, what was your thought process behind starting your own business?
I started playing music gigs back in 2014 when I got out of college and was working a full time job. I would play one gig a month, and then two a month, and then one a week, and then three a week. Once I was playing three gigs a week I started to feel like I hit a ceiling – I could do more gigs if I didn’t have this day job, or I could get a promotion if I didn’t play so many gigs. I decided to spend my youth on the riskier option, leaving the safety of a matched 401k and provided healthcare.

Looking back, the decision was the perfect mix of idealism and practicality. I knew I needed to get more gigs and learn how to improve my skills and network, but I didn’t know how constant that exact problem would be. My thought process today is about the same: find more work to pay the bills and continue to make art that moves me.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
One of my defining traits is being willingly and consistently vulnerable. I’ll show you my best at every stage of my development. It might come across as shameless, or lacking self-awareness at my own inability…but it’s quite the opposite. I meticulously strive to live a life where I celebrate doing the best I can do, even if it’s not as good as the next person. In keeping this practice, I think I’ll be able to give myself the best odds at real lifelong progress.

What I’d like the world to know about my story is that anyone can live an artistic life full of vulnerability. I’d like to be a symbol for what quiet courage looks like in pursuing that.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I live in Highland Park so I’d recommend my neighborhood because I think it’s the best. I’m not sure if you’ve been to Kitchen Mouse…but it’s got the goods…flavor packed in there like you probably haven’t experienced. There’s also Gloria’s right down the street and I just had their plantain breakfast yesterday and it was righteous.

For lunch/video games I’d go to Barcade on York, and then I’d go back to my place for more video games, and then to the Highland Park Bowl to bowl a few games, and then (I’m assuming I have infinite money in this question…I don’t usually stack so many fun activities) I’d go to The Goldline, and then catch a show at the Lodgeroom. Oh what a day that would be.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
Absolutely. I’d dedicate this to my wife, Layne. There have been so many moments that I’ve wanted to quit this job, when really all I needed was someone to recognize my hard work and love me. I wouldn’t be doing this job six years later without her support, creativity, and encouragement.

Website: https://connercherland.com/gofundme

Instagram: https://www.instagram.com/connercherland/

Linkedin: https://www.linkedin.com/in/conner-cherland-391b3b36/

Facebook: https://www.facebook.com/connercherland

Youtube: https://www.youtube.com/@itsconnercherland

Image Credits
Josie Farrior Layne Deyling Cherland Robiee Z.