
Today we’d like to introduce you to Conner Cherland.
Hi Conner, thanks for joining us today. We’d love for you to start by introducing yourself.
I started writing songs in 2014 as a journaling exercise. I’d ride my bike to work at 7AM, bike back at 4PM and lock myself in the bathroom and write songs. I challenged myself to write 40 songs in six months, understanding that if I couldn’t write six good ones out of 40, then the odds were against me and I should quit forever. Lo! To everyone’s surprise, I wrote more than just six good songs, put them on an EP, and continued the practice ever since. At this point, I’m over 200 and continue to hone those skills regularly. In 2016, I quit my tech job, got married, and became a full-time musician! The past four years have been a roller coaster, but I’ve made a living wage each year and continue to forge a career that itches my creative needs without leaving me financially lacking. I’m currently releasing my 5th collection of songs, “Love Songs by Conner Cherland”. The first single released 2/12 and I’ll be releasing three more singles prior to the album in June.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
I don’t think “professional musician” is a road that’s bound to be smooth for anyone. It’s an entirely made up career where you say to the world, “You will pay me to sing my original songs.” It’s a bold declaration. Because I look way younger than I am – I’m 29 but could pass for a freshmen in college – people think I’m a sap, give a lot of unsolicited advice, touch my knobs while I play, and overstep my boundaries. I called a guy once a week for six months to get him to pay me. I’ve stomached a call from a grumpy business owner telling me that I’m not worth my rate. Now I’m living through the papa of all millennial struggles, COVID-19. It’s a doozy. I’m pulling out all the stops to make ends meet: door to door sales to pitch outdoor concerts, online beer and music events, and spare time pickleball coaching.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’m a thoughtful man who writes a lot of songs. I’m known for witty stage banter, prolific songwriting, and a real can-do attitude. I’m not really “known” for anything on a large scale. In my hometown (Lancaster, CA) I was the volleyball guy. In Santa Barbara, I’m known as the music guy or that quick kid with the white hat on the pickleball court. I honestly don’t believe I’m more talented than most people, but I know that if I keep applying myself over time, I’ll improve and move ahead just like any other great talent. If anything, I think I’m much more intuitive than the average man. My gut leads me in beautiful and strange directions both in songwriting and in life. This leads me to make songs that resonate, and it leads me to meet people who I treasure.
Is there any advice you’d like to share with our readers who might just be starting out?
For those starting out, I’d say to be gentle with yourself. Most musicians don’t like writing songs because 4 out of 5 sucks. But, some of the best songwriters will tell you that their numbers look the same! So don’t quit just because 5 out of 7 sucks, rejoice that 2 out of 7 are pretty good. I wish I knew when someone was unintentionally lying to me about the upside of a gig. I’ve spent way too many hours gigging for a promise of a paycheck that never came. Prioritize gigging for people who pay, and let everyone else move around that schedule.
Pricing:
- Socially Distant Outdoor Concerts: Free-$300 Minimum depending on where you live
Contact Info:
- Email: [email protected]
- Website: ConnerCherland.com
- Instagram: @connercherland
- Facebook: @connercherland
- Youtube: https://www.youtube.com/user/itsconnercherland

Image Credits:
Josie Farrior
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Aleasha Bahr is a sales & marketing strategist known for showing introverts and ambiverts the Secret Art of Subtle Selling. She personally sold millions in revenue while discovering introverts are usually top sales people – as soon as they stop trying to act like extroverts. We’ve partnered with her to produce Introverted Entrepreneur Success Stories. Check out episode 1 below:
