We recently connected with Regina Sayles and have shared our conversation below.

Regina, appreciate you joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

I went to theatre school. When I finished college, I thought I was headed to NYC for a life of auditions and acting. WRONG! I had started singing acoustic solo gigs when I was in college to pay the bills. When auditioning in NYC was not helping me make very much progress after a year, I started booking more gigs in addition to being a substitute teacher by day. Over the course of 7 years, I detailed cars in an auto body shop, worked in a deli, worked as a real estate assistant, and was a substitute teacher during the day and played gigs at night and on the weekends. In 2012, I finally made the choice to go full-time and haven’t looked back. I currently play gigs, produce music, do session vocal work, am a remote adjunct professor teaching songwriting, and have a handful of private students. My goal over the next few years is to do more production and content creation so I can gig less on the weekends, but it’s going to take some time to build that side of my business.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am a vocalist who plays the guitar. I have primarily made a living playing cover songs, writing and recording original songs and teaching. My goal is to always help my students get to where they want to be faster than I did. There are no smoke and mirrors with me, what you see is what you get. The thing that makes people gravitate to me is I genuinely care about helping people. I am unapologetically myself and encourage everyone I come in contact with to find their truth because it’s very freeing. My brand is openly queer, down to earth and approachable. If you want to know how I did something, just ask, I’ll make you a YouTube video. If you want to talk about music, that’s great – but if you want to nerd out about video games, cooking, and traveling, let’s go!

I think people are afraid to ask questions sometimes. I solve my clients problems by being patient and helping them get the best musician/teacher for the job. I’ll explain the details so they know what they are getting. And if I don’t think I”m the right person for the job, I’m not afraid to refer them to someone I know will do it better than I could or is a better fit for what they are looking for.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

One of my biggest frustrations as a full-time gigging musician is getting paid for the time I put in. When people hire me for a 2-3 hour gig, that what they think they are paying me for. They aren’t thinking about my travel to and from the establishment, the set up and tear down time, the rehearsal time I may have put in, and the taxes I have to take out of the amount I am paid. I tell people when they book my full band, before we even get to the gig, I’m -$150 for the rehearsal space I had to rent in NYC. Non-musical people don’t think about things that like that. When I encounter people who do understand, they are often musicians themselves or are related to one.

Non-creative people think because creative people generally “love” what they do that that should be their payment. It’s so frustrating! I make it my business to kindly educate the non-creative folks as often as possible and if they still don’t understand, and we can’t reach a compromise, I will walk away knowing I did my best and didn’t lose any self-respect in the process.

Any resources you can share with us that might be helpful to other creatives?

As a singer/songwriter, I wish I would have learned to record myself so much sooner. I got really into audio production in my mid-30s. I tell all of my younger students to learn, it will make you a better singer/player and you don’t have to rely on other people to get your music going. I was so afraid to be the person pushing the buttons. DON’T BE AFRAID! Just do it!

Contact Info:

• Website: https://www.reginasayles.com
• Instagram: https://www.instagram.com/reginasayles/
• Facebook: https://www.facebook.com/reginasaylesmusic
• Linkedin: https://www.linkedin.com/in/regina-sayles-287a6a6/
• Youtube: https://www.youtube.com/@reginasayles
• Other: TikTok: https://www.tiktok.com/@reginasayles0
  Email: [email protected]

Image Credits

Image Credit: Kade Joy Photography (all photos except one)
Image Credit: Tyce Hoskins (photo in the theatre seats)