How To Make It As A Traveling Indie Singer-Songwriter Or Band

by Kristen Gilles

in Exhortations And Musings,Music Business,Songwriting/Hymn Workshop

Closeup of Kristen Gilles playing guitar, photo by Kaiti Bierdeman

Me & my guitar, from Brooklyn to Texas and everywhere in between

For any of you who may be considering taking your independent music artistry to the streets or going on the road cross-country to share your story, I wanted to offer a little insight from my own journey and life on the road.

Listen to and Trust the Lord.

My journey began in my Brooklyn, NY apartment where I’d composed most of my songs and also made the determination to leave my full-time, well-paying and benefit-loaded legal secretary job to live out of my car and travel to unknown destinations to share my unknown songs. This was a HUGE step of faith for me, especially because I tend to meticulously organize every detail of my life that I (think I) can manage.

My life at that time, however, begged for this tremendous change of pace and routine and scenery, and God faithfully answered my continued prayers for wisdom and direction. He led me out with the greatest attention to every detail, and provided for every anticipated and unanticipated need. So, my first lesson learned was to surrender to God’s plan and fully trust Him. He’s carried me from before my birth and He will carry me home to live forever with Him.

Count the Cost.

Indie singer-songwriter Kristen Gilles playing guitar outdoors on street

I played everywhere. No, really ...

In the months before I hit the road as an independent singer-songwriter, I also spent a lot of time counting the cost and getting all of my financial ducks in a row:

  • I paid off ALL outstanding dept so I’d have no obligations looming over my head on the road.
  • I worked and saved as much as I possibly could.
  • I trimmed my monthly expenses down to bare minimum. My only monthly expenses at the time I hit the road were my cell phone bill and my car insurance (and gas and food, of course).

In the process of packing and preparing to leave, I invited friends and neighbors to my apartment where I sold or gave away everything I owned except for what I needed to live on the road (which, including my guitar and keyboard, some other essentials and a few mementos, all fit very snuggly in my 4-door Kia sedan).

Get Wisdom and Understanding.

Another part of counting the cost involved my seeking out wisdom from experienced indie musicians/songwriters that had already lived some of their lives on the road. God provided much wisdom and experience from Tara-Leigh Cobble, a close friend who has been living on the road for several years now as a singer-songwriter and speaker. She freely shared many lessons that she’d learned—and she helped me make some profitable connections with others who could support me.

Communicate and Contact.

Singer-songwriter Kristen Gilles having fun during the Embrace The Bigger Picture photo shoot

Having fun during the Embrace The Bigger Picture photo shoot

Once I knew I was going on the road, I gave plenty of notice to my current employer that I’d be leaving at the end of the year. I was so blessed by God’s grace to me in having my work family give me a hearty send-off.

In the meantime, I also attempted to contact every person I’d ever met across the U.S. and Canada to let them know of my plan to live as a traveling singer-songwriter, and my need for a place to lay my head along the way. Many of them had already extended invitations for me to stay with them whenever I was in the area, and now was the time to take up those offers.

I also asked them to forward my contact information to anyone they knew who’d be interested in having me sing at their venue. I heard back from enough people and confirmed enough “anchor” events/dates in select cities that I was able to chart a small tour to get me started.

Hit the Road!

So, on January 1, 2009, I hit the road. I went first to Michigan where I stayed with my music producer friend Brad Kelly and his family for two weeks while he and I worked on recording my 4-song EP Embrace The Bigger Picture. This was a project we’d been planning by phone and email for several months, and I’d been saving for it too so that the project was entirely funded before it was finished. I didn’t want to incur any debt since I didn’t have a steady source of income on the road.

Cover art for Kristen Gilles's Embrace The Bigger Picture (she went by "Kristen Gabrielle," using my middle name

Cover art for Embrace The Bigger Picture (I went by "Kristen Gabrielle," using my middle name)

The EP was an important tool in sharing my music and opening doors at venues where I could play live. And the fact that the EP was paid for allowed me to give it away whenever appropriate.

Be A Good Guest!

I was blessed to stay with several families throughout my tour; they were all incredibly hospitable and gracious to me. Before I hit the road, I determined to be the most low-maintenance, easy-going, thankful and helpful houseguest I could possibly be wherever I was staying. I offered to do any and every chore that needed to be done, and to pitch in for food costs, etc.—whatever I could do to be a blessing to my hosts.

I also made sure I took short showers and didn’t use too much electricity so as to keep utility costs as low as possible. I communicated appreciation to my hosts every chance I could, and I left thank you notes for the family members when I departed.

Ongoing Event-Booking

Throughout my time on the road I worked hard to book shows at whatever destination God led me to by contacting every coffee house and open mic venue in that city in advance of or upon my arrival.

Almost every coffee house welcomed me. Of course, it was on the condition that my only pay would be a complimentary beverage and whatever was put into my tip jar. There were nights I’d play at a packed-out suburban Texas Starbucks and walk away with only a buck in the jar. Other nights, I’d leave with $150. It was very unpredictable, which encouraged me all the more to live very frugally and thankfully.

My experience on the road was unique to me, but some of the things I learned are applicable to any singer-songwriter or indie band that chooses the adventure of life on the road. I hope this is in some way helpful to you if you’re considering the journey. It’s going to be an adventure, even if it’s not always easy or comfortable, and it will definitely bring you to the end of yourself which will leave you so much closer to God, your Maker and Guide.

All photos courtesy Kaiti Bierdeman except Photo 3, by Sarah Sutherland.

Embrace The Bigger Picture cover art by Pamela Kay Miller.

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