Meet Bailey Lehfeldt | Singer Songwriter

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

Hi Bailey, what role has risk played in your life or career?
Ever since I was in my teens, I’ve always been one to take risks. The first risk I ever took was at 15 years old when I dropped out of high school. It was partially because I wanted to try and pursue theater professionally, but also due to the fact that I had severe social anxiety. I knew from a young age that traditional education was not for me, and with the support of my parents, I decided to take that jump. In my new found free time I became an obsessive writer and avid reader. I ended up building my own curriculum at home for myself and taught myself everything up to a college level (aside from math, I suck at math. Shout out to my old tutor Grace).

While I don’t regret the risk I took dropping out of high school, I can’t deny that the ridicule one may receive after dropping out of high school is not easy to deal with. After a while of being labeled “lazy” or “stupid” I decided to return to school to prove a point. I got my GED at 19 and returned to community college. I set my sights high, with my top three transfer college choices being Columbia University’s School of General Studies, Boston College, and University of Virginia. I was accepted into all three. However, I always knew I wanted to be a songwriter, and so while I initially committed to Columbia, I ended up deferring and applying to Shenandoah University’s Conservatory. I realized that following my heart was more important than proving a point.

However, I also realized that taking great risks leads to great stories. Not only has this philosophy shaped my life, but it’s shaped my writing and career as well.

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.
I’ve been passionate about telling stories my whole life. I wrote my first story when I was in 3rd grade. It was 80 pages in a composition book, and I even illustrated it. When I was 2 years old, my grandpa noticed I could sing, and so my grandparents began to encourage music. By the time I was 7 years old, I was in vocal lessons, and by the age of 10, I was performing in my first professional show at Toby’s Dinner Theater back in Maryland, which is where I’m from. I continued to pursue theater professionally as a kid, but as I grew up, I began to fall out of love with it. I shifted my focus towards contemporary music and songwriting.

When I was 14, I began attending the local open mic at a restaurant called Agrodolce in Germantown, Maryland. This is where I met Pete Looney, who changed my life. Pete was a great singer songwriter who ran the open mic, and always encouraged a fun, welcoming, safe environment for musicians to play in. I used to be so scared to play my originals that I wouldn’t even say I wrote them, but Pete caught it, and told me that I should be proud of them. He encouraged me to continue to write more. He is the reason I am a songwriter today. He sadly passed away a few years ago, but I know he will always be remembered as a legend in my Maryland community, as he should be.

I’ve always been a very adventurous person, because I like to believe that in order to write a good story, you have to live a good story first. So, as I’ve grown as a person, and a songwriter, I’ve worked hard to challenge myself, and to take big risks with my art. I’ve also made it a point to document as much of it as I can, so while I write songs, I also journal every day of my life. I am now on journal number 13, and over the last 6 years, have written over 3,000 pages, detailing my experiences and journey, so that when I’m writing music, I can go back to the day that inspired it, and relive every detail. I interned at the Library of Congress for a year, and my time there made me recognize the importance of historical documentation within art and storytelling, so I try to take that research experience with me as a musician everywhere I go.

That being said, some of my favorite stories and songs that I’ve written about so far, have been about my time spent on The Lost Coast of California. If you’ve never heard of it, it’s an area in California that’s about 4-6 hours North of San Francisco. It’s pretty isolated, and a little off the beaten path, but the stories that live there are worth the adventure, so every few months I throw my tip jar, guitar, and sound system in my car, along with a memory foam mattress pad- and I go get lost. I play at small intimate venues along the coast, car camp, and write. My goal with my art is to find the stories tucked away in hidden communities and to highlight the beauty of them and their philosophies, eventually playing those stories in new towns, so that I can connect communities throughout the U.S.A., and bring people together through music. I want to encourage old school community and connection again, with a sense of humor, of course- by not only writing about aspects of the human condition, but by also documenting unique places in song.

My upcoming release of my song Cherry was kind of the song that started it all. It’s a song about finding your individuality before committing to someone else (and about not wanting to get stuck in the suburbs). I wrote this song to challenge my fear of getting stuck, and the philosophy of this song is the reason I car camp and play shows on The Lost Coast, because that is the absolute LAST thing that the character I wrote about would be doing. I love using my music to challenge my own growth, and I can only hope that I can inspire others to do the same.

I think the biggest challenge I’ve faced so far is the imposter syndrome that comes along with being an artist. I know I’m not the only one who experiences it. I think it’s easy in today’s day and age with social media to lose sight of what actually matters when making art. I make art because it’s fun, and because I have a story to tell, and that is the only thing that matters. I grew up struggling with my mental health a lot, but music was always an escape for me. I just want to take the pain I go through in life and use it to create a world where myself and other like minded people can go to escape and celebrate what we’ve overcome together.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
If I had to recommend a few of my favorite spots, I love seeing shows at The Hotel Cafe, Desert Spot 5, The Troubadour, those are some of my favorite venues. I now help to curate a Nashville Style songwriters showcase called Writers Round LA in Ivanhoe started by the amazing Greg in Good Company. The environment reminds me a lot of the encouraging environment I grew up playing in, and was one of the first showcases I ever played in LA. I’m so proud to be a part of this community.

I also love Cornell Wine Company, I even wrote a song inspired by them called Ivy League!

Aside from venues, I’m a big fan of overlooks, and if you want a pretty view, just go drive down Stunt Rd for a bit. Those are my best recommendations.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I would like to dedicate my shoutout to my grandpa Mark Levy who passed away in March of last year. He taught me how to sing, even recorded me on cassette tapes at two years old! He’s the reason I moved to California, and is a huge part of who I am. I have his quote tattooed on my arm, “life ain’t straight up.” He taught me to roll with the punches, and to expect the unexpected! I carry his love and light with me everywhere I go.

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Other: Contact: baileydrewmusic@gmail.com

Image Credits
Pauline Vargas