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Will Overman on Road Life and Traveling Songs

Tuesday, October 21, 2025 By Mayer Danzig

Will Overman (credit Joey Wharton)

Photo credit: Joey Wharton

Tell us about your tour vehicle. Any notable breakdown stories?

Funny you ask. I’m currently selling my Chevy 1500 Express I lovingly dubbed “Kacey”. I put roughly 120K on it and had to have the rear differential rebuilt about a year and a half ago which was a major setback. We’ve had to fix AC vacuum lines during South Carolina summers, I had the windshield gasket taped on with gaff tape for about a year, and both of the front door panels ripped completely off. But other than that, she’s been a valiant and trusty steed!

The reason I’m selling her is because these days I’m touring out of my Tacoma. Right now I do about 75% solo touring, which means I don’t need space for a band and I don’t have to pull a trailer. I’ve found that having a tour van is convenient in the sense of just hopping in and rolling, but the overhead of keeping it running well and the stress of that on the road often overrides any convenience. Besides, I love to fly fish and go on mini adventures when I’m on the road and the truck is a little easier to whip around than a full sized tour van.

How do you eat cheaply and/or healthy while on tour?

I don’t. I’m kidding. Maybe. No, but in all seriousness, I think this is one of the most challenging aspects of road life. Cheap and healthy aren’t neighbors. You can order a $15 salad on the road but you’ll be hungry in an hour and you don’t know when you’ll eat again. So I’ll often go for some kind of sandwich to kinda meet in the middle between salad and burger. Special shout out to Jersey Mike’s though, that Italian Sammy checks all the boxes for me. Number one road food by far. I’ve started packing a cooler with healthy snacks like apples, granola bars, etc. and that helps me spend less money on low quality food.

How many strings do you break in a typical year? How much does it cost to replace them?

I used to break a lot more. The Avett Brothers are one of my biggest musical influences and having watched Scott and Seth break 8 strings a show, well, I wanted to do the same thing. Then in my mid-twenties I realized that costs money. So I’d say I break a couple a year and I probably change my strings at least once a quarter. If I’m in a heavy tour cycle or I’m playing shows outdoors in dusty or salty environments I change them more.

A good pack of strings is about $15. So, it’s not cheap but as far as upkeep for my tools goes it’s an investment I’m happy to make.

Where do you rehearse?

Man, I’ve rehearsed in some weird spaces. The strangest ones always smell like stale cigarettes and light beer. I hold a certain space in Richmond, VA close to my heart. Let me set the scene for you. Cinderblock box. Painted black. No AC. It’s 98 degrees outside. It’s 102 inside. No acoustic treatment. Wall of amps. Box fans. Sweat. So much sweat. Yeah, that spot, that one’s my favorite. The other spots are usually just some space I’ve carved out in my house or a buddy’s. It’s never glorious, sure as hell isn’t sexy, and, if nothing else, it’s an absolute cluster of cords haphazardly flung across a grimy floor and a good hang.

What was the title and a sample lyric from the first song that you wrote?

Hmmmm, that’s a good question. I wrote some terrible songs when I first started out. Hell, I still write bad songs. They can’t all be good. But one of the first songs I wrote was called “Bryerson Hill”. Very, very Mumford leaning. It was about a guy, probably me, who liked to travel. I write a lot of traveling songs, shocker. But I think my favorite line is “Miss Tiffany sweeps the steps of the Roadhouse Inn while the man in the moon smiles with a grin”. No idea what’s going on here, who is Tiffany, where’s the Roadhouse Inn? I dunno, but I kinda dig it.

Describe your first gig.

First gig was probably singing “House of the Rising Sun” at my parents’ annual backyard oyster roast. If you’ve never heard a 12 year old singing about whores and booze, well, it’s something. First paid gig was at a venue in Virginia Beach called Thumb’s. Yes, Thumb’s, like the appendage. It was a weekly gig with my friend Mike “Elwood” Overcash. Mike had a lot of demons and is no longer with us but I learned a great deal from him and am so grateful for those strange late high school gigs. Surprisingly, Thumb’s didn’t make it.

What was your last day job? What was your favorite day job?

Ha, still working one brother! I wait tables at a restaurant in Nashville when I’m not on the road. The service industry, wow, man am I thankful for it. I’ve worked kitchens, I’ve worked coffee shops, I’ve waited tables and it’s all helped me pursue a career in music. It’s a grind, some days I hate it, others I don’t. But it affords me the life I lead and industry people are a special breed that I love to be around.

Favorite non-music day job. That’s a two parter. I do video/photo work on the side and used to work for a small production company in Charlottesville, VA. That was one of my all-time favorite jobs. Good people, creative work. Hard to beat. The other job that sits at the top was camp counselor. I went to and eventually worked at a small summer camp called Maxwelton in the mountains of Virginia. One of my favorite places on earth. Being outside all day, teaching shop, trying to help boys become good men. I felt a lot of purpose during that time in my life, hard to beat that.

How has your music-related income changed over the past 5-10 years? What do you expect it to look like 5-10 years from now?

In the last 5-10 years it’s been a roller coaster. I had some good sync years where I could proudly say I made my entire living off of music. Then those years came to an end. Since then it’s been a balancing act so many of us working musicians do: hitting the road then working a part time job when off the road. It’s a grind, and I hope it doesn’t last forever. I would like to sustain myself entirely from music but I’m just not there and I will have to diversity my income streams for the foreseeable future. 5-10 years, I’ll be 36 to 41 years old. I want to build a life. I want a home. I want stability. I want to provide for those I love. I want a damn dog. So, in short, I’d like to be in a place financially where I can do all those things while pursing my art at the same time.

What one thing do you know now that you had wished you knew when you started your career in music?

Christ almighty, there’s so much to unpack here. I’m gonna answer this in a roundabout way. I wish I knew it wasn’t just about talent. It’s heart, it’s raw talent, but less romantically, it’s also about money. So much of this industry runs on who has the most money to spend. And that has been a hard pill to swallow when you and many of your peers are working their asses off and then the young TikTok star with tons of financial backing flies past ya, that hurts. But, now here is the roundabout part, at the end of the day it’s still talent and heart. You can pump a million dollars into a song. That song is not a career, it is not a catalog to hang your hat on. I get the most fulfilled from writing a song I believe in, from putting on a show and knowing I left it all on the stage. Damn the numbers, damn the analytics, that’s never why I got into it. It’s about the art, and that is the lesson I’m talking about. I wish I knew it would take more than just heart and talent, but if you don’t have those things, it won’t mean a damn thing.

Will Overman is a Virginia raised singer-songwriter living in Nashville, TN. Often referred to as “Appalachian John Mayer,” Overman is known for his dynamic vocal delivery and heart-worn lyrics wrapped in a mixture of Alternative and Country music, that is as restless as the writer himself.

Working with producers Bobby Holland and Brad Sample, Overman’s sophomore album, Stranger (released September 26, 2025), finds the Virginia-raised singer-songwriter developing as both a storyteller and a musician. Singles such as “Held Up by a Woman,” “Virginia Is For Lovers” and “Names” build on his penchant for poetic lyrics bound by endlessly catchy tunes, and are a great representation of the energy that Will delivers live.

Connect with Overman online and on the road.

Filed Under: Interviews, Singer/Songwriter, Why It Matters Tagged With: Will Overman

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