Jess Woodland: Taking the High Road Through Darkness & Finding Her Sound

On Episode 294 of Outside The Round, Matt Burrill sits down with Nashville native Jess Woodland. Fresh off the release of her EP High Road, Jess shares her journey from bluegrass roots and a rural Tennessee upbringing to carving out her own lane in today’s music scene. Jess opens up about stepping away from music, facing serious health challenges, and ultimately finding her way back with a renewed sense of purpose. She dives into the making of High Road, blending country, Americana, and alternative influences into a gritty, emotionally-driven sound that’s uniquely her own. The conversation also explores building a fanbase through social media, navigating the highs and lows of being an independent artist, and the importance of self-worth, community, and resilience. Jess’s story is a powerful reminder that sometimes the hardest path forward is the one worth taking. Follow on Social Media: Jess Woodland: @justjesswoodland Matt Burrill: @raisedrowdymatt Raised Rowdy: @raisedrowdy Outside The Round: @outsidetheround Chapters (00:00:00) - Harlem native on the ice storm(00:02:39) - Bluegrass singer-songwriter on his roots(00:04:43) - "You're Not Done" by Emeli(00:09:19) - All The High Roads, On Spotify(00:11:16) - What Kind of Music Do You Make?(00:14:41) - Singer-Songwriter talks about East Nashville(00:18:14) - Songwriters Round(00:19:06) - Alex Jones on How Old Does He Feel?(00:21:31) - Michael Pinto on His EP(00:24:25) - Tennesse rapper Becca Ray on coming out(00:28:00) - Rihonda on Love Yourself(00:30:33) - Michael on His Hardest Songs(00:34:24) - "Thank You For showing Me How I'm Lonely"(00:38:54) - 100. Playing One of Our Nights(00:39:12) - Michael Jackson on New Music(00:40:01) - Who Would Be Some Acts That I'd Love to Go Out With(00:43:35) - "You're the CEO of Your Business"(00:45:14) - What do we like doing when we're not on the music grind(00:48:01) - Can You Travel To All 50 States?(00:50:56) - Michael Jackson on His Daughter's Help(00:54:05) - Jess Woodland on Posting Her First Tik Tok Video