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.

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Jess Woodland: @justjesswoodland

Matt Burrill: @raisedrowdymatt

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