Jenny Tolman on Chasing Dreams as a Mom, The Road & Honky Tonk Songs with Gretchen Wilson

Jenny Tolman joins That Nashville Girl for a rooftop conversation during CMA Fest that’s equal parts country music, motherhood, and unforgettable Nashville stories.

After introducing herself to a national audience on *The Road*—the Paramount+ series from Taylor Sheridan featuring Blake Shelton, Keith Urban, and Gretchen Wilson—Jenny shares what it was really like to leave her young son at home while chasing a lifelong dream.

She opens up about pumping on the road, balancing motherhood with a music career, and why those sacrifices made every moment on the show even more meaningful.

Jenny also reflects on the story behind her single “Baby Steps,” the unexpected support it received from Bobby Bones and Women of iHeartCountry, and why the song’s message of appreciating how far you’ve come resonates so deeply with her life today.

In this episode, Amanda and Jenny discuss:

• Jenny’s experience filming The Road
• Leaving her son for the first time while competing on national television
• The realities of motherhood in the music industry
• The story behind “Baby Steps” and its unexpected radio success
• Meeting her husband and producer, Dave Brainard
• The emotional inspiration for “Lonely in the Lone Star”
• Performing for the family of fallen Marine Riley McCollum
• Writing “Honky Tonk Songs” and collaborating with Gretchen Wilson
• What Jenny learned from Gretchen during The Road
• Cowgirls at the Cowboy, her all-female music festival in Jackson Hole
• What’s next for Jenny Tolman in 2026

From laugh-out-loud stories about finding love in Nashville to deeply personal conversations about grief, family, and resilience, this episode captures everything that makes country music so powerful.

It’s a conversation about chasing dreams, honoring the people who shape us, and remembering that life’s biggest milestones are often built one baby step at a time.

Listen to Jenny Tolman’s music, including “Baby Steps,” “Lonely in the Lone Star,” and “Honky Tonk Songs” featuring Gretchen Wilson. Be sure to follow her for tour dates and new music.

*Follow Jenny Tolman*
Instagram: @jennytolman
Website: www.jennytolman.com

*Follow That Nashville Girl*
Instagram: @thatnashvillegirl
Website: www.thatnashvillegirl.com

*Follow Amanda Adams*
Instagram: @askamandaadams

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