“Lucky To Be,” Willie Nelson & Trusting the Journey | Lily Meola
Singer-songwriter Lily Meola joined Heart of the Gulch host Tony Mendoza during CMA Fest 2026 to talk about her debut album Lucky To Be, the long road that led to finally releasing it, and what she's learned from touring alongside Willie Nelson.
After years of writing, recording and figuring out exactly what she wanted her first full-length project to sound like, Lily has arrived at an album that feels unmistakably her own.
Singer-songwriter Lily Meola during her Heart of the Gulch interview at CMA Fest 2026 in Nashville, Tennessee.
The Long Road to Lucky To Be
A debut album is supposed to introduce an artist.
For Lily, getting to that introduction took time.
She opens up about the years-long process behind Lucky To Be and why she was willing to wait until she had a collection of songs that truly represented who she wanted to be as an artist.
Rather than rushing to release a full-length project, Lily learned to trust her instincts and let the album take shape naturally.
The result is a record she describes as the truest version of herself yet.
Touring With Willie Nelson
One of the most remarkable parts of Lily's story is her relationship with Willie Nelson.
Touring alongside one of country music's most legendary artists has given her a front-row seat to not only Willie's performances, but the way he approaches music, audiences and life.
Lily reflects on performing for Willie Nelson's fans and what she's learned simply by watching a career built across generations.
She's also had the opportunity to perform a duet with Willie, creating the kind of career moment that's difficult to forget.
The Story Behind “Bolo Blues”
Throughout Lucky To Be, Lily pulls inspiration from real experiences.
That includes “Bolo Blues,” one of the songs she breaks down during her Heart of the Gulch conversation.
For Lily, songwriting is often about recognizing an experience worth capturing and then finding the right people to help turn that idea into a finished song.
Collaboration remains an important part of that process, but she's also become more confident in trusting her own creative instincts.
Tony Mendoza, host of Heart of the Gulch, interviews Lily Meola about Lucky To Be, touring with Willie Nelson, songwriting and her journey to releasing her debut album.
“Sleeping With My Boots On” Changed the Album
Sometimes one song can help an artist understand an entire project differently.
For Lily, “Sleeping With My Boots On” became one of those songs.
She explains how the track helped shift the direction of Lucky To Be and brought the album closer to the sound she'd been searching for.
It became another step toward creating a debut that wasn't simply a collection of songs—but a reflection of who Lily Meola actually is.
Learning to Trust the Journey
Releasing a debut album doesn't erase uncertainty.
Lily speaks candidly about impostor syndrome, self-doubt and learning to trust the path she's on.
It's something many artists experience while trying to measure their progress against everyone around them.
But after years of writing, waiting and developing her sound, Lily can finally look at Lucky To Be as proof of that progress.
She even considers what the 15-year-old version of herself would think about where music has taken her today.
From touring with Willie Nelson to releasing her first full-length album, the answer is probably pretty simple:
She'd be proud.
Lily Meola joins Heart of the Gulch to discuss her debut album Lucky To Be, touring with Willie Nelson, “Bolo Blues” and “Sleeping With My Boots On.”
What's Next for Lily Meola
With Lucky To Be officially introducing this version of Lily Meola to listeners, she's ready to take the songs beyond the record.
New tour dates, live performances and another chapter of songwriting are ahead.
But after spending years trying to make the debut album she knew she had in her, there's also something worth appreciating about finally arriving at this moment.
Lily Meola isn't rushing anymore.
She's learning to trust the journey—and maybe realizing she's pretty lucky to be on it.
Watch Lily Meola on Heart of the Gulch
Watch the full Lily Meola interview from CMA Fest 2026 as she joins Tony Mendoza to discuss Lucky To Be, touring and performing with Willie Nelson, “Bolo Blues,” “Sleeping With My Boots On,” songwriting and overcoming self-doubt.
Interview Chapters
0:00 — Lily Meola Interview | CMA Fest 2026
0:44 — The Story Behind Lucky To Be
1:57 — Why Lily Meola Waited to Release Her Debut Album
2:42 — Touring with Willie Nelson & Learning from a Legend
3:40 — What It's Like Performing for Willie Nelson's Fans
4:35 — Lily Meola's Favorite Part of Making Music
5:48 — Songwriting, Collaboration & Creative Process
6:23 — The Story Behind “Bolo Blues”
7:35 — What 15-Year-Old Lily Would Think Today
8:18 — “Sleeping With My Boots On” & The Song That Changed the Album
9:39 — Overcoming Impostor Syndrome & Trusting the Journey
10:45 — New Tour Dates, Lucky To Be & What's Next
Tony Mendoza is the Nashville-based host and creator of Heart of the Gulch, featuring conversations with country artists, songwriters and personalities from Nashville and beyond.
