Freewheelin' Woman

Jewel recorded the album live with a band and was partly inspired by famous R&B and soul records made in Muscle Shoals, Alabama, with the artist stating, "I cut my teeth on singers like Ella Fitzgerald, Dusty Springfield, and Sarah Vaughan and got into those Muscle Shoals records a little later on, and for some reason that's where my voice and my writing wanted to go on this album".[3]

Regarding the musical diversity, Jewel explained that "the record is definitely showing influences I haven't been able to pay homage to before" and added, "I always have thousands of songs in my back catalog, and so I was always able to just instantly have at least ten songs that I was going to use for a record in any genre" but that "It's the first time I ever challenged myself to write a record from scratch. I wanted it to be exactly who and where I was now". When discussing the gap between Picking Up the Pieces and Freewheelin' Woman, Jewel confessed that "I've always taken a lot of years between records when I feel like I need time to psychologically adjust or to creatively reload. I think writing, for me, evolves and changes. I have to have a lot of input. I like to read a lot. I like to experience a lot so I have new things to write about".[4]

In November 2019, Jewel released "No More Tears", her first new song in four years, for the soundtrack to Lost in America, a documentary by American filmmaker Rotimi Rainwater about youth homelessness, of which Jewel was an executive producer. Speaking to American Songwriter, she stated that she was inspired to write the track because she was moved by the stories of the individuals featured in the film and related those to her own experiences of being homeless when she was eighteen. In the same interview, it was confirmed that "No More Tears" would also be the first track from her upcoming album, which she hoped to release sometime in 2020.[5][6] A re-recorded version of the track, featuring country singer Darius Rucker, is included on Freewheelin' Woman.

"Grateful", the second single from the then as-yet untitled album, was released in April 2020. In an interview with Rolling Stone, Jewel expressed that the song was written about her experiences with anxiety and the crucial role that perception plays in processing your emotions, explaining that, "I learned that if I was headed into a panic attack, I could hack my way into a dilated state by focusing very hard on a different feeling. I chose gratitude. It's amazing how profound such a single thing can be if you feel it deeply enough. It's a practice I still use today. I'm pleased to release this new song inspired by the transformative capability of a simple feeling".[7]

On February 23, 2022, Jewel officially announced that her new album, titled Freewheelin' Woman, would be released on April 15. Alongside this announcement, she previewed the album's lead single, "Dancing Slow", which features American rock band Train, whom she would be supporting on their AM Gold Tour between June and August 2022.[8] In a statement about the track, Jewel explained that "Dancing Slow" is "ultimately about the ebb and flow of life and cherishing those moments of certainty that are shared when you're with a trusted companion. It feels like time slows down for a moment. I'm so glad Train was able to join me on this track, with Pat Monahan's sweet vocals adding another layer to the melody".[9]

The final pre-release track from the album, "Long Way 'Round", was shared in March 2022, with Jewel describing it as "a song about overcoming something difficult, even if it requires getting lost or taking the longer way around. I'm celebrating some of the things I've overcome as well as the choices I've made that have brought me to where I am today. The heart and mind are powerful muscles that are always willing to adapt and grow when you let them".[10]