In 1986, Oslin decided to make a final effort to regain a recording contract. She borrowed seven thousand dollars from her aunt, lost 40 pounds, rented a Nashville nightclub and invited record executives to a one-time music showcase. "The next morning, I sat waiting for the phone to ring. It did not," she recounted. Yet, through her connections, Oslin contacted Nashville producer Harold Shedd, who had recently been successful recording Alabama. Shedd convinced Oslin to record three of her original tunes and he eventually became her full-time production collaborator. She also met RCA Records executive Joe Galante in 1986. Galante believed Oslin had potential and signed her to RCA in 1986 when Oslin was 45 years old.