Songfacts®:

• Jo Dee Messina's "Lesson In Leavin'" is a cover of Dottie West's 1980 #1 Country hit "A Lesson In Leaving." Messina released her version in 1998; it went to #2 and introduced the song to a new generation.
• "Lesson In Leavin'" is a sassy song that's right in Jo Dee Messina's wheelhouse as an independent woman who won't tollerate disrespect. It finds her putting a man with wandering ways on notice, letting him knew he's going to get a lesson. It was released on her second album, I'm Alright, which includes three #1 Country hits: "Bye Bye," "Stand Beside Me" and the title track.
• The song was written by Randy Goodrum along with Dottie West's producer, Brent Maher. For West, who often recorded ballads, it was a new sound, and the song became her first #1 Country hit. Regarding the lyric, Goodrum told Songfacts: "We thought about Dottie, we imagined her standing in the back door with a frying pan in her hand and a wink in the eye, and a tongue in the cheek, and the song just sort of fell onto the page. In about an hour, maybe, we had the whole thing pretty much written. We took that to Dottie and she just flipped out."
• Tim McGraw co-produced the I'm Alright album and had the idea for Jo Dee Messina to cover the song. Messina's version serves as a tribute to Dottie West, who was just 58 when she died in a car accident in 1991.
• It was Lonestar's "Amazed" that kept "Lesson In Leavin'" out of the top spot on the Country chart... for eight weeks. "There's a little scab on my soul from that one!" Messina said on the Off The Record Podcast.