Randy Goodrum, who had written Anne Murray's hit "You Needed Me
," wrote this with West's producer Brent Maher. In a Songfacts interview with Goodrum
, he said: "We were trying to fashion some sort of new sound for Dottie. And we had gotten to know Dottie and she was this sassy tongue-in-cheek southern woman with a real character to her voice. She was a good singer, but she had tons of character. So we thought, we've got to give her some meat on the bones here. We've got to go find some songs, and then write the ones we can't find. And that day that I wrote 'A Lesson In Leaving' with Brent. We were in my studio when I lived in Nashville the first time, and we were trying to write this ballad. I got up to go in the kitchen and Brent, while we were writing the ballad, kept doing this sort of mid-tempo funk beat on his legs. He was kind of slapping out a little beat, sort of as a nervous tic, I guess. I went into the kitchen, and I thought, Maybe we should just write that, whatever that is. So I came back and I said, 'Do that patting again on your legs.' So he started doing it, and I started messing around. I picked up a guitar instead of the piano, to try to break ties with everything we'd been doing that day. And I don't play guitar very much at all. So I started playing it in G. And on a guitar on the low E string, it only goes down to E. So the pattern was… started on G to E. It was (singing), "bum de bum bum bum bum bum… ba da bum bum bum bum." 'Cause it couldn't go down to a D. So that ended up being sort of the bass pattern for 'Lesson In Leaving.' And 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. And that ended up being the core of the sound we were trying to create for her. We did build around it. We did some really nice sort of intelligent ballads for her."