In 2013 Seth Avett divorced his first wife Susan and some fans blamed his relationship with Dexter actress Jennifer Carpenter for the split. The co-frontman channeled his pain regarding the marital split into several of the songs on True Sadness, including the title track. "It's really just about resolution: coming to a place in your life where you can accept the great level of sadness that you're going to experience if you live into old age," explained Seth Avett to Billboard magazine. "It has been made very clear to us that we are like our audience, so it's not that vulnerable to talk about divorce, because a lot of people have gone through it. I feel very safe within the band."
The 2017 Judd Apatow-directed documentary May It Last: A Portrait of the Avett Brothers, follows the making of the album.
Eddie Vedder often changes the words when he sings "Yellow Ledbetter." The basic story is about a guy whose brother dies in the first Gulf War. Apparently, bad news in the army is given in yellow envelopes.