John Mayer first performed I Guess I Just Feel Like on iHeartRadio on Wednesday October 24th 2018. However, the song was officially released four months later, on February 22nd 2019.

On Instagram Mayer stated:

“I Guess I Just Feel Like” is the “get small and tell the truth” I mentioned a few weeks ago. Playing this song last night was one of the best calls I’ve made in a while. Your reactions have made the weeks of working these feelings out well worth it. Conversations have begun on how and when to get an “official” version out (it’s almost done) but I kind of love pointing you to new music that’s raw and not tuned and doesn’t make anybody any money. I dunno. Thank you.