In Episode 149, Billy Donnelly re-enters a mental space from the past that he does not like being in: seeking acceptance and outside validation. He once again shares the story of his time as a writer and his desperate desire to be part of "The Cool Kids Club" of people whose stamp of approval would solidify him as someone of note in the community. That brings things to today when he found himself doing something similar with a new piece he had written recently and chasing something similar -- being acknowledged by those with influence within a different community. As a result, he examines why he so badly has wanted this form of acceptance, how it has made him feel over the years seemingly never getting it, and the growth he's made over time in at least being to acknowledge it for what it is and knowing how badly it affects his mental health.