As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape this podcast in meaningful and profound ways. Since 2017, this has been a place to talk honestly about a career built on uncertainty, rejection, hope, and persistence. And over time, it’s become something far more personal than I ever expected—a place where success is never the most interesting part of the story.

This revisit isn’t some “best of” series or a collection of the biggest names. These episodes feature artists who showed up with honesty and openness, sharing the setbacks, questions, and quiet work it takes to keep going. Across the next several weeks, you’ll hear voices like Anthony Rapp, J. Harrison Ghee, Ann Harada, Lynn Nottage, and others whose stories still resonate, reminding us why these conversations matter and why they’re worth hearing again as we head into season ten.

Learn more about your ad choices. Visit megaphone.fm/adchoices