Why I‘ll Never Make It
Conversations with fellow creatives about their setbacks and struggles in the performing arts and what keeps them going.
All Episodes
A Look Back at Lisa Howard and Defining Success on Her Own Terms in Broadway Musicals
After working with Lisa Howard in 2022 on a production of 42nd Street at Goodspeed in Connecticut, she sat down with me the following year to chat about her career and of course reminisce about our time together doing that show.
A Look Back at Geoffrey Owens and the Dignity of Work Beyond Broadway and Television
I think most of us actors hope to be in a hit Broadway show or a popular film or highly rated TV show. But for those actors lucky enough to be in one, it can sometimes be all you’re known for and all your other work either goes unnoticed or forgotten.
A Look Back at John McGinty and His Persistence as a Deaf Actor on the Broadway Stage
As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape the podcast and transformed a simple interview into a meaningful message for us all.
What Does “Making It” Even Mean? — A Look Back at Ten Conversations
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.
Kate Baldwin Looks For Creative Purpose Beyond Just Performing (REWIND)
This past fall 2025 I got to see two of my favorite leading ladies on stage. The first was Christine Sherrill, who was making her Broadway debut in Mamma Mia. She and I had first worked together in the out-of-town tryout for First Wives Club back in 2015 that ran for about a month and a half in Chicago.
Justin Collette Brings Beetlejuice to Life at the Palace Theatre
Step inside the dressing room with Beetlejuice's Justin Collette for a behind-the-scenes conversation that’s equal parts bone broth and backstage banter. From the rock riffs of School of Rock to the undead hilarity of Beetlejuice, Justin shares his wild ride from Canadian improv star and punk band frontman to taking center stage on Broadway.
Jen Rudolph Helps Actors Focus on the Business of Acting
Being an actor requires a constant balancing act between showing up creatively and understanding how the industry actually functions. And Jen Rudolph has spent years operating at the intersection of casting, coaching, and strategy.
David Bushman Proves There’s No Expiration Date on a Theater Career
Chicago is now celebrating 29 years on Broadway, with multiple national and international companies as well. And for more than two decades David Bushman has been a part of various Chicago productions around the world.
FINAL FIVE: Trisha Paytas, YouTuber and Broadway Performer in Beetlejuice
The previous episode with Trisha Paytas covered so much ground, from her recent Broadway debut in Beetlejuice to her rise as a YouTube star. But one of the best parts of every conversation is when we get to discuss the Final Five Questions.
Trisha Paytas on Media, Missteps, and Making Her Broadway Debut
Trisha Paytas joins the podcast to talk about her unexpected and much-talked-about Broadway debut in Beetlejuice. She shares what drew her to the show, how the opportunity came about, and what it’s been like stepping into a completely new kind of spotlight.
Apologizing for My Own "Why I’ll Never Make It" Moment...
In this brief update, I open up about the last several weeks—Broadway opening week, getting sick, and a recent injury—and how all of it pulled me away from releasing new episodes.
FINAL FIVE: Abbie Goldberg & Mason McDowell, Musical Theater Writers
In the previous episode, Abbie Goldberg and Mason McDowell dove into their new musical 504 as well as the obstacles they’ve faced trying to produce their own works, and it was such an insightful conversation. But there’s still so much more to explore!
Abbie Goldberg and Mason McDowell Turn a Movement Into a Musical
Writers Abbie Goldberg and Mason McDowell are the creative team behind 504: The Musical — a new show inspired by the real-life 1977 sit-in that ignited the disability rights movement.
Historias Hispanas en Español - Bianca Marroquín, Luis Salgado y Mas (REWIND)
Bienvenidos y gracias por acompañarnos en esta edición especial de Why I’ll Never Make It! En esta segunda parte de mi serie sobre historias hispanas, escucharán a mis invitados anteriores compartir sus propias historias y experiencias en español.
Hispanic Stories in English - Matt Zambrano and Dan Domingues (REWIND)
As Hispanic Heritage Month comes to a close, I wanted to share a episode from 2020. This is part one in a series of former Hispanic guests of the podcast coming back to share their stories in their own words. The second part - la segunda parte - will be en español.
Audition Stories 2025 with Lynn Nottage, Aubie Merrylees, Elizabeth Hess, Simon Tam, and More!
It’s been several seasons since the last time Audition Stories took center stage, but they’re finally back — and this time with a brand-new collection of unforgettable moments from the audition room.
FINAL FIVE: Jennifer Apple, Actress and Founder of Empowered Artists Collective
Jennifer Apple returns for this bonus episode to tackle the Final Five Questions. From her very first professional show of Spring Awakening to the lessons she’s still learning today, Jennifer opens up about how she defines success, the advice she’d give her younger self, and the changes she hopes to see in the industry’s future.
Jennifer Apple Turns Setbacks Into Artistic Growth and Community
A serious back injury could have ended her career before it really began. Instead, it became the turning point that led to new opportunities—earning an MFA at ACT in San Francisco, training in Italy, and finding fresh ways to grow as a performer.
FINAL FIVE: Patricia McGregor, Artistic Director of New York Theater Workshop
Patricia McGregor’s first steps into the world of professional theater were marked by a sense of awe and a drive to make every moment matter.
Patricia McGregor on Making Bold, Tough Choices and Shaping the Future of Theater
Patricia McGregor’s journey to becoming artistic director of New York Theatre Workshop has been anything but linear. Growing up in the Virgin Islands, she and her sister created performances wherever they could, laying the foundation for a lifelong devotion to storytelling.
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