Why I‘ll Never Make It

Broadway performer Katerina Papacostas joins the opening episode of Season 10! She has spent years of working in on tours, on Broadway, and across regional theatre. Currently appearing in the Tony Award–nominated revival of Chess, Kat recently stepped into the lead role of Florence Vassy, filling in for Lea Michele. In this conversation, Kat opens up about the realities of building a sustainable career in the arts — from survival jobs and burnout to leaving New York entirely and eventually becoming a software engineer while still pursuing performance. She shares how redefining success for herself created a healthier and more balanced creative life, both onstage and off. It’s an honest conversation about persistence, reinvention, and what it really takes to stay in the game long enough for opportunities to arrive. -- Why I’ll Never Make It was recently selected by MillionPodcasts as one of the Top 70 Musical Theatre Podcasts on the web (2026 Edition). This podcast is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices

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. But due to various factors that show never ended up coming to New York. Nonetheless, Christine was so great in that show. And she brought that same energy and vocal power to the role of Donna in Mamma Mia as well. The second leading lady I got to see was also someone I had worked with before in 42nd Street at Goodspeed in Connecticut. Now, she wasn’t making her Broadway debut, but she was playing a character for the first time: Roxie Hart in the long-running musical Chicago. She has about another month in this role, and so to celebrate her fantastic performance in the show I thought I would replay my conversation from 2022 with this dynamic leading lady...Kate Baldwin --- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices

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. She shows actors how to become clearer, more intentional collaborators in the room and more viable professionals outside of it. Together we talk about her years as a casting director and the creation of The Actor’s Green Room, where she worked closely with actors in person. This eventually morphed into the online space and the leap to fully digital training with the creation of the 2% Signature System. Jen also gives her honest and sometimes controversial assessment of education, access, and the cost of becoming a more bookable professional. Jen’s insights show us why some actors keep getting called in, keep getting trusted, and keep getting hired. And as a special treat, you get my full conversation with Jen in one single episode, something normally reserved for subscribers, that include auditions stories and the Final Five questions. --- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices

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. It’s where we hear about personal lessons, hopes for the industry, and those moments that truly define an artist’s career. --- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices

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. I share what’s been going on, why the silence stretched longer than I wanted, and how grateful I am for the patience and support of this community as I get things back on track. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. What started as a 25-day protest in San Francisco became a landmark moment in history, paving the way for the Americans with Disabilities Act. Abbie and Mason share what drew them to musicalize this event and how they balance storytelling and activism in telling such an important story. We also talk about the ongoing challenges of accessibility within theater itself — from a festival that couldn’t accommodate their actors to the irony of competing for a grant against their own mentor. Through it all, their journey reflects the very message of their show: that change takes persistence, collaboration, and a little bit of creative rebellion. --- Why I’ll Never Make It is an independent production of WINMI Media and Patrick Oliver Jones. To support the ongoing efforts of this podcast please ⁠subscribe⁠⁠ or ⁠⁠donate⁠⁠. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Matt Zambrano was the very first guest on the podcast. He and I did Man of La Mancha together in Orlando. Dan Domingues is a NY actor who took part in my Spotlight episode on Only Make Believe, a nonprofit that brings interactive theater into children’s hospitals and cafe facilities. They both share insights about the work they do as well as very personal feelings about their own ethnicity and heritage. In this episode as well as the Spanish one, there are no back and forth questions from me. In fact, I’ve done very little editing to these recordings, just cleaning up sound quality as much as possible and structuring these episodes together. But in general, I’m simply stepping back to let previous guests tell their own story, and say what THEY want to say. --- To get early access to full conversations, please become a ⁠⁠subscriber⁠⁠⁠ . And to support the ongoing efforts of this podcast you can also⁠ ⁠⁠donate⁠⁠ as well. Thank you! Learn more about your ad choices. Visit megaphone.fm/adchoices