Episodes

  • FINAL FIVE: Katerina Papacostas, Chess on Broadway

    FINAL FIVE: Katerina Papacostas, Chess on Broadway
    May 29 2026
    In the previous episode, you heard stories from Katerina Papacostas, where we got into her theater experiences as a 19-year-old as well as her current show, Chess, and filling in for the lead role of Florence Vassy. But there’s more to uncover! And she’s back to answer the Final Five Questions, but first we have an audition story, when Kat was in final callbacks for a Broadway show. And this of course leads us into one my favorite subjects, self-tapes.went in for the role of Nicola in Kinky Boots. -- 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
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    32 mins
  • Katerina Papacostas Is Making All the Right Moves in Chess on Broadway

    Katerina Papacostas Is Making All the Right Moves in Chess on Broadway
    May 28 2026
    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
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    1 hr and 16 mins
  • A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater

    A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater
    May 1 2026
    As actors, it’s easy to get caught up in auditions, roles, and the day-to-day work of performing, often without stepping back to consider the larger forces shaping the stories we’re asked to tell. Playwright Lynn Nottage operates on that larger scale. A two-time Pulitzer Prize winner and one of the most influential voices in American theater, Lynn has built a body of work that challenges audiences while expanding what stories are seen and heard on Broadway and beyond. In this conversation, recorded in 2024, Lynn speaks candidly about the responsibility of storytelling, the discipline behind the writing process, and the long road to trusting a creative voice in an ever-evolving industry. From Ruined, which explores the lives of women during the civil war in the Democratic Republic of Congo, to the Tony Award-winning musical MJ, Lynn discusses the balance between artistry, ethics, and collaboration in theater. What emerges is a clear and grounded perspective on what it means to create meaningful work—not for recognition, but with intention. For anyone working in the performing arts, whether onstage or behind the scenes, this conversation offers a deeper understanding of how stories are shaped, and why the ones that matter most are often the hardest to tell. Follow Lynn: Website / Instagram / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 8 mins
  • A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments

    A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments
    Apr 20 2026
    Identity can feel like a moving target in the performing arts—something shaped not only by the roles actors play on stage, but by the expectations placed on them offstage as well. In this episode, recorded in 2019 at the Muny in St. Louis, J. Harrison Ghee and Caroline Bowman sit down to talk about navigating that balance in a career built on visibility. From starring in productions like Kinky Boots, Evita, and Wicked, both performers share what it means to take on iconic roles while also staying grounded in a sense of self within the world of Broadway, musical theater, and the larger performing arts industry. Looking back now, this conversation captures a moment before major milestones in each career—before Caroline Bowman took on the role of Elsa in the Frozen national tour, and before J. Harrison Ghee won a Tony Award for Some Like It Hot. What comes through is a candid and thoughtful discussion about identity, vulnerability, criticism, and the pressure to fit into categories, both as actors and as people. It’s an honest look at the work it takes to show up fully, take risks, and build a life in theater without losing sight of who you are. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 28 mins
  • A Look Back at Ann Harada and Finding Longevity as an Actor

    A Look Back at Ann Harada and Finding Longevity as an Actor
    Apr 13 2026
    No matter what it is that initially motivates someone to be in the arts, it could be the craft or the people or the fame, there is one thing I think we all strive for: longevity. Besides finding consistent work, which is certainly no small task, the foundation of a long career is figuring out what it takes to personally stay motivated, energized, and still be yourself over the years. Some days it can feel like you’ve got a handle on it, while other days it’s a scramble to keep priorities straight and maintain direction. I sat down with Ann Harada in 2024 to talk about Broadway career that has spanned 4 decades, from the original production of M. Butterfly and the most recent revival of Into the Woods to her current Broadway show, Schmigadoon. But Ann would be the first to tell you that finding happiness and satisfaction in the acting business didn’t come quickly or easily for her. In our conversation, she talked about some lean years before Avenue Q made her a Broadway star as well as how she continued working hard and pushing herself both on and offstage. Follow Ann: Schmigadoon / Facebook / IMDb / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 8 mins
  • A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor

    A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor
    Apr 3 2026
    Rejection is a constant in this business, even when you’ve had success. Some days you take it in stride, other days it can really sink in deeper than you expect. I’ve had plenty of moments where I questioned whether I was on the right path, wondering if I should leave New York or perhaps find another career altogether. At times it has been a real challenge to balance hope with reality. And there was no clearer example of that, for all of us, than during the Covid shutdowns. That’s when I met actress and singer Adrienne Walker and asked her to come on the podcast. She's appeared on Broadway in The Lion King and Kiss Me, Kate as well as the Dirty Dancing national tour. It’s hard to believe that it was five years ago—in the midst of our industry being turned upside down—that she and I sat down and talked about finding purpose as actors and the determination to keep going. That’s something that remains an issue even after the pandemic. Whether professional projects or personal goals, whatever comes her way, Adrienne handles the ups and downs with perseverance and humor. She shows us that resilience isn’t some grand gesture, it’s the steady, everyday choices that make the difference. -- Watch Now You See Me, Now You Don't from the New Works Virtual Festival in 2020. Follow Adrienne: Website / Instagram / IMDB / 32 Bar Cut Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 33 mins
  • A Look Back at Misha Osherovich and Breaking Free from Body Image Pressures in Theater

    A Look Back at Misha Osherovich and Breaking Free from Body Image Pressures in Theater
    Mar 26 2026
    After seeing Misha Osherovich in an Off-Broadway production of A Clockwork Orange, I began following Misha’s work and perspective online. A couple of years later, a deeply personal post about body image and eating disorder struggles stopped me in my tracks—speaking to something many of us face in this industry but don’t always say out loud. That moment led me to reach out, and eventually to this conversation. Recorded in 2019, this episode explores the pressures performers face when it comes to appearance, self-worth, and the constant scrutiny of both the industry and ourselves. What follows is one of the most candid and compassionate conversations I’ve had on the podcast. Misha Osherovich opens up about mental health, personal fears, and the work of separating identity from external validation, all with a level of honesty that is both unflinching and deeply empathetic. It’s a reminder that the most meaningful work often begins with telling the truth about lived experiences—and having the courage to share that truth. (Note: at the time of this interview in 2019, Misha Osherovich was using he/him pronouns but now identifies as non-binary, using they/she.) Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 7 mins
  • A Look Back at Sharon Catherine Brown and a Legacy of Passion and Joy for Theater

    A Look Back at Sharon Catherine Brown and a Legacy of Passion and Joy for Theater
    Mar 13 2026
    Growing up, it was my mother who sang in the church choir about the time I was joining the children’s choir, and my aunt spent her young adult years performing as a jazz singer. But I’m actually the first in my family to pursue a full-time career in theater. That gave me a certain freedom to find my own way through the industry, but it also meant navigating a path no one in my family had taken before. For artists like Sharon Catherine Brown, though, there’s a different experience entirely—one shaped by a legacy of performers who came before. While she has worked in television and film, theater has always been her first love, with numerous Broadway and national tour credits, including her current run on the road with The Notebook national tour. Sharon joined the podcast back in 2023 to talk about following in the footsteps of her talented family and honoring the profound influence they’ve had on her life and career. I also had the joy of working with her in the summer of 2022 at Goodspeed Musicals in Connecticut on a new musical adaptation of Anne of Green Gables. As Anne herself might say, Sharon quickly became a kindred spirit in my life—and as you’ll hear, we truly enjoy each other’s company. In fact, our conversation lasted more than three and a half hours. When it was first released, I split it into two episodes, with the Final Five Questions available only to subscribers. For this Look Back episode, I’m bringing the entire conversation together in one place—lightly edited, but still full of the heart, wisdom, and passion Sharone shares so generously. Learn more about Sharon's connection to her father, Johnny Brown⁠, and his career. Follow Sharon: Instagram / IMDb / IBDB Learn more about your ad choices. Visit megaphone.fm/adchoices
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    2 hrs and 33 mins