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The wonderful Sydney Kane is back to answer the Final Five Questions and share some memorable auditions stories. This is a continuation of our previous conversation, an honest and humorous deep dive into her artistic journey. From memories of her first professional show to navigating the pressures of auditions and self-worth in the industry, Sydney Kane shares candid lessons and advice about authenticity, resilience, and creating community. 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

When the to-do list starts piling up, it’s easy to put off the things that matter most. After nearly six months of unemployment since my last show, I’ve found myself doing exactly that: staying up too late, sleeping in, snacking, spending an hour on a self-tape and then finding plenty of ways to avoid the rest of the day. Self-motivation and discipline have never come easily to me, while doing what’s comfortable can be all too easy. Then along comes Sydney Kane. An NYC-based actor, singer, comedian, and writer, Sydney has performed everywhere from off-off-off Broadway to the big 9x16 screen of a phone. She’s built a following with her insightful and hilarious takes on dating, while also creating her own opportunities as a writer and producer. In this episode, we talk about the limitations of college musical theater programs, why authenticity matters in your work, and what happens when you stop waiting for someone else to give you an opportunity. Sydney also shares the story behind Wife Material, her one-woman musical comedy special built from her own unfortunate dating decisions and featuring original songs. We talk about the vulnerability of turning personal experiences into art, the challenge of embracing your authentic voice, and why creating your own work can sometimes be the only way forward. Most of all, this conversation is a reminder to get off your butt and do something. Sometimes the artist you need to hear from is the one who gives you a swift kick in the pants. Follow Sydney: Website | Instagram | TikTok --- 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

Theater is a world of breakthrough performances and backstage challenges and is as cherished for its camaraderie as it is notorious for its pressures. After a wonderful initial conversation, Rachel Lin is back for an illuminating discussion, bringing her perspective as a creator, collaborator, and relentless advocate for artists’ well-being. In this discussion she highlights stories and lessons that resonate with any artist navigating the highs and hardships of a creative life. Rachel shares her vision of “making it” in the theater, moving away from the glitz of star billing towards something far more lasting: belonging and artistic growth. And in a bold address of industry culture, she doesn’t shy away from calling for systemic change, asking for a theater world where the artists themselves are valued and not merely their output. She also speaks candidly about wrestling with impatience and learning to surrender to timing. WINMI Host Patrick Oliver Jones and Rachel find common ground in these shared challenges. Their candid dialogue calls for greater compassion in the industry, all the while reminding us that the journey is what truly shapes an artist, not the destination. --- 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

Actors today are expected to do far more than wait for the next audition. Increasingly, they're becoming writers, producers, directors, and creators of their own work. Rachel Lin has embraced all of those roles, but not without first overcoming expectations that her life should have taken a very different path. Rachel shares how growing up as a Chinese immigrant shaped both her identity and her career, from secretly applying to acting programs against her mother's wishes to navigating an industry where she rarely saw herself represented. She reflects on becoming the Law & Order franchise's first East Asian female detective, what that milestone meant, and why true progress still requires artists willing to tell their own stories. That philosophy ultimately led Rachel to create her acclaimed one-woman show, discovering along the way that no solo production is ever made alone. It's a conversation about representation, resilience, and why today's actors often have to become the architects of their own careers. Follow Rachel: Website / IMDb / Instagram / Vimeo --- 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

Katherine Winter, Josh Zacher, and John Kroft from the New York Theater Company are back for an honest, insightful, and often humorous exploration of what it truly takes to carve out a meaningful career in the performing arts. Listen as these talented artists share their most memorable—and sometimes unconventional—survival jobs, from guiding Central Park tours to working in a wine shop and teaching at a ballet school. They open up about the twists, turns, and unexpected moments that have shaped their journeys, offering heartfelt advice to their younger selves and redefining what "making it" really means. If you've ever wondered how theater professionals stay grounded, why collaboration matters, or what personal growth looks like behind the scenes, these artists offer valuable lessons, industry insights, and inspiration for persevering—even when the spotlight feels far away. Follow NYTC: Website / Instagram / The Circuit --- 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

Step behind the scenes of the innovative New York Theatre Company with Katherine Winter, Josh Zacher, and John Kroft—the creative team behind their latest groundbreaking production, the immersive outdoor dance experience The Circuit. Katherine draws inspiration from classic Hollywood and Barbra Streisand as well as her Toronto theater roots. Josh believes movement is the heartbeat of storytelling, and John has learned to navigate the highs and lows of the industry—like being fired from a dream job. The trio also share candid stories about guerrilla theater, crowd-wrangling challenges, silent disco technology, and the drive to make NYC itself a living, breathing scene partner. Hear firsthand how these young artists are redefining the boundaries of live performance, even amidst pandemic setbacks and personal setbacks from lost agents to creative differences. Whether you're a Broadway fan, aspiring artist, or looking for new things to do in New York City, this episode is packed with practical insights on building community, producing immersive theater, and pushing art outside the box. It's an inspiring look at what it takes to make theater—and the lessons learned when things don't go as planned. Learn more: New York Theatre Company / The Circuit --- 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

Showbiz is full of uncertainty, self-doubt, and surprising moments of joy, a reality that even the most seasoned actors face long after their Broadway debuts. In this episode, celebrated stage and screen actor Michael Kostroff returns for a refreshingly honest and uplifting conversation—no roles, no scripts, just the real story behind his journey in entertainment. Follow Michael: IMDb / IBDB / Instagram 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

What does it really take to build a lasting career as an actor? For Michael Kostroff, the answer is persistence. Michael was actually one of the first guests to ever come on this podcast, and throughout this 10th season, you’ll get to hear from a few returning guests as they share lessons and experiences they’ve had since that initial appearance. Known to many audiences from Broadway, national tours, and television, especially his memorable role on HBO's The Wire, Michael shares the winding path of a career that has spanned decades. From his first professional contract at the Lawrence Welk Dinner Theatre to what he jokingly describes as having two Broadway debuts, Michael reflects on the opportunities, disappointments, and unexpected turns that shaped his journey. He also shares the story of landing a role in the new Broadway production of Dog Day Afternoon at the exact moment he was preparing to move his life to Canada. The conversation also revisits one of the defining experiences of Michael's career: the first national tour of The Producers. He explains why playing Max Bialystock became one of the most challenging and rewarding roles of his life, and how persistence over the years has continued to shape him as a performer. Follow Michael: IMDb / IBDB / Instagram --- 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 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

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

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

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

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

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

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