Why I‘ll Never Make It Podcast
The actor’s journey is one of occasional highs and frequent lows. It is a path riddled with self-doubt and frustration as we question our career choices, wondering if we’ll ever really ”make it.” But it is those few moments of glory on stage or screen that can sustain us through all the setbacks and challenges. On this award-winning podcast, New York actor Patrick Oliver Jones invites fellow creatives to share three stories that offer a behind-the-scenes look at the creative life rarely seen in the glitz and glam of this industry. These conversations remind us we’re not alone in this often bumpy and winding journey of the performing arts.
FINAL FIVE: Kevin Munhall, Performer and Coach
Kevin Munhall back for the "Final 5 Questions," diving into wild survival gigs, redefining success in the arts, and the importance of self-knowledge over outside advice. Kevin Munhall also shares why his unique coaching program is a love letter to his younger self, and both reflect on how performers can build lasting, joyful careers. --- 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
Kevin Munhall Helps Actors Manage Stress, Anxiety, and Burnout
Kevin Munhall made his Broadway debut in Anything Goes at the tender age of 22 after just 6 weeks of being in NYC. But then, it would be almost 5 yrs till his second Broadway show. And then later on ,there was an injury which forced him to reconsider his own hopes and aspirations and discover what he really wanted, so he took a break from stage work for several years, only returning to the stage in Damn Yankees just last year. During his time away he trained in Somatic Education, Functional Breathing, Alexander Technique, Breathwork, Stress, Sleep & Respiration Physiology, and Nervous System Regulation. Armed with this knowledge, he began helping performers and even the muggles in the corporate world to manage stress, anxiety, and burnout. In our conversation, Kevin shares how that dream debut left him exhausted and even convinced him something was wrong with him. We talk about that shoulder injury that eventually led him to leave the Dirty Dancing tour. And we discuss what anxiety and stress do to our physical and mental health, and how often the goals we chase are not the things that will ultimately fulfill our lives or careers. Kevin’s program and content: habitdisruption.com His Instagram: @kevin_munhall --- 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
FINAL FIVE: Sydney Kane, Comedic Actress and Writer
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
Sydney Kane Brings Laughter to Her Life and Acting Career
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. --- 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
FINAL FIVE: Rachel Lin, Embracing Uncertainty and Trusting the Journey
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
Rachel Lin Brings Asian Representation to Law & Order and Creates Her Own Work
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
FINAL FIVE: New York Theater Company with Katherine Winter, Josh Zacher, and John Kroft
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
New York Theatre Company Takes Performance Off the Stage and Into the Streets
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
FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon
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
Michael Kostroff Sees Performing as a Calling and Everyday He Answers That Call
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
FINAL FIVE: Katerina Papacostas, Chess on Broadway
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
Katerina Papacostas Is Making All the Right Moves in Chess on Broadway
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
A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater
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
A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments
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
A Look Back at Ann Harada and Finding Longevity as an Actor
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
A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor
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
A Look Back at Misha Osherovich and Breaking Free from Body Image Pressures in Theater
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
A Look Back at Sharon Catherine Brown and a Legacy of Passion and Joy for Theater
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
A Look Back at Anthony Rapp, From The Little Prince to Seasons of Love
Since making my Broadway debut in Beetlejuice last year, I’ve spent a lot of time thinking about what it actually means to “make it” in this business. It took me twenty years from my first Broadway audition to finally getting that credit, with plenty of near misses along the way. But imagine being just ten years old and moving to New York City with your family for your Broadway debut…only to have the show close during previews. That’s exactly what happened to Anthony Rapp. Recorded in 2022 as the theater industry was finding its footing again after the COVID shutdown, our conversation goes far beyond the role many people know him for—Mark in Rent. Anthony reflects on that almost Broadway debut, the reality of film producers who didn’t want to cast him, and how he navigated the loss of two people closest to him. You’ll also hear a bonus segment about his time playing the title role in You’re a Good Man, Charlie Brown. Correction: In the episode introduction, I mistakenly referred to Anthony Rapp as playing Roger in Rent. Anthony actually originated the role of Mark Cohen on Broadway. Also, with it being mentioned during the episode, Anthony’s answers to the Final Five Questions can also be found here. Follow Anthony: IMDb / IBDB / Instagram Learn more about your ad choices. Visit megaphone.fm/adchoices
A Look Back at Lisa Howard 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. She is so spirited and cheerful, and that’s reason enough to love this conversation. But what made it so memorable is how she pulls the curtain way back and reveals the trials and tribulations of putting a new show together, some more successfully than others. Because for nearly twenty years, Lisa Howard has made a career out of originating roles on Broadway from The 25th Annual Putnam County Spelling Bee to 9 to 5 and Escape to Margaritaville. She shares what it’s like to survive a rehearsal process that feels impossible, to be part of a show the cast loves even when the critics don’t, and to help shape a piece of theatre while it’s still trying to figure out what it is. And then we discuss a topic everyone asks her about, but this time in a way that lets her define the story for herself. Follow Lisa: Website / IBDB / Instagram Learn more about your ad choices. Visit megaphone.fm/adchoices
