Why I‘ll Never Make It

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!

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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

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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!

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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.

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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!

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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

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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!

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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

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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!

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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

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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!

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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

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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!

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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.

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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!

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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.

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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!

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