Why I‘ll Never Make It

Why I‘ll Never Make It

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.

Episodes

FINAL FIVE: Rachel Lin, Embracing Uncertainty and Trusting the Journey

August 3, 2026 • 8 mins
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 n...
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Rachel Lin Brings Asian Representation to Law & Order and Creates Her Own Work

July 24, 2026 • 53 mins
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 ac...
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FINAL FIVE: New York Theater Company with Katherine Winter, Josh Zacher, and John Kroft

July 3, 2026 • 26 mins
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. ...
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New York Theatre Company Takes Performance Off the Stage and Into the Streets

June 24, 2026 • 91 mins
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 nav...
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FINAL FIVE: Michael Kostroff, Actor in Dog Day Afternoon

June 19, 2026 • 12 mins
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 / Instag...
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Michael Kostroff Sees Performing as a Calling and Everyday He Answers That Call

June 12, 2026 • 52 mins
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, es...
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FINAL FIVE: Katerina Papacostas, Chess on Broadway

May 29, 2026 • 31 mins
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 int...
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Katerina Papacostas Is Making All the Right Moves in Chess on Broadway

May 27, 2026 • 76 mins
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 — f...
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A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater

May 1, 2026 • 68 mins
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 s...
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A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments

April 20, 2026 • 88 mins
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 p...
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A Look Back at Ann Harada and Finding Longevity as an Actor

April 13, 2026 • 68 mins
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 ha...
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A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor

April 3, 2026 • 92 mins
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 o...
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A Look Back at Misha Osherovich and Breaking Free from Body Image Pressures in Theater

March 25, 2026 • 66 mins
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. Reco...
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A Look Back at Sharon Catherine Brown and a Legacy of Passion and Joy for Theater

March 13, 2026 • 152 mins
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 S...
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A Look Back at Anthony Rapp, From The Little Prince to Seasons of Love

March 6, 2026 • 81 mins
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 c...
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A Look Back at Lisa Howard Defining Success on Her Own Terms in Broadway Musicals

February 20, 2026 • 72 mins
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 putt...
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A Look Back at Geoffrey Owens and the Dignity of Work Beyond Broadway and Television

February 13, 2026 • 86 mins
I think most of us actors hope to be in a hit Broadway show or a popular film or highly rated TV show. But for those actors lucky enough to be in one, it can sometimes be all you’re known for and all your other work either goes unnoticed or forgotten. For example, you’ll hear from Anthony Rapp in a few weeks, that even with all he’s done onscreen and onstage, for most of us he will forever be Mark in the Broadway ...
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A Look Back at John McGinty and His Persistence as a Deaf Actor on the Broadway Stage

February 6, 2026 • 59 mins
As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape the podcast and transformed a simple interview into a meaningful message for us all. This episode features John McGinty, a deaf actor who lost his hearing at a young age and initially headed toward a career in finance, but theater kept calling him back. In this conversation, he shares the realit...
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What Does “Making It” Even Mean? — A Look Back at Ten Conversations

February 2, 2026 • 4 mins
As Why I’ll Never Make It approaches its tenth season, this special retrospective looks back at ten conversations that helped shape this podcast in meaningful and profound ways. Since 2017, this has been a place to talk honestly about a career built on uncertainty, rejection, hope, and persistence. And over time, it’s become something far more personal than I ever expected—a place where success is never the most i...
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Kate Baldwin Finds Creative Purpose Beyond Just Performing (REWIND)

January 9, 2026 • 51 mins
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 ...
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