Why I‘ll Never Make It

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 teachin...

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,...

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 / Ins...

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 tou...

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 c...

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 c...

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...

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 Boo...

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...

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 w...

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 c...

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 bef...

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...

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 tr...

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...

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 conver...

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...

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...

Step inside the dressing room with Beetlejuice's Justin Collette for a behind-the-scenes conversation that’s equal parts bone broth and backstage banter. From the rock riffs of School of Rock to the undead hilarity of Beetlejuice, Justin shares his wild ride from Canadian improv star and punk band frontman to taking center stage on Broadway. We discuss his his technique of “farting with vocal cord...

Being an actor requires a constant balancing act between showing up creatively and understanding how the industry actually functions. And Jen Rudolph has spent years operating at the intersection of casting, coaching, and strategy. She shows actors how to become clearer, more intentional collaborators in the room and more viable professionals outside of it. Together we talk about her years as a ca...

Chicago is now celebrating 29 years on Broadway, with multiple national and international companies as well. And for more than two decades David Bushman has been a part of various Chicago productions around the world. But what makes David’s story remarkable isn’t just his longevity with the show—it’s the path that got him there. We talk about his early days in community theater, his unexpected mov...

The previous episode with Trisha Paytas covered so much ground, from her recent Broadway debut in Beetlejuice to her rise as a YouTube star. But one of the best parts of every conversation is when we get to discuss the Final Five Questions.  It’s where we hear about personal lessons, hopes for the industry, and those moments that truly define an artist’s career. --- Why I’ll Never Make It is an in...

Trisha Paytas joins the podcast to talk about her unexpected and much-talked-about Broadway debut in Beetlejuice. She shares what drew her to the show, how the opportunity came about, and what it’s been like stepping into a completely new kind of spotlight. We also get into her family background and the early days of her online career, how she first gained attention, and the twists and turns of tw...

In this brief update, I open up about the last several weeks—Broadway opening week, getting sick, and a recent injury—and how all of it pulled me away from releasing new episodes. I share what’s been going on, why the silence stretched longer than I wanted, and how grateful I am for the patience and support of this community as I get things back on track. Learn more about your ad choices. Visit me...

In the previous episode, Abbie Goldberg and Mason McDowell dove into their new musical 504 as well as the obstacles they’ve faced trying to produce their own works, and it was such an insightful conversation. But there’s still so much more to explore! That’s why I’m thrilled to have Abbie and Mason back here with me for the Final Five Questions—where we get a little more personal by uncovering les...