Katerina Papacostas Is Making All the Right Moves in Chess on Broadway

About this episode

Katerina Papacostas discusses her journey in the arts, the challenges of building a sustainable career, and her recent role in the Broadway revival of Chess.

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…

People in this episode

Host: Patrick Oliver Jones

Guest: Katerina Papacostas

Topics covered

• Broadway
• performing arts
• career sustainability
• reinvention
• persistence
• theatre

Keywords

• Broadway
• Katerina Papacostas
• Chess
• career
• performing arts
• reinvention
• Tony Award
• sustainability
• burnout

Mentioned in this episode

Organizations: WINMI Media, MillionPodcasts

Books & works: Chess

More episodes of Why I‘ll Never Make It

• FINAL FIVE: Katerina Papacostas, Chess on Broadway · May 29, 2026 · 32 min
• A Look Back at Lynn Nottage Shaping Stories That Matter in American Theater · May 1, 2026 · 1h 8m
• A Look Back at J. Harrison Ghee & Caroline Bowman Before the Breakthrough Moments · April 20, 2026 · 1h 28m
• A Look Back at Ann Harada and Finding Longevity as an Actor · April 13, 2026 · 1h 8m
• A Look Back at Adrienne Walker Navigating Rejection as a Broadway Actor · April 3, 2026 · 1h 33m
• A Look Back at Misha Osherovich and Breaking Free from Body Image Pressures in Theater · March 26, 2026 · 1h 7m