by brad hart
For Frankie Errington (they/them), stepping into the role of J. Pierrepont Finch isn’t just about leading a classic musical; it’s about returning to a place that has witnessed their growth, both as an artist and as a person.
In San Diego Musical Theatre’s upcoming production of How to Succeed in Business Without Really Trying, Errington finds themselves at the center of a story about ambition, confidence and perception — timeless themes that resonate deeply in the present moment.
Frankie Errington approaches Finch not as a caricature of success, but as a figure whose journey highlights the absurdity of systems that reward style over substance. While Finch seems to glide effortlessly up the corporate ladder, Errington’s own path has been rooted in persistence and self-discovery.
Theater, they note, exists at the intersection of hard work, luck and timing, with no shortcuts guaranteed. That contrast — between Finch’s ease and an artist’s reality — adds an unexpected layer of authenticity to their performance.
This production also marks a meaningful return to SDMT for Errington, who last appeared with the company in 2019’s Sister Act. Coming back now feels distinctly different. In the years since, Errington has shown up to auditions — and life — with different headshots, different pronouns and a deeper understanding of who they are. Stepping into a leading role on the same stage where earlier versions of themselves once stood is less about revisiting the past and more about honoring growth.
The environment surrounding that growth matters. Errington speaks openly about the importance of chosen family within the theater world and beyond. A production, they say, is built collectively by cast members, understudies, designers, crew and box office staff working in constant collaboration.
Just as essential are the people outside the rehearsal room: the friends who remind you to rest, the loved ones who hold your opening-night flowers, and the voices that quietly insist you keep going. For queer artists, chosen family isn’t simply supportive; it’s foundational.
Away from the stage, Errington prioritizes rest and reconnection. Theater is a physical and emotional endeavor, and recovery is key. Sleep is sacred. Long walks offer a chance to reset, inspired by Mary Oliver’s poetry and the grounding act of noticing the world again. Sketching for joy, FaceTiming friends, and doting on other people’s pets round out the rituals that help Errington recharge.
As SDMT opens its 2026 season, Frankie Errington’s turn as Finch places an artist firmly in the spotlight at a moment that feels both earned and timely. With its lively score, physical comedy and satirical edge, How to Succeed in Business Without Really Trying provides the perfect framework for a performance shaped by reflection, humor and heart. Inviting audiences not just to laugh, but to see the climb from a new perspective.
Sidebar: A Classic with Staying Power
Premiering on Broadway in 1961, How to Succeed in Business Without Really Trying quickly became a cultural phenomenon, winning seven Tony Awards, including Best Musical. Based on Shepherd Mead’s satirical self-help book, the show later inspired a 1967 film starring Robert Morse, who also originated the role of J. Pierrepont Finch on stage.
Over the years, the musical has continued to evolve, with women and nonbinary performers stepping into the traditionally male role of Finch in regional and reimagined productions. This has offered fresh, contemporary perspectives on ambition, power, and workplace culture.
With iconic songs like “I Believe in You” and “Brotherhood of Man,” its clever score and biting humor still resonate. And despite its Mad Men–era suits and martini lunches, the show’s commentary remains surprisingly and sometimes alarmingly relevant.
How to Succeed in Business Without Really Trying is now on stage through March 1 at San Diego Musical Theatre. sdmt.org