I work in the American theatre. I’m also a real estate agent. 

The first statement necessitates the second, as there are precious few roles in the American theatre that don’t require supplemental income, a side gig, a survival job. I’ve always made do with that trade-off, and I love both of my jobs. Even now, when my theatre job is one of the best there is—I am the executive director for Creative Affairs at the Dramatists Guild of America—I still maintain my real estate business, in part because I find that work meaningful, and in part because I want to be able to walk away from my beloved role at the guild when necessary. 

But what does “when necessary” look like? When is the right time to step aside and let new leadership take over? I’m lucky to have said goodbye before, so I hope to recognize my chance when it comes again.

In 1995, I produced the first iteration of the 24 Hour Plays™ (yes, it’s a registered trademark—I’m an IP nerd from way back) as one project among many for my fledgling production company, Crux. We handled production management for Off-Broadway companies to support our own creative work. The 24 Hour Plays was meant to be a one-time thing. 

Twenty-five years on, that “one-time thing” is now a vibrant force that has brought together creative communities around the world to make immediate live theatre and raised millions of dollars for charities. When Crux folded, as many small businesses do, my collaborators moved on to important work, informed by their own passions and the many lessons we learned together. I packed up my hard-won knowledge and pledged to keep the 24 Hour Plays going. 

In start-up culture, you’re encouraged to “fail fast”—to test new ideas and see if they work, then use what you learn to continue innovating. Many small businesses simply fail, fast. According to the Small Business Administration, only 50 percent of small businesses with employees make it to the five-year mark. (In addition to Crux, I co-founded a film production company called Blacklist Films, which failed as well. Running a small for-profit business in this country — particularly in New York City — is hard.) To keep the 24 Hour Plays alive, I formed a new nonprofit company with some smart pals who agreed to forgo salaries, office space, and any real infrastructure so we could channel our meager earnings back into the project. 

The nonprofit business structure allowed us to do just that. No payroll? No problem. We traveled the world, sharing our joyful practice with international peers. We produced the 24 Hour Plays in London, Dublin, Mexico City, Germany, Australia, and Finland, and all around the U.S. Everyone on our team was a volunteer, from the artists who participated to the folks who showed up to hang lights or run the sound board. The nonprofit business structure can support ongoing losses in a way other small businesses cannot. A generous donor can plug financial holes and a Hail Mary fundraising round can close an earned-income gap. We operated on that model for years. 

But we all got older. We had kids and we found fulfilling day jobs that demanded our time and attention. The 24 Hour Plays needed a new model, but we could not imagine how that might happen. I was ready to hand over the reins, but we were limping along on less than $30,000 a year—how could we hire someone to take over? 

As it turns out, the solution was within our organization already. Mark Armstrong had worked with us for years as a director, advisor, and producer of the 24 Hour Plays: Nationals. He agreed to give us a shot, taking over the company at a crucial point in its evolution. He built our small but mighty organization into a (still) small but now disproportionately influential sensation. From the 24 Hour Plays on Broadway and the 24 Hour Musicals to a free professional intensive for young artists, from licensed shows worldwide to the new, socially distanced phenomenon the 24 Hour Plays: Viral Monologues, more people in more places are enjoying (and participating in) the work of that little company than ever before. Throughout our shift into sustainability, my co-founders and I have been delighted to find that the original ethos of the organization still remains: The 24 Hour Plays “brand” remains one of joyful service, passionate collaboration, and fearless creativity.

Our small nonprofit didn’t fail the way my other companies had, and here’s why. Promoting from within to assure continuity while embracing a new perspective helped the company survive, and thrive. For longtime supporters and colleagues, this sort of leadership transition can be scary. But I promise it’s better than the alternative. At a certain point, you have to step aside to preserve the legacy you’ve built; failure to do so imperils the entire enterprise. Yet according to a 2016 report from Concord Leadership Group,  77 percent of nonprofits surveyed lack a leadership transition plan.

For a country that claims to cherish independence, most of our nonprofit organizations remain oddly attached to their founders and longtime leaders. Conversely, our former rulers in Britain have embraced the notion that change is necessary for forward movement. Since 1992, the Donmar Warehouse has had four artistic directors. The Public Theater has had four artistic directors as well—in 65 years. London’s Young Vic has had only two artistic directors—the same number as Roundabout Theatre Company. The difference? The Young Vic was founded in 2000, while Roundabout has been around since 1965. Britain’s new-play touring company Paines Plough has had 11 artistic directors since 1974. In that same period, Manhattan Theatre Club has had one.

I asked British director Josie Rourke why this might be. By age 35, Josie had already served as artistic director of both the Bush Theatre and the Donmar Warehouse, and she pointed out that in England, these positions are viewed as a public service, albeit a coveted one. They are paid far less than their American counterparts, so they are not incentivized to stay put. In addition, artistic directors are expected to depart their organizations not only to clear a path for new leadership, but to form new companies as well. Their culture depends on these artistic leaders to continue to produce, in other organizations or as commercial enterprises. (There’s also a duty to create more work for trusted collaborators, as the new ADs usher in their own teams.) 

I mentioned that I work in real estate. When a listing is advertised with the line, “First time on market after 40 years of family ownership,” it almost always includes the phrase, “Bring your contractor and architect!” The work of restructuring an outmoded organization is not as physical as renovating a building, but the perils of deferred maintenance are just as dangerous. You can’t allow your house to fall into disrepair. You must keep up with changing codes, modern tastes, new ways of addressing sustainability.

I propose that leadership transition in the American theatre should mean leaving the institution in “move-in condition”. We handed over the 24 Hour Plays as a healthy company ready for its new team to inhabit, not as an estate sale in need of gutting.

If we learn to recognize and nurture talent from within our organizations, we can build a sustainable model for succession that preserves the ethos of our companies without slipping into outmoded forms of leadership and artmaking. Those of us who have been lucky enough to lead can move on to new, exciting projects while supporting and mentoring the folks who take over. We may not need term limits per se, but a smart succession plan can be liberating. As George Washington sings in Hamilton, “We’re going to teach them how to say goodbye.” 

I’m still on the board of the 24 Hour Plays and I remain in ongoing contact with Mark and the team there, pitching in when I’m useful, participating in the radiant warmth of the community, and, yes, contributing financially to their success. I enjoy a deeply satisfying and healthy relationship with the project that once felt welded to my identity. Who was I, if not Tina24hour? I am grateful that I have had the chance to find out.

I hope others will join me.