I recently wrote the most brazen cover letter of my life. This was for the top job at a nonprofit I know well – a job that I had already told myself I didn’t want. But then came a gchat from a dear friend that was basically “you applied for this, right? I just told the recruiter to hire you,” and over the course of telling him why I had not in fact applied for the job I whipped myself into a frenzy about what I would love to do if I were given the reigns. “See? This is why you should apply,” he said. And so, I did. And I was honest.
The many systems of oppression baked into the foundation of this country and our city are also alive and well in our arts and culture organizations. And now, the American theater has come to a crossroads. As we continue to emerge from two and a half grueling pandemic years, the dual forces of nostalgia and a scarcity mindset are encouraging us to scurry “back to normal” as quickly and cheaply as we can. But we are not the same people we were in February 2020. We have an opportunity to recognize that “normal” wasn’t working for everyone, which means it wasn’t working full stop.
I believe the [organization] can lead by example and take the combined opportunities of the broader cultural context and its own leadership transition to ask the deep, existential questions that so many in our field are afraid to ask.
If given the opportunity to serve as the [organization’s] next [HBIsugarcoatC], I would, with care and rigor, take this organization down to the studs.
I believe that, in order to be able to deeply listen to and integrate the community’s feedback, the next [leader] as well as the Board of Directors must be able to stomach the possibility that the answer [to whether the org is serving its community] is “no” or at least “not like this.” I am not advocating in advance for the dissolution of the organization I’m applying to lead – but I want to be clear that without creating room to openly ask deeply existential questions about an organization’s efficacy within its community, continued relevance, let alone new growth, is never possible.
I had a lovely first interview with the firm leading the search. The recruiter asked me for my availability for the next round. And then – the selection committee did not invite me to move forward. But what I got from the experience of telling the full, unvarnished truth in this process is proving to be far more valuable.
Having been socialized as female in the capitalist hellscape of the late 80s/early 90s, I was taught that the path to success was paved with saying no to drugs and “following my bliss.” I was assured that I could grow up to be anything I wanted to be if I worked hard, was a good girl, didn’t cause trouble, and waited my turn.
Fast forward 30 years, and this conditioning, like a polka-dotted Mary Engelbreit nightmare, bloomed where it was planted, and here I am, spending a great deal of time, effort, and therapy working to weed a whole seed catalog’s worth of perfectionistic, people-pleasing invasive species out of my brain garden. Figuring out what I actually want, what “bliss” or at least contentment looks like, how to essentialize my values and let alignment with them measure my success (rather than counting the pages in my sticker-book of “attagirls,” admiring the artifacts of a job well done begrudgingly affixed to it by the powers that be): this might be, as it turns out, my most challenging life’s work.
For perhaps the first time, while I wrote this cover letter and answered first interview questions, I didn’t sugar coat my ideas or try to bend my responses into what I thought would please the search committee. I owned my experience, my point of view, and my understanding of the moment in which we find ourselves and the work I believe is required to anchor our efforts in authentic equity and justice. Turns out, I might no longer be content to be a good girl, to not cause trouble, to place other people’s approval over my own integrity and vision.
When I was younger, I remember hearing that the difference between a woman under 30 and a woman over 40 was this: a woman under 30 walks into a room thinking “oh god, I hope they like me” while a woman over 40 walks into a room thinking “oh god, I hope I like them.” This is, as is any such distillation, an oversimplification. But here’s what: I remember hearing that in my 20’s and thinking “oh god, I hope it’s true.”
Well, Past Jessie, I’m happy to report that, at least when it comes to how you make the money that lets you live inside the house, it just might be.