Letters from the Homestead: May 2023 ⛅️
A month of feeling like a real playwright (and the slog of "early summer malaise")
Emily Dickinson called her Amherst home “The Homestead.” I lovingly call my apartment in St. Louis the same thing (although I definitely get out more than Dickinson). This monthly newsletter is my attempt to work through what it feels like to put down roots as a writer in my own Homestead.
Feeling like a working playwright.
One of the first things people ask when you tell them you are a playwright is, “Oh, that’s cool. Do you have anything playing now?”
95% of the time, the answer is no.
This month, I lived in that dreamy, intoxicating 5%. I got to say yes and yes and yes. “Why yes, I do have something that just finished! And, yes, another thing is opening soon! Yes, another play reading is coming up, too!”
This is so rare. It just, like, does not happen. I’m doing my best to enjoy this busy time, but I’m realizing that you don’t really perceive that you are a working playwright until you are just working as a playwright. What excites me the most is that I’m a working playwright who didn’t do the normal things that working playwrights do: I don’t have an MFA, I didn’t move to New York or Chicago, and I don’t have lots of “preciousness” about the plays I’m writing. I write plays that I like writing and I’m working with people who are kind and good.
Why don’t we talk about this more as an option for playwrights?
Why don’t we encourage playwrights to lean into where they are planted, instead of encouraging them to move to the cities with the most recognizable names?
Would we have more original plays in lesser known cities if we encouraged playwrights to just… stay?

When I lived in Waco, Texas—a college town—a friend of mine used to describe himself as a “stayer” in a town full of “leavers.” This past month of busyness as a playwright has reminded me of the value of being a stayer. In St. Louis, I’m a proud stayer. And this month has filled my heart with St. Louis love.

I’m wondering, though…
How does a working playwright sustain this?
Will there come a point where people in St. Louis are tired of Courtney Bailey plays? Will I get in a rut with my structures and stories? Will I get stale? Will the desire of organizations to spread the love to younger writers (as they should!) discourage me as I’m still looking to innovate (and also endlessly viewing myself as “emerging”)? How bad do I need an agent for playwriting? Is there any viability of my work outside of St. Louis and my own artistic community? Are my plays getting repetitive? Am I actually telling the same story over and over and over again? How hard should I try to push into other mediums?
These are the things I’m thinking about these days. Is the only answer to lean into a “company model”? Or do I stay on my own? Or a mixture of both?
I’m not sure. I’m grateful for a strong spring of being a working playwright, but I’m afraid to get my hopes up just yet.
There’s too much work to be done, to be made, to be enjoyed.
Ah, yes, the “early summer malaise”
It’s basically depression, but the early summer malaise has hit me hard this year. The Summer Solstice is still weeks away, but the post- Memorial Day heat has arrived in St. Louis. The heat clogs up my mind. My AC runs so loudly that my thoughts are mixed with static. I’ve switched to pajama shorts. I hate shorts.
One strategy that’s helped me the most with my own depression is to think of her as a ghost (much like the one I was sure haunted my apartment last fall). I’m not afraid of ghosts, not really, so viewing my depression as a haunting means that my orientation to her is one of curiosity. When I am depressed, I try to get curious about the ghost. What thinned the veil and brought her to me? Is there unfinished business? Did I step over the grave of something yet-to-be healed?
I’ve struggled to handle the haunting well this month. There’ve been plenty of naps, some unnecessary retail therapy, and lots of staring at the ceiling while listing to an audiobook on “healing.”
Unlike other depression hauntings, I know the exact origin of this one.
It came on the first of the month: a notification that my pandemic novel manuscript, which has weathered the querying trenches for over two years, is in the final running for publication with an amazing independent press. It’s not a publication offer, but it’s a “strong consideration.” This is, like, a super amazing pretty fancy what a shock that they even read my manuscript independent press. And I am feeling the anxiety and stress of this close-call, in large part because I had shelved this manuscript to focus on another.
This book was supposed to be shelved. I tucked it away in a poorly labeled folder in my computer, only to be recovered after the next one was drafted. I wasn’t supposed to worry about whether it would have any more “close calls.”
But here we are again. Another “close call.” One of the closest calls yet.
And my mind seems to be shutting down with the nervous waiting. It’s amazing how a near-breakthrough can make you freeze up with something like despair, in part because consistent rejection has taught you to prepare for a “no.” It’s even made me get my religion back, praying to saints and angels that maybe, hopefully, please please please this time will be a “yes.”
If you are the praying sort or you want to light a candle for me and this book, I’d be very grateful. 🕯
📆 For your theatre calendar: new plays I hope you’ll come see if you are in St. Louis!
If you are local to St. Louis, I sincerely hope you will come out and see these new works for the stage. The first is a one-night-only staged reading, and the other is a brand new collaborative play that I’m extremely proud of: a Brechtian adaptation of The Breakfast Club which we have cleverly titled The Brechtfast Club.
Here are the details for both:
The first is the public reading of Margaret Fuller Magick Show, a new playscript of mine funded by the Regional Arts Commission of St. Louis.
WHEN: Monday, June 5th @ 7 pm
WHERE: St. Louis Shakespeare Festival's rehearsal hall (3333 Washington Ave, STL)
WHAT: Margaret Fuller Magick Show is a brand new play about a nineteenth-century American feminist trying to cheat death on a magickal cruise ship that is definitely sinking at the end of the night. A comedy! Less than 2 hours!
COST? Absolutely free. Please feel free to just show up. There will be complimentary wine/beer/soda.
The next is the premiere of ERA's newest collaborative work, The Brechtfast Club, co-written by Lucy Cashion and myself. Opening this Thursday!
WHEN: June 1-10, Thursdays through Saturdays @ 8 pm
WHERE: The Chapel (6238 Alexander Drive, STL)
WHAT: The Brechtfast Club is a Brechtian adaptation of John Hughes' cult classic The Breakfast Club. Our version is set in East Germany before the fall of the Berlin Wall, and each member of our "Brechtfast Club" is a Stasi operative. This is a weird, dark, and experimental game we've built for ourselves, and we hope you'll visit us in East Germany. 90 minutes!
TICKETS: Very limited seating. You can find tickets here.
What I’m reading this month…
My reading life has been all over the place this month, but these are two books I’ve settled down with. There are also lots of audiobooks I could include on this list, but the truth is that I jump around from audiobook to audiobook so frequently that I can’t keep good track of them. Hoping to get better at cataloging this.
You Could Make This Place Beautiful: A Memoir by Maggie Smith. This is a new memoir by a poet I love. It’s something of a “divorce memoir,” but it’s written through the eyes of working writer. Really wonderful.
The Unabridged Journals of Sylvia Plath. These journals are fascinating, chaotic, and vibrating with Plath’s unconscious prosody. I love it. I’ve been dipping into this collection whenever I’m hunting for new sentences, new ways of saying things. She writes in chaos-mode and it’s delightful.
How I made money this month $$$
I believe freelance artists should be more upfront about how they support themselves financially, rather than maintaining the illusion that they are fully supported by their art (they usually aren’t). This is me attempting to live out that principle. So, here are all the ways I brought in money to the Homestead for the month of May.
Performing in a PPA play with Northeast Correction Center artists. This was a fun culmination to the writing process of The Caverns of Wingwood. Not only did I get to write the play alongside the artists, I also got to perform it with them.
Writing workshop through PPA. Leading a weekly writing workshop for PPA Alumni and other local artists/writers.
Helping middle school girls write an “opera” through Opera Theatre St. Louis. Finished this gig this month. I am not built for teaching the youths! They wore me out!
Facilitating online graduate literature classes. Still grading about five essays on Jane Eyre each week. 😂
Catsitting! My parents are on a two-month road trip with their camper, so I am hosting their two very elderly cats for June and July. Thanks, mom and dad! 🐈 🐈
Paid substack subscriptions! Thank you to my paid subscribers for supporting my work!
Be safe from the summer hauntings, my friends.
I hope you’re staying cool in the early summer heat. I’m trying to get my bearings with the season change, making big bowls of pasta salad and sleeping in shorts. I try to remember wintertime, when the cold was so bad I dreamed of June.
Tonight starts a new month.
Yours ever & etc., etc., etc.,
Courtney, Mistress of the Homestead, and Noble Midge the Cat 🐈⬛