Letters from the Homestead: February 2024 💕
"State of the Freelancer" reflections and thoughts on returning to teaching...
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.
State of the Freelancer
It’s been about three and a half years since I transitioned to full-time freelancing, cutting the cord from my full-time job in August 2020. There’s nothing terribly unique about a millennial leaving the traditional workforce in “season one” of the pandemic. I wasn’t the only one, and I’m grateful for that silent camaraderie. (What a time to be alive.)
But I hit a milestone this month as a freelancer. I was finally able to release the last of the ongoing contract gigs I only did for the money. When I first began freelancing, I added on multiple small income sources just to see what was possible for me in the market. This meant I did all kinds of things: academic editing, romance novel writing (pretty proud of that one), audiobook narration and voiceover jobs, content development for online courses, and grading. Grading for online courses was one of the last things I held onto as my other income sources (writing, grants/fellowships, and teaching) increased.
And this month, I finally let it go.
It was a corporate-type position, one where I was a remote worker who hardly ever interacted with other employees. I graded assignments from teachers doing their professional development credits and didn’t hear much from anyone unless I did something wrong. It was very easy. It was also very boring.
As soon as I took it off my plate, I felt time open up in front of me. I felt less anxious (this job didn’t take much time, but its to-do list was always following me). And I also had the headspace for finish my second novel manuscript and send it to my agent. (!)
[ Tangential reflection on being a freelance writer: Writing takes a lot of up-front investment. For example, in order to take the step of getting a literary agent (and hopefully seeing your book get a deal!), you have to give a huge investment of unpaid labor for just writing a book. For me, switching to freelancing gave me more of the creative headspace I needed to do this labor. I don’t think I could’ve started writing novels if I were still working as a professor. Teaching at a university and doing academic research takes so much creative energy. ]
All around, this small release of a gig I no longer needed made a difference for me. I wanted to log it here for the milestone that it is.
My biggest takeaways in 3+ years of freelancing:
No online gig work is entirely dependable, especially in a creative field. The market is always changing; your contacts/leads leave their positions and you start over; skill sets are rapidly evolving; and the companies hiring you would love to pay you less.
In creative fields, the best ongoing freelance opportunities come from in-person connections (that may or may not be sustained online). Some of my most dependable opportunities in my workload come from creative contacts in my city, not from people I’ve never met in-person. (Obviously, this is super different from freelancers working in STEM. So it goes!)
If you get one grant, then your chances of getting more grants increases. I’m learning that grant funding in the creative arts is like building a resume for potential investors.
The beginning stages of a freelance workload (years 1-2+) are chaotic. You say yes to everything. You spend lots of unpaid hours figuring out new skills. You work good paying jobs that don’t really align with your interests. But you have to go through this season in order to figure out what’s really sustainable for you.
Anyway, hooray for taking control of how we spend our time! I know I write about freelancing a lot in this newsletter; I hope I don’t sound like a broken record. Just hoping to share/process some of what I’ve been learning these past few years.
Thoughts on getting back to teaching after saying goodbye to the university…
When I zoomed with my academic dean in 2020 to tell her I was resigning at the end of the school year, she said something very wise: “I don’t think teaching is done with you yet, Courtney.”
At the time, I was like whatever. I was so ready to be done. Working at the university was crushing me—I was anxious all the time, I couldn’t be honest about my identity at my workplace, and I was pouring myself into giving all I could to students while my personal life was falling apart. In an inner sense, I knew that teaching was meaningful to me, but the drama of life and school politics made it so difficult to focus on that good work.
It’s funny—I never could have honestly published a newsletter like this while working at that university. My driving force as a literature and writing teacher was to show students how writing can be an extension of the self and a gift for living authentically. And I couldn’t even do that myself.
My dean was right. Teaching came back to me. It took some time (and some encouragement from friends), but I’ve found myself back in the classroom again. The difference is that now my students are justice-impacted or still incarcerated. And I don’t think of them as students, either—they are colleagues, fellow artists.
I’ve been really struck lately by how the teaching environment that proves healthiest for me is one where authority is flattened in an overtly authoritarian context.
I used to think of teaching as a vocation. In a way, I still do. But I think true vocation is often connected to a sense of context. The ecosystem in which we teach is part of the calling.
In writing about this, I don’t want to sound like I’m trying to over-philosophize about the work of teaching—creative writing is a craft, and I’m committed to teaching it as a craft, not exclusively as a vehicle for life change or healing (though it can do both of those things). I just… well, I’m grateful to be teaching in a context that means something to me. That’s all.
What I’m reading this month…
We are the Luckiest: the Surprising Magic of a Sober Life by Laura McKowen. This is one of the first books I read on sobriety when I got sober in May 2022. I listened to the audiobook (read by the author), and the storytelling made me feel a rush of empathy for my own early months of quitting alcohol for good. Highly recommend if you’re even the tiniest bit concerned about your relationship with alcohol. (The daily question that keeps me sober: “How free do I want to be?”)
Lit: A Memoir by Mary Karr. An amazing memoir by another wonderful storyteller. I read this book for the first time in graduate school. I picked it up again this month to remember how much I loved it—it’s another great read if you’re curious about sobriety.
Spiritual Classics, edited by Richard J. Foster and Emilie Griffin. This is a great collection of writings surrounded around spiritual disciplines (curated by a Quaker editor, so they are mostly Christian writers). I’ve been dipping into this as part of Lent.
The Courage to Teach: Exploring the Inner Landscape of a Teacher’s Life by Parker J. Palmer. Since I’m slowly inching back toward making teaching a larger part of my life, I picked up this book we were required to read in grad school. This book once changed my entire orientation to the work of teaching (for the better); I’m re-reading it now to remember what drew me to teaching in the first place.
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 February.
Teaching artist work for Prison Performing Arts. Teaching a weekly writing workshop and teaching Spoken Word regularly in a men’s prison. This month, I also continued leading some writing sessions at a probation/parole center.
Playing piano for a local Catholic middle school’s chapel service. I’m learning to play a lot of gospel tunes and Mass music. I’m a pretty mediocre piano player, but this is one of the highlights of my week. (This gig is totally unrelated to my work as a writer, but I enjoy it so much that I’d probably do it for free. Middle school girls are fascinating, y’all.)
Paid Substack subscriptions. Thank you to all of my paid subscribers. It means the world to me that you make a financial contribution to my work.
First blush of spring 🌸
Midge the cat bids you a happy False Spring from the Midwest. May the confusing weather remind you that all is chaos.
Also, I want you to know, reader, that I send out this newsletter with lots of bits about my life, but this doesn’t mean I’m not carefully watching what’s happening in the world right now. I’m doing my best to be a witness—not look away from the news, not become immune to tragedy.
Yours,
Courtney, Mistress of the Homestead, and Noble Midge
Never a broken record. Always a beautiful reflecting pool 💜