What Substack Taught Me About Nimbleness, Improvisation, and the Absolute Necessity of Mistakes

Part II of II

By Jeannine Ouellette

I’ve built a writing and teaching practice, and, indeed, an entire life, on the power of nimbleness, improvisation, and the power of embracing mistakes. Naturally, I gravitate to others who espouse this philosophy, like improvisational violinist and computer artist Stephen Nachmanovitch, who explores these concepts in his classic Free Play: Improvisation in Life and Art:

The literature on creativity is full of tales of breakthrough experiences. These moments come when you let go of some impediment or fear, and boom — in whooshes the muse. You feel clarity, power, freedom, as something unforeseeable jumps out of you. The literature of Zen… abounds with accounts of kensho and satori — moments of illumination and moments of total change of heart. There come points in your life when you simply kick the door open. But there is no ultimate breakthrough; what we find in the development of a creative life is an open-ended series of provisional breakthroughs. In this journey there is no endpoint, because it is the journey into the soul.

This philosophy aligns perfectly with my own beliefs about creativity, and applying those beliefs to my entire creative life, including the auxiliary work of writing (teaching, newsletters, book events, etc.), consistently pays off because it permits me to take chances and be less afraid of failing. After all, creativity demands failure. Only through failure do we ultimately discover newness, and newness lies at the heart center of all creative work. Never failing means doing only what we already know how to do well, which, by definition, is not creative.

Perhaps due to my hardscrabble biography (early childhood sexual abuse, transience, familial isolation, foster care, etc.), my writing and teaching have always been grounded in the mystery and magic of uncertainty. I have long asked myself and my students to “peer over the edge of doubt,” where new things come from. And in 2012, I founded my creative writing program, Elephant Rock, on the power of “negative capability,” a term coined by the Romantic poet John Keats. In a letter to his brothers in 1817, Keats described negative capability as “being in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.” He also said befriending uncertainty was essential for artists.

I agree.

My Substack newsletter, Writing in the Dark is only the most recent manifestation of my devotion to this philosophy. The newsletter emerged from a popular workshop by the same name, which I founded in March 2020, right after signing a publishing contract for The Part That Burns, the debut memoir I’d spent my whole life writing. Not only was I heartbroken over the pandemic timing of my book deal, I was also earning my living as a teacher and leader of group workshops and retreats—in person.

What would I do now?

The only thing I could think of was to create an online space for people like me: people who were afraid, losing their livelihoods, staring into the abyss and flailing in their creativity, but determined to somehow create anyway, on however small a scale, even as the world burned. I called that workshop Writing in the Dark, and offered it on a sliding fee scale down to zero (based on an honor system with no questions asked), so that it would be accessible to anyone with a computer or phone. I intentionally structured a low-pressure but high-rigor space, where we could be serious about art but gentle with ourselves and each other. The first session kicked off in April 2020, and it flourished beyond my wildest imagination. Writing in the Dark is a generative workshop (emphasis on creating) and essays and stories begun in the workshop have gone on to be published in many of my favorite journals, including, Fourth Genre, Hippcampus, Sweet Lit, Entropy, Manifest Station, and, yes, Brevity.

From that one swift act of nimbleness and improvisation—an act that I absolutely recognized might not work, especially with the sliding fee scale down to zero—grew a beautiful and mighty creative community of several hundred writers making work despite the chaos around us. And while the workshop does foster community in ways I never foresaw, it also provides a respectable income for me (writers truly live up to the fine print of the honor system, which asks that those who can afford to pay full do so, and that everyone else pay as much as they can without hardship; only a few writers have ever needed to pay less than half).

I didn’t realize when I started Writing in the Dark that, one year later, my students would rally to make the launch of The Part That Burns a great and celebratory success, even in the midst of an ongoing strict lockdown. Community, it turns out, is everything.

Everything!

As my mentor, the poet and teacher Paul Matthews, says in his exceedingly strange and unusually religious craft book that I dearly adore despite being not at all religious myself, Sing Me The Creation: A Creative Writing Sourcebook:

Maybe when we meet there seems to be nothing at all between us; yet if you give me your word I can reply with the next, collaborative, responding to questions asked, needs recognized, testing each other’s immediate joys and fears in the writing. That is how I started my work as a poet-teacher—with nothing, almost, with simple acts of human language—till gradually I became aware that through a word or a sentence shared in writing we could move into the presence of a communion greater than anything I had intended. At such moments it was no longer a classroom with me, as teacher, at the center. It became a “circle of truth, poetry, and love” in which we were all servants of the Word … that is beyond any skill or genius that we might have in language.

Ultimately, Writing in the Dark (both the newsletter and the workshop) reflects Paul’s words. And while both endeavors do contribute substantially to my livelihood as a writer, I continue to keep my focus on community over commercializing. This way, I can still be nimble, improvise, and make mistakes rather than feel pressured to perfect these offerings for maximum market appeal. When I care too much about the outer aspects of that perfection, I freeze, and when I freeze, I create nothing. I’ve been best served by resigning myself to mistakes while assuring myself I can continue to refine, revise, and improve my offerings going forward—which, indeed, is easier to do in the company of many enthusiastic and invested readers, writers, and students as active participants and collaborators and—increasingly as the community deepens—true friends.

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Jeannine Ouellette’s memoir, The Part That Burns, was a 2021 Kirkus Best 100 Indie Book and finalist for the Next Generation Indie Book Award. Her work appears widely in literary journals including Narrative, Masters Review, NAR, Calyx, and other journals, as well as on her Substack, Writing in the Dark. She teaches through the University of Minnesota, Minnesota Prison Writing Workshop, and Elephant Rock. Find her at jeannineouellette.com.