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

Part I of II

By Jeannine Ouellette

I recently launched a Substack newsletter, Writing in the Dark, based on the premise that writing is a metaphor for life. The idea is, everything we do is related to writing because writers today must, first and foremost, keep language capable of telling the truth and continue creating even (or especially) through uncertain times.

Writing in the Dark became a Substack bestseller within weeks of launching—attracting attention from Electric Literature, Literary Hub, The Write Minded podcast, The Writer’s Bridge, and even the Brevity Blog—even though I’m decidedly not famous and have a relatively small platform. What it took to build something quickly from the ground up was leaning into nimbleness, improvisation, and the willingness to make, accept, and even celebrate mistakes. These are all qualities I consider essential for creative persistence, renewal, and success (however you define that).

I launched Writing in the Dark in November 2022, and last month I crested 2200 total subscribers, about 400 of them paying, with both numbers rising steadily. This has been fascinating (and exciting!) for me because, again, not famous. I have one literary book with a micro press and fewer than 5K unique followers on all my socials combined. I’ve never even posted to TikTok (sadly). The truth is, I only signed up for Substack because I was tired of using Mailchimp as the platform for my thirty Patreon supporters to whom I was already delivering Writing in the Dark in a previous form (a slightly less robust monthly missive on the craft of writing). I did import the 500 or so Mailchimp emails I’d collected over the years through my teaching and my website—but I offered those individuals an overt opt-out from this new longer and higher volume newsletter, knowing they might not even remember who I was, let alone want me cluttering their inboxes. I expected my list to shrink for a while out of the gate.

And this is where nimbleness, improvisation, and embracing mistakes come in. I deliberately did not torment myself over setting the newsletter up. I am wildly unskilled with all things technical. So I hired a former student to spend a few hours setting up my Substack with graphics and headers, and importing some old blog posts from Patreon and my website to give potential readers a sense of my voice before subscribing. Then I tinkered for an hour or two myself before hitting go.

Hitting go meant doing the one thing I know how to do (and most love doing): to speak passionately, earnestly and as generously as possible about creative writing from my 30 years of experience as a writer and teacher. I share concrete specific tools, prompts, readings, and strategies I use with myself and my students to generate and improve essays and stories. In many ways, Writing in the Dark is a more crafted and polished extension of my classroom. And because I love community and seek to build it wherever and however I can, I emphasize interaction in the Substack chat and comments.

If you check out Writing in the Dark (or even if you don’t), you might wonder whether it would be even more successful by now if I had pressured myself more regarding layout, design, artwork, strategy, marketing, etc. Maybe that’s true. But those things are outside my skillset, and I don’t enjoy doing them. As writers, we have to do some things we don’t enjoy, yes. And I have recently made fun updates to the original design with regard to aesthetics and organization of the content (because the content keeps evolving). But had I pressured myself unduly over the more technical aspects of setting up the Substack, instead of just writing from the heart, I might never have launched it at all.

Instead, I lowered the stakes and reminded myself that very few people were looking at it and I could change and improve it slowly as I learned the ropes. I’ve made plenty of mistakes, too, from formatting inconsistencies to typos (gah, the typos) to one glaring error that ended up being my most popular and well-publicized post of all time—it was even boosted right here in the Brevity blog. That mistake was sending what I intended as a free public post on the most important things I’ve learned as a manuscript editor to paid subscribers only, when I’d meant to send it to all subscribers. The only way to correct that was to re-send the post with an apology (double emailing, the horror!). Now, because it’s my most popular post ever, that correction is pinned to the top of the Writing in the Dark homepage, a testament to nimbleness, improvisation, and the power of embracing mistakes.

And that—the depth of creative possibility found in this trinity of nimbleness, improvisation, and mistakes—is what I want to further unpack tomorrow, in part two of this post.

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Join Jeannine’s Substack here

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.