Substack Visionary Jeannine Ouellette: How Generosity and Expansion Lead to Meteoric Substack Growth
Part of the Substack Visionaries Series
Welcome to the Substack Visionaries Series!
The Substack Visionaries Series spotlights those who approach Substack as more than just a newsletter and blogging platform.
Substack visionaries use Substack’s many features and tools to expand their work and lives, redefining traditional career paths and how they support themselves doing what they love.
They pursue Substack growth (financial, personal, artistic, subscriber, etc.) in innovative, unique ways.
Upcoming spotlights include visual artists, spiritual leaders, activists, videographers, chefs, health and wellness guides, and more.
Today!
Substack Visionary of Writing in the Dark: Teaching on Substack
Jeannine Ouellette is a force of nature. To say that her Substack Writing in the Dark has experienced meteoric growth is an understatement. In just seventeen months, she went from zero to 7500 total subscribers and 1332 paid subscribers. Seventeen months. She had very little platform besides her word-of-mouth reputation as a writer and teacher.
I’m celebrating Jeannine’s stats and her ability to tap into the many features and avenues of growth Substack offers and make them her own.
She didn’t just get on Substack, start writing, arbitrarily paywall, and expect to grow her paid and free subscriber base and develop professionally, personally, and artistically.
She took her talents and skills, considered how they’d work best on Substack, thought a lot about her subscribers and what they needed, and developed a thoughtful strategy for growth.
She envisioned how Writing in the Dark could function as more than yet another newsletter.
As she says in this interview, her astronomic growth resulted from thoughtful strategies that were authentic to her. (Then she and I worked together in my 1:1s to amp it up even more.)
Jeannine is an award-winning author and a beloved creative writing teacher. Her memoir The Part That Burns was a Kirkus Best 100 and a finalist for the Next Generation Indie Book Award with starred reviews from Kirkus and Publishers Weekly. Her writing appears widely in literary journals. She teaches at the University of Minnesota, the Minnesota Prison Writing Workshop, and (of course) her Writing in the Dark newsletter and community on Substack.
This interview is gold. Jeannine imparts so much inspiration and so many growth tips. Read on and…
*For those who want to go deeper, you can read the full conversation here.
What is Writing in the Dark?
Writing in the Dark is about paying closer attention to the place where language and the world intersect, and how this helps us become better writers and humans.
What’s made Writing in the Dark go more than any strategy—though I am strategic—comes down to something a reader named Imola said a while back: “Writing is the only home I have ever had.” That hit me. Writing is the only home I’ve ever had, too.
That’s the heart of Writing in the Dark.
Before we go any further, what advice would you give someone who’s struggling on Substack?
My wish would be for everyone not to struggle on Substack. Can I offer a short list of anti-struggle strategies?
Don’t worry too much about posts that don’t get any reaction; you can always resurface them later, after you’ve grown, for archival posts! Some of my early posts from 2023 had almost no reactions, but they weren’t a waste. They’ve done much better when recycled as archival posts.
Don’t watch your unsubscribes. I never, ever look at them, and you probably shouldn’t either. Just keep building your ship and sailing it as best you can.
Make friends with your readers and with other Substack writers. I’m an introvert, so it takes time for me to get to know people and become familiar with their work. It’s okay if you’re like that, too. You’ll find your people!
To the above point, be a good literary citizen—a rising tide lifts all boats.
Be super curious about your topic and keep learning so you can stay excited and have more to share. Otherwise, you’ll get bored and burnt out.
You don’t have to know everything about Substack, all the growth strategies and hacks. I don’t. I still get help from my friends, my kids, and people I pay, like Billie Oh, my part-time assistant (and youngest adult child), and you, Sarah, because you’re absolutely brilliant at Substack. So I get help and expert advice.
Advice aside, you have to trust your gut, too. The way I treat headlines, post length, and paywalls isn’t conventional, but has been working for me. That doesn’t mean it will work for someone else, though! There are best practices, and there’s also the art of it. You have to find your own sweet spot, which requires trusting yourself to do your own thing and see what happens.
Always remember: we’re not doing brain surgery. We’re writing newsletters. Keep the stakes low enough that you don’t get paralyzed and frustrated, which will only smother your creativity and productivity. Stay open and loose and connected to joy. Otherwise, what are we doing?
We have to remember that struggle and work are not the same. I work hard at Writing in the Dark. But I don’t struggle or hustle. I just keep writing about a topic I love—writing–while trying to understand it better and share it with passion. I know the urgency to get work out there, get it seen, get subscribers, get paid subscribers.
How did you end up creating a Substack newsletter that included your writing and teaching?
I launched my newsletter because I had a handful of supporters on Patreon, all former or current students, whose perks included a newsletter with craft essays, writing exercises, inside looks at my work-in-progress, etc. I was sending that on Mailchimp, but I was really bad at Mailchimp. I’m technologically challenged.
So I hired one of my young students to help me move to Substack. After that, the whole world opened up!
Writing in the Dark is such a value. You’re basically giving people an MFA in creative writing for practically nothing. How do you determine what to offer free and paid subscribers?
Thank you so much! That’s amazing to hear from you!
Our approach to paid and free content is super specific. My free/paid strategy is an extension of my overall ethic—I choose to be generous and expansive, while also respecting myself and the value of my work and expertise, and equally respecting the people who support my work.
Most posts are paywalled, but the previews are really meaty. They’re not teasers. There’s a ton of valuable content in those long previews, and people tell me that all the time. Sometimes they even apologize, like, “Sorry I’m still a free subscriber, but I’m getting so much value out of the free content.” And I’m like, “Don’t be sorry! That’s the point!” If what I’m creating resonates with free subscribers long enough, they might upgrade to participate more fully, because writing exercises are usually paywalled, and comments always are.
Paywalling the comments keeps our space safe and troll-free. Plus, I teach and interact in the comments, so those who want direct access need to upgrade. Many do. Writing in the Dark has a high conversion from free to paid, around 18%.
How do you create a sense of a classroom or workshop on Substack?
It’s easier than I thought it would be!
The comments are huge for creating community.
Our full-access founding level also helps to create a classroom feel with audio and video and live salons on Zoom, open mics, silent write-ins, yoga nidra meditations, group celebrations after seasonal intensives. That stuff builds camaraderie.
But the intensives themselves are probably the biggest driver. My intensives are special and really create a group spirit, a sense of people doing something significant together. People get to know each other extremely well during intensives—they’re called intensives for a reason!
People are always saying how good it feels in the Writing in the Dark community. I’m passionate about rigorous and safe creative spaces. My abusive childhood heightened my sensitivity to and compassion for the human condition. I see how people’s work opens up and gets more interesting and original, too, as they feel more willing to take risks. I taught elementary and middle school for ten years before teaching adults, and the lessons I learned teaching kids underscore my approach. Kids can’t learn if they don’t feel safe … and adults can’t, either.
Rigor and kindness are not mutually exclusive. I care about how things feel.
Your subscribers gladly pay to have access to you and the community you’ve built. I always say that people don’t understand when we paywall words—those words are free but those words aren’t. They do understand paying for access.
They do! Yes! Participation is probably the greatest value at Writing in the Dark though I always reassure people, because most writers are introverts, that it’s 100% fine to just read posts and work the exercises.
The comments are a goldmine, and that’s where I am every day, hanging out and interacting and teaching. That’s the access you’re talking about, and it’s pretty incredible because of how people show up for each other.
The comments are where that MFA-quality interaction happens–better than some MFAs, really, because of how healthy it is. People are genuinely transforming their writing.
What recent changes have you made to Writing in the Dark?
So many changes. All the changes!
Thursday Threads are new (thank you for that, Sarah!), and becoming a meaningful space for subscribers to engage with each other in a casual, easy way.
Last fall we launched bonus audio and video content and live salons on Zoom for full-access founding members thanks to your great advice. Some people really love that level of connection, being able to see and hear me and each other for a nominal additional fee annually. We know not everyone wants audio/video content, so we still offer the regular annual subscription at a slightly lower cost. Speaking of which, we’ve already changed our pricing structure twice since launching, because it’s a learning curve to find the greatest synergy where our production labor, seeming value of the offerings, and member interest and engagement best align. We’re always paying attention and ready to adapt, grow, morph, etc.
We recently made a tool, a Curriculum Index, to help subscribers find what they’re looking for. It’s a huge deal because our seasonal intensives have all these scaffolded posts meant to be evergreen for all paid members to work at their own pace whenever they want. Pinning the Curriculum Index makes these really valuable resources much more findable.
Writing in the Dark isn’t even two years old, so we’re making constant adjustments and improvements.
How have you given your subscribers a version of the teacher-student or mentor-mentee relationship so many people crave?
I love my subscribers and think about them all the time! I actually know many of them well, too, because I am in the comments every day, interacting with people and learning about their writing and their lives, their joys, fears, goals, and struggles. I read every comment and reply to most, especially on posts with a writing exercise, because I offer thoughts on what I see working best in people’s work.
My approach is to teach rigorously enough for the writers making a serious go of it—publishing books and short work or building their Substacks, even earning a living from words—while also ensuring an accessible, engaging, highly encouraging space for beginners.
Writing in the Dark is truly for anyone who loves language—which is what makes us human. Our tagline is “for people who do language,” which obviously refers to writers … but we all do language. The phrase comes from Toni Morrison’s 1993 acceptance speech for the Nobel Prize in Literature. She said, “Word-work is sublime … because it is generative; it makes meaning that secures our difference, our human difference—how we are like no other life. We die. That may be the meaning of life. But we do language. That may be the measure of our lives.”
I think that’s why Writing in the Dark appeals to such a wide audience–we have a lot of musicians, painters, sculptors, filmmakers, teachers, and also healers, like therapists, doctors, nurses, etc. Lots of people who’ve always wanted to write or used to write and want to again.
Our conversations in Writing in the Dark are intricate and passionate, like a giant literary salon.
How did you adapt your teaching to the digital-newsletter space?
I was all about in-person stuff like writing retreats and workshops with tons of special details, everything full of warmth and intimacy and handwritten cards and hugs and fresh-baked pastries in historic lodges and beach bungalows with turn-down service. That kind of thing. It was wonderful!
Even though I was wary of digital teaching—would my intimate style translate?—I was an early adopter. My first Zoom classes—before most people even knew how to use Zoom—had these super long conversations on Gmail between classes. Students would respond to my class follow-up all week so the thread would grow 100s of messages deep. Eventually, we moved to Mighty Networks to keep our conversations bundled with course materials and Zoom links, etc. In my University of Minnesota classes, I use Canvas, another digital classroom.
So all this prepared me well for teaching on Substack, where I do many of these same things, except instead of Gmail or Mighty Networks or Canvas, it’s Substack posts and comments, plus other dynamic bonuses like audio, video, and Zoom.
I still love in-person stuff and am offering some of that again. The thing about teaching writing in a newsletter format is that most writers learn well through the written word, which helps the posts and comments feel very alive! It’s not static or flat at all.
What was a turning point in your Substack?
I reached out to you, Sarah, last September, to help me better understand Substack and tailor my efforts more specifically to this platform, which has been enormously helpful! From there it’s just been going and going and going.
What advice would you give someone who wants to teach on Substack?
First, make sure you really love teaching, or, if you haven’t taught before, make sure you love people! Having expertise does not automatically prepare someone for teaching.
People need a clear teaching strategy–how they’ll present new material, how/when they’ll interact with students, if/when students will gather in real-time, etc.
So for those who want to teach on Substack, I’d say identify your topic and scope, then maybe narrow it even more, so you can go deep and get really granular. Have some idea of how you’ll share information and interact with your community to give them usable tools and build relationships. But know you’ll inevitably make lots of changes once you see how things actually work in real-time.
Assuming someone does want to teach, they need a niche. I teach creative writing, not the business side of writing, like how to get an agent, where to submit work, querying, pitching, etc. Of course I engage in those activities because I’m a working writer who publishes in traditional venues, including books. But I am not super excited about teaching that stuff, and there are other writing teachers doing a far better job than I could in that space, like Jane Friedman,
, , to name a few.
There are easier things to do than teach, so it only makes sense if you really do love people. Teaching is people-work. If you love people, it’s rewarding beyond belief.
*For those who want to go deeper, you can read the full conversation here.
Housekeeping:
Headline heroes! Thank you for the inspiration for the title of this post and series. If you’re a member of Substack Writers at Work and aren’t using the chat to create headlines that draw in readers, they’re the best:
I've always thought that I have underutilized "Writing in the Dark" and this interview has encouraged me to be more intentional about reading Jeannine's posts. I'm also intrigued by the salon zooms, which i will check out.
By the way, what kind of pastries?
Found this a really encouraging read. I love seeing others (and learning how they) zone in on their real niche!