Substack Visionary Jeannine Ouellette: How Generosity and Expansion Lead to Meteoric Substack Growth

Archived from the Substack Visionaries Series by Sarah Fay | Writers at Work

Until Sarah Fay interviewed me for her series, no one had ever called me visionary (!!), and I’m still stunned and grateful.

In this interview, Sarah asked me about:

• How I adapted from in-person teaching to Zoom to Substack

• Strategies I use to create a “classroom feel” with Writing in the Dark

• Why I prioritize safe spaces above all

• Why you don’t have to be a writer or want to be one to benefit (greatly) from the study of creative writing

• Key turning points in the growth of Writing in the Dark

• Advice for others who want to teach on Substack

Before we dive in, another GIANT thank you to Sarah, who is a truly extraordinary guide and champion for writers here. For anyone wanting to grow their work on Substack, Sarah’s got you.

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.

Writing in the Dark’s Jeannine Ouellette

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.¹ 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.

This interview is gold. Jeannine imparts so much inspiration and so many growth tips.

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.

Thirteen years ago, when I started teaching creative writing, I found I loved helping others discover their writing home, or find their way back inside it after getting locked out.

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. I’ve known this since childhood. 

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?

Actually, my wish would be for everyone not to struggle on Substack. 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. But struggling makes it harder. We only need to write with some originality about something we care about and have a unique angle on. That’s how we add real value to the conversation. 

Can I offer a short list of anti-struggle strategies?

1. 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.

2. 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.

3. 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!

4. To the above point, be a good literary citizen—a rising tide lifts all boats.

5. 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.

6. 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.

7. 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.

8. 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?

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!

How have you adapted your teaching to the digital-newsletter space? 

I didn’t realize I’d be teaching on Substack! I thought I was making a newsletter, not a classroom. But looking back, it’s clear I’d teach here. I’m such a people person.

Early on, though, 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!

And I still love in-person stuff and am offering some of that again, now that we can. But around 2017 I launched some classes on Zoom because I wanted to co-teach with my daughter who lived across the country. So, even though I was wary of digital teaching then–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 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. 

It’s been truly amazing. One member said recently, “You make it seem possible to make stories from tiny things.” I loved that because that’s what writers do, make stories from tiny things–and that’s what teachers do, too, make things seem possible, and it’s so cool to do it on Substack.

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. Our conversations in Writing in the Dark are intricate and passionate, like a giant literary salon. 

One of my mentors, the poet and teacher Paul Matthews, has the most beautiful passage in his craft book, Sing Me the Creation, about teaching, which completely captures how I feel about it:

Maybe when we meet there seems to be nothing 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 human acts of language—until 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….”

Teaching on Substack is a whole other world. 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.

That’s a huge part of my teaching philosophy—how much we can learn from zeroing in on what’s working on the page. The Writing in the Dark method is super rigorous but also deeply respectful of writers as artists.

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. I know whales and dolphins have complicated communication systems, birdsong is a miracle, primates can learn sign language, my dog Frannie knows dozens of English words. But only humans write poetry. Language is the great gift of human existence, and our ability to use it better can change 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. Or who want to feel more alive in their relationship to language and the world, who want to read more and think harder about how words shape our lives as humans, about how plot isn’t just what happens between the beginning and end of a story, but also what happens between birth and death for all of us. 

The common denominator at Writing in the Dark is people who are a little awed by what language can do. Ultimately I write and teach for people who care about making language capable of telling the truth again, who appreciate gut-wrenching writing that does what Kafka says it should, which is be the ax that breaks open the frozen sea inside us, and who want to wield that ax as much as break open beneath it.

I write and teach for people who want to be thrown into the deep and made less comfortable because they believe uncertainty is the key to good art. I write and teach for people who want to look more closely at the world, at the thing itself, even if it hurts (it almost always hurts). For people willing to keep looking until the thing opens like a window to reveal something larger than any of us.

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.” Then she goes on:

Passion is never enough; neither is skill. But try. For our sake and yours forget your name in the street; tell us what the world has been to you in the dark places and in the light. Don’t tell us what to believe, what to fear. Show us belief’s wide skirt and the stitch that unravels fear’s caul. 

I write and teach for people who read that quote and are stunned by it and want to live up to it.

Writing in the Dark is such a value. You’re basically giving people an MFA in creative writing for practically nothing. How did 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. 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%.

Since people might wonder, I did turn on paid subscriptions immediately. My  Patreon supporters had been getting the newsletter as a paid perk, so it felt weird to offer it free on the internet while continuing to receive pledge dollars from the people who’d been generous enough to pay for it already.

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. 

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! 

I’m also passionate about rigorous and safe creative spaces. I taught elementary and middle school for ten years before teaching adults, and the lessons I learned teaching kids underscore my approach. Rigor and kindness are not mutually exclusive. I care about how things feel.

Kids can’t learn if they don’t feel safe … and adults can’t, either. People are always saying how good it feels in the Writing in the Dark community. And I see how people’s work opens up and gets more interesting and original, too, as they feel more willing to take risks. My friend Tyler—he’s a beautiful writer who’s been in recovery for a long time and is also a high-octane entrepreneur and Buddhist monk, an interesting combo—says my superpower is building safe spaces, and he’s not wrong. My abusive childhood heightened my sensitivity to and compassion for the human condition. That’s why I teach in prisons. I get to take this one thing I know how to do really well and bring it where people need it most.

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. Or not work the exercises! There’s plenty of benefit to reading and steeping in the content and letting it work on you. That’s no small thing.

But 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. 

Craft and writing exercises are everywhere. What makes yours different? Because they are very different from most.

My exercises are pretty weird, I know! I use a lot of constraints–don’t get me going on the amazingness of constraints. Plenty of creative theory books talk about it. But the exercises are more than typical constraints, too. They definitely aren’t prompts, and they’re not standard lessons, either. They’re integrated with close readings of published work–close reading is an essential practice I teach in a highly specific way–so the exercises are craft-enriched and often embodied, too. People say my writing exercises fundamentally change the way they think about writing, and, over time, the way they write. The exercises can transform people’s writing permanently for the better.

Because the exercises are so precise, they often elicit work that surprises the writers. That’s what I’m going for—like, let’s try to write something new, something we weren’t expecting, instead of another version of something we’ve written before. It’s so tempting to stay in the safe lane, but the thing is, we already know how to write the way we know how to write. It’s far more exciting to try something we don’t already know, even if it might not work. Experimenting in open mode leads to breakthroughs. That’s where the exercises take us.

Essentially, the exercises build a capacity called “negative capability,” which comes from the Romantic poet John Keats and means being able to dwell in uncertainty and see past what you think you know. A huge amount of writing craft goes into the exercises, all from a slightly askew angle. 

And they’re fun! 

What significant change (or changes) have you made in your Substack (design, content strategy, etc.) in the past three months?

So many changes. All the changes! The newsletter isn’t even two years old, so we’re making constant adjustments and improvements.

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.

And this is probably not design or strategy, but 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.

What was a turning point in your Substack?

Within a month of launching, I published my “Eleven Urgent & Possibly Helpful Things I’ve Learned From Reading Thousands of Manuscripts” post, which went what I then called “a little bit viral.”

I later learned from you, Sarah, in your incredible virality workshop, that my Eleven Things post wasn’t technically viral. But it got a bigger reaction than anything I’d written before on Substack, and things took off. Ironically, I wasn’t trying to write that post for a big reaction. I was geeking out on craft because I’d  just taught a manuscript revision retreat in Mexico, and had spent weeks deep in annotating and discussing manuscript excerpts. I came home hyper-aware of certain patterns and fixable things that can literally make or break a manuscript. 

I  wanted to capture that clarity before it vanished, as clarity does, so I wrote it out for myself as fast as I could. I have a zero-waste writing philosophy, though, so I was immediately asking myself, Hmm, how else can I repurpose this effort? Voila, my Eleven Things post. 

Overnight, Allison K. Williams shared it on Brevity blog, and that’s why within a month of launching, Writing in the Dark had more than 100 paid subscribers. Soon after, Electric Literature included my newsletter as one of seven to improve your writing, and I was invited onto a couple of podcasts to talk about Writing in the Dark—Brooke Warner’s “Write Minded,” and Allison K. Williams’s “Writers Bridge.” 

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 bring their teaching to the platform?

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. 

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, Kate McKean, Courtney Maum, Leigh Stein, to name a few. 

I’m also clear about teaching creative writing, not journalism or whatever else. Yes, studying creative writing will make people better at other genres, but that’s another conversation. I just don’t water down my focus or overpromise or try to appeal to everyone. Being a specialist makes me a better and more exciting teacher. 

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. But maybe even more important is what lies beneath all that: do you love people, love interacting, answering questions, encouraging and reassuring them? Because that’s the heart of teaching. I truly don’t feel impatient when people ask questions about things I already said in my posts. I just keep over-communicating and repeating myself (again, I taught kids for ten years!) and am genuinely thankful because questions mean people care, they’re invested, showing up, wanting to participate.

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. 

Finally, one more time, so this point is kind of first, middle, and last: 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.

1. Of course it’s now been 24 months since WITD was born, and it has grown very considerably since this interview with Sarah, including the addition of our adjacent nine-month SCHOOL program for slow writing.