How "Writing in the Dark" Became a Beacon to Writers
Jeannine Ouellette shares the winning strategy behind her writerly Substack
Hello Bleeders!
It’s been a whirlwind lately—I’ve been grieving, got married, wrote about it for Business Insider, and started my MFA at Antioch University. It's been a bizarre mix of highs and lows.
Amidst all this, I managed to drop a new podcast episode with Chloe Caldwell about publishing and going on submission. Chloe’s iconic lesbian novella Women was re-released by Harper Perennial earlier this month. Did you get your copy yet?
I’m also thrilled to resume our newsletter series with an insightful Q&A featuring
, creator of the beloved craft-centric newsletter . Writing in the Dark is a treasure trove for anyone looking for practical writing tips, philosophical musings on the creative process, and a vibrant, engaged community.In this interview, Jeannine reveals the origins of Writing in the Dark and insights into the newsletter’s success. She also discusses the impact the newsletter has had on her career and generously shares advice on starting and growing your own newsletter. If you're eager to make your writing matter and connect with a like-minded community, this Q&A is a must-read.
Before we dive in, I want to share an exciting opportunity for writers that I’m piloting this summer. Want to bank some serious word count and land your dream bylines while everyone else is on vacation? Join the Midsummer Pitch Party!
For the month of July, we're going to work hard AND play hard. Join my supportive group for daily Zoom sprints, writing prompts, publication targets, and weekly feedback. By the end of July, you'll have written 20K words (!!!) and polished at least two pitches, a flash piece, and an essay, all while boosting your confidence and taking your writing practice to the next level.
⏰ The clock is ticking, and you're running out of time to sign up. Sign up by Sunday night and use code BLEEDERS to save $100. Your writing uplevel awaits!
What’s the basic premise and tagline of your newsletter?
JO: Writing in the Dark’s tagline is “For people who do language.” It comes from a longer Toni Morrison quote from her 1993 Nobel Prize acceptance speech. The premise is, simply put, how to write better. How to make your writing—no matter the genre—come alive, tell searing truths that somehow bridge the divide between the personal and the universal, that bypass cliche and doublespeak and marketese and trends in order to make words matter again. That’s what Writing in the Dark is really about. It’s about, as Wendell Berry says, “making language capable of telling the truth again.” Because that’s what being a writer is really about. All the other stuff—submission, publication, platform, blah, blah, blah—is secondary. The writing needs to matter, otherwise it’s just a pile of words.
When and why did you start your newsletter?
JO: I started it just over a year ago to fulfill a perk I had offered to my Patreon supporters. The idea was to write about writing but also about living in the world in a certain way, an attentive, curious way that can produce art and truth if we can get ourselves to practice John Keats’s theory of Negative Capability, which means befriending uncertainty and seeing past what we think we know. I wanted to see what could happen when we practice all those really hard things in a communal space. It turns out, it makes our writing better, but also makes us better. It makes life more interesting, too.
Who’s your main audience?
JO: People who write, of course—and a lot of them write seriously and at a high level, with multiple published books, etc. But also people who are writing to grow, to better understand themselves and others and the world we share. Writing in the Dark attracts a lot of therapists and healers and activists, for sure, and I’ve noticed a lot of artists, too—painters, weavers, sculptors, musicians, which is really cool. I think writers have a lot to learn from other disciplines, and it makes me really happy that Writing in the Dark is drawing people with diverse artistic backgrounds, as well as just a lot of people who care about being able to look at the world, including our experience in it, and see it as it actually is, and find a way to use language to depict that vividly. To make it seethe and sing.
How is your newsletter differentiated from the other newsletters in your niche?
JO: I think it’s the combination of practical, applicable content—if you are trying to become a better writer, you’re going to find concrete tools, strategies, and devices for improving your writing—and a larger, deeper, vaster conversation about what it means to make art, and, even more than that, what it means to be a human being. For me, talking about “how to write better” without a grounding in that larger philosophical conversation is kind of boring. I want the craft of writing to be as exciting or as devastating, or as eerily soothing as the writing itself. I want Writing in the Dark, even at its most practical, to never forget that the whole point of creative writing is to discover something that fundamentally changes us. Yes, I am interested in the realities and conventions of the marketplace—I publish my work and want it to be read. But if the work itself and the making of the work is not alive, then the publishing end of it means little. One other thing: Writing in the Dark’s community is super engaged and active, and that’s a big part of my vision. The comments are bustling, and people really get to know each other. It’s also totally fine to just read and silently lurk in the comments, but for people looking for a meaningful, creative community, Writing in the Dark offers a beautiful one.
What’s your editorial strategy? Including: What kind of content are you focused on offering? What’s your publishing cadence? How far in advance do you plan your content calendar?
JO: Oh my gosh, I am still flying by the seat of my pants and almost never have very much planned in advance. I am a very disorganized person with top-notch compensatory skills. I publish a minimum of three times a week: Monday is the Lit Salon advice column, which explores every aspect of creative living; Wednesdays are the heart of Writing in the Dark, with the Writing Lab, which includes craft essays and intensive exercises, just lots of content on Wednesdays; and Thursdays we do an open thread. Sometimes I put out personal essays on some of the off days. I also want to start publishing guest essays and interviews, so people should feel free to hit me up if they have something they think is a perfect fit for Writing in the Dark.
How many subscribers do you have?
JO: We just passed the 6,000 mark!
[Editor’s note: This series of interviews was conducted earlier this year. Writing in the Dark now has over 8,000 subscribers.]
Do you offer paid memberships? If so, explain when and why you turned that on, what your subscription offering includes, the cost, how many subscribers are part of your paid community, and any takeaways from going paid.
JO: I turned on paid right away because as I said, the newsletter was originally part of my fulfillment of a perk I promised to Patreon supporters, who were already paying me. So I kind of assumed I should paywall Writing in the Dark. But a lot of content is free. I grew up under the poverty line and have spent most of my life broke, and I am justice and equity-oriented. Meanwhile, I’ve been writing and teaching for 30 years, so at this point, I like to both make a living and make things accessible. Subscriptions cost $7/month or $50/annually and basically include full access to everything I described above, whereas free subscribers don’t have access to the exercises or the comments, and that’s where the action is. Full-access subscriptions are $80/annually and include more “backstage” content like recorded voice memos, video notes, and live Zoom salons, which are really amazing. For our next seasonal intensive, The Visceral Self for embodied writing, we’ll have recorded meditations and candlelight meditations on Zoom. We emphasize community and sticking around at Writing in the Dark, so full-access founding memberships are actually less expensive than subscribing monthly. By the same token, we offer free trials and a lot of free content, so free subscribers tell me they still get a lot of value, and that matters to me, too. I think that’s why our conversions from free to paid are so unusually high at 20 percent. We currently have 1210 paid subscribers.
Have you tried any other methods of monetization?
JO: No.
Tell us about your newsletter’s growth trajectory. What have been the most effective ways for you to promote your newsletter? Did you have any growth spurts, and what did you learn from those?
JO: I wish I knew more about promotion! When I first launched, I’d post on my other socials—Facebook, Insta, and what was then Twitter. Now, I am almost never on X/Twitter anymore, or Insta. I tried the new Threads but couldn’t stick with it long enough to get traction. That leaves Facebook, and I’m not there very much anymore, either. So, I’m not cross-posting much on my socials. But here’s what has worked.
First and foremost, when I have something special to offer, like I’m going to be teaching/talking about a specific element of writing over several weeks, which I call an “intensive” (the next one is The Visceral Self), I announce it in the newsletter in advance and invite people to upgrade to participate. That always leads to growth, and what I’ve learned from that is that this is the kind of content my readers want. Readers love the intensives and talk about them and share posts, which is great.
I also worked with
from and she helped me figure out literally every little detail inside of Substack to optimize what I’m doing and make it work better for readers and for me. The changes I made thanks to Sarah, including our subscription tiers, have helped both in converting and retaining subscribers.Finally, I am very active in the literary community at large, and that definitely helps build the newsletter. I teach writing and present on writing in a lot of different places, from Elephant Rock (my own writing program) to AWP to HippoCamp to the Minnesota Prison Writing Workshop to the Writer’s Center to Hidden Timber, etc., and that helps. And I was lucky out of the gate to get some attention from outside sources like Brevity and Electric Literature and the Write-minded Podcast with
, and later on, had me on his podcast, and I’ve done some other interviews, and I teach a lot, so people have ways to find the newsletter.What’s been your most popular content, and your guess as to why?
JO: My most popular content has been my intensives, where I help people deeply explore a specific aspect of writing (e.g., we’ve done the lyric essay, we’ve done elements of story) over the course of several consecutive posts. I think because it’s incredibly exciting to see your writing transform and improve in a short period of time and to watch that happening for others, too—to share that creative synergy with a cohort of people is just really fun. Otherwise, my absolute top posts were the two I wrote back in December about How I Grew My Substack from Zero to 40K Annual Income in Just 12 Months (Part One) and what I learned from doing that (Part Two).
How has your newsletter served your career as an author? (Aka: Is it a good chunk of your income? Does it help you sell books or workshops? Has it helped you develop material? Has it helped you secure bylines? Etc.)
JO: It is a good chunk of my income, for sure, although I also have a full-time day job as a writer at the University of Minnesota. I have always had a day job to support my writing habit, which gives me peace of mind and allows me to take risks with my writing that I might not otherwise. Beyond the subscription income, which is almost $70K gross now before expenses (I pay two part-time assistants plus other costs), my newsletter has started to lead to some opportunities. Last fall, I was asked to teach in Brooke Warner’s Magic of Memoir series and that was by far the most I’ve ever been paid for an hour of teaching. And recently an editor at the Rumpus solicited an essay from me thanks to my visibility on Substack (still working on that essay). And the newsletter seems to keep sales of my memoir, The Part That Burns, going strong. But I wouldn’t say anyone is beating down my door with opportunities. I wish they would, haha. I do have plans for a craft book based on Writing in the Dark and I am also hopeful my newsletter might give me a little boost when it’s time to query agents with my novel. Fingers crossed.
What’s your #1 tip for writers who want to start a newsletter?
JO: It depends on what you want out of it. Back in my “How I Grew…” posts last December, I was really passionate about telling people they needed to be themselves and have a very clear idea what they were here to say and why they were saying it. Now, I realize that advice was aimed at people who want to make their newsletter into a “thing” of some significance in their lives, you know—like, build a thing with a kind of staying power. And that’s not required. It’s also totally fine to not know, try different things, and just kick around and experiment and figure out in real time what you want to write about and why. But, if you do want to make a thing with staying power, then I think I stand by my hunch that you should feel some real passion for a highly specific topic and be sure to find a way to write about it straight from the center of yourself in a way that no one but you can.
What’s your #1 tip for writers trying to grow their existing newsletter?
JO: Make friends and participate in the community in which your work is centered—not only to spread the word about your newsletter but to continue to refine and deepen your own knowledge. That’s super important. But at the end of the day, the best way to grow your newsletter is going to be to give value and give it generously. If you do this and do it consistently over time, the newsletter will grow, no matter whether you paywall everything or paywall nothing or participate in Notes or not or have an illustrator or not, or whatever. This has proven true again and again. Some of the most successful and lucrative newsletters on Substack are 100 percent free, including
’s . Other highly successful newsletters paywall everything. So it’s not about the paywalls. It’s about content. If the content is exceptional, the newsletter should grow. It might be slow. But it should happen. Sometimes, it doesn’t happen, though, even when the work is really good, and I think that’s important to acknowledge, too. Beautiful work doesn’t always get found and rewarded. It often does, maybe even usually, but not always. And that’s one of the frustrating truths about making a life as a creative person.Shout out another writer-newsletter that you admire and enjoy consuming.
JO: There are so many incredible writers on here it’s almost impossible to narrow this down. But I do want to shout out
’s . I’m late to Esme’s party, but she is so brilliant. I finished The Collected Schizophrenias this winter and am loving her newsletter, which is about, among other things, writing.And a couple of other writers I’ve discovered more recently are
, an ER doc who writes , about living with her husband, who is dying of tongue cancer. Stunning writing that’s beautiful and, yes, sometimes sad, but not depressing—it is about far more than dying, health, or healthcare—it’s about loving and living and creating. One of her recent posts, in fact, was all about the language she and her husband share. Gorgeous, smart writing.I’m also loving
, who writes Unqualified [now ], which is about, among other things, quitting hustle culture (she founded Em & Friends cards and sold it). Emily is one of the smartest writers on here. Both she and Beth Stillman really demonstrate what I mean when I say, write about something you’re really passionate about and can go into intricate depth about, and we’re going to lean in and listen, we’re going to keep reading.Anything else you’d like to add?
JO: Just a word of encouragement to anyone trying to build their own ship and sail it at the same time—hang in there! It’s not easy and sometimes things fall apart, you take on water, all that. But the good news is that there is actually no ship, no ocean. No one will drown. It feels like it sometimes, but ultimately, we’re just writing, putting one word after the next, and if we care enough about both the words and the people who might read them, things will probably work out. They usually do.
Thank you, Jeannine. Break a leg with your novel!
➡️ Subscribe to .
➡️ Follow Jeannine on Twitter/X and Instagram, and visit her website at jeannineouellette.com.
➡️ Check out the Minnesota Prison Writing Workshop.
So… ROLL CALL! 🗣️
Smash that like button and give Jeannine some love in the comments below.
Let’s connect on social media! I’m @courtneykocak on Twitter/X and Instagram. For more, check out my website courtneykocak.com.
 | A guest post by
|
Oh, wow, thank you, Courtney!! I am excited to revisit and share this. I am grateful!