How I Grew My Substack from Zero to 40K Annual Income in Just 12 Months

Part One of Two: Where I Started, What I've Done, What Worked Best & What Didn't Work (& tomorrow, the more philosophical "Eleven Urgent & Possibly Helpful Things I've Learned Along the Way")

As promised, today’s post—which would normally be a Monday Lit Salon post, so that’s how we’ll tag it!—is about how, with little platform and no significant email list, I built this Substack to more than 4000 subscribers, 700 paid, and 40K annualized gross revenue in just 12 months.

Read Part Two of this post here.

The short story is, I worked hard. As

Summer Brennan

said in

A Writer's Notebook

last week, in a beautiful and deeply wise post about writing and the creative life and success on and off Substack:

Here’s the important thing, even though it can be hard to hear: no writer, no book, no essay or post, is entitled to be read. No one is entitled to success in their writing, and notable success in writing always takes a lot of work. No exceptions.

This is the guiding principle of my artistic life. I call it “investment without attachment,” which means, we do the work consistently and well, tirelessly, doggedly. And we focus on that—the work, and the quality of the work, because that’s what we can control—not the outcome of the work.

But it turns out that story, the longer story of how I’ve applied the principle of hard work on Substack, is longer than I expected, especially once I wove in the questions you all shared with me yesterday. So long, in fact, that this post is too long for email, so if the newsletter is truncated in your email, you might need to click on "View entire message" in order to see the entire post in your email app. By the time I was finished feverishly writing last night, I had more than 10 pages in a Word doc! So, I’ve been trimming it down and am sending it out over two days, Part One today and Part Two tomorrow. If you find typos, I can only sigh at this point.

Today, I bring you a careful review of the concrete specifics, including:

• Where I was when I started Writing in the Dark last December

• What I’ve done since then to build the newsletter

• What’s worked best

• What hasn’t worked

Tomorrow, I’ll send out the more philosophical and artistic assessment, which embroiders the threads of my brightest thoughts on the eleven urgent & possibly helpful things I’ve learned along the way (and, yes, I chose the number eleven because my first “popular” and a little-bit-viral Substack post was my Eleven Urgent & Possibly Helpful Things I’ve Learned from Reading Thousands of Manuscripts, which I published last December; it was picked up by Brevity and shared quite a bit on X/Twitter and is still my most popular post of all time, a year later. So, eleven lessons it is!). Today’s post, meanwhile, is a truthful, open, and transparent account of making an income on Substack as an artist (specifically, a literary writer and teacher), including what has worked and what hasn’t.

Disclaimer (in case you missed it in yesterday’s teaser): Audience size and/or income are not the end all be all and in some cases just don’t matter. There are a million ways to use Substack, a million reasons to write, and a million paths from which to approach writing, including for self-expression and plain old fun.

I happen to be a professional writer. I’ve been publishing since my early twenties and have worked in writing or writing adjacent jobs, including teaching, my entire adult life. At twenty-two, as a brand-new mom, I was a stringer for the Chisago County Press, earning twenty bucks a story for covering the city council and school board—and, yes, I had to attend the meetings. I’ve written hundreds of magazine articles and essays and about a dozen small-time books as a ghostwriter. I’ve written scads of state and federal grants and even more internet “content” (thank god those days are over!). I’ve written a children’s picture book and several educational books. I’ve worked for a cumulative total of about a decade as an editor at magazines. More recently, I’ve been employed as a writer and writing instructor at the University of Minnesota School of Public Health, where I teach Writing for Public Health and facilitate narrative health workshops. And I finally busted out with my own literary debut—a memoir, The Part That Burns—in 2021 at the age of 53. I should add that I’ve also been teaching creative writing for more than a decade, and that, despite being a college dropout, I managed, in 2015, to get myself into an MFA program at Vermont College of Fine Arts, and came away with an MFA in fiction in 2017.

It’s no surprise that I approached my Substack as part of my career and my identity as a professional writer and writing teacher. Unless I am volunteering or doing something as part of the free promotional work most writers do, I am generally paid at least a little for my writing and teaching by the venues where I work. So, I approached Substack with the same expectation. But that’s not the only way. There are many ways; I chose what felt right for me.  

And for the deep-divers here, I’ve written before about my philosophy around building this Substack (and the community it represents) for Brevity, in a two-part post that ran last June called What Substack Taught Me About Nimbleness, Improvisation, and the Absolute Necessity of Mistakes (part two is here).

Also: despite the headline, today’s post is not primarily about metrics (I don’t like or enjoy metrics and I avoid looking at them as much as possible). This post is about passion and alignment and how I’ve been able to do what I love and am best at (writing, and writing about writing and creativity and the challenges of living a genuinely creative life, including my own creative life, and sometimes in a deeply personal way) right here on Substack. It’s been a wild, fast-moving year.

So here we go. Please feel free to share your thoughts and questions in the comments so this can be a conversation, which is always my favorite thing for a post to be.

Where I Started

1.     I had a clear vision.

I launched WITD a year ago after wanting to launch a Substack for at least two years and counting. I was an avid fan of Heather Cox Richardson before she migrated to Substack and launched Letters from an American, and she was the reason I first came here as a reader. Note that she is also the most successful Substack writer of all time, in the most successful Substack category (politics). Creative writing is a tougher sell, but by no means impossible. I soon became a subscriber to

Suleika Jaouad

’s Isolation Journals and

George Saunders

’s Story Club. Ah, writers writing about writing! I know I will not likely ever achieve the fame of Suleika Jaouad or George Saunders, even if I do manage to finish my novel, which I am hellbent on doing this January and February. But, still, writing about writing and what it means to “do language” was something I felt I could do well, and do a little differently from what I’ve seen done before. It got me thinking about what I might have to say, and how I might contribute. It got me excited to participate and be a part of something larger than myself. And that’s why I started my Substack.

2.     I had a very small email list.

I started with a mostly defunct email list of 600 that I had been collecting since 2012, when I put up my first Squarespace website for Elephant Rock, the independent creative writing program I founded back then (which is now its own small but mighty endeavor). By passively, I mean that people clicked the “sign up for my newsletter” link on my website and typed in their email addresses. However, there was no consistent “newsletter” before Substack, despite my best intentions. Instead, I sent out informational posts a few times a year when I was offering retreats or workshops through Elephant Rock. So, of those 600 or so emails, only about 100 belonged to people who really did/do follow my work. The rest, not so much. That is why, when I launched Writing in the Dark via Substack last December, I did import that list, but I also included prominent, upfront info early and often explaining what was going on and making it easy for folks to opt out and unsub. The last thing I wanted was to annoy a bunch of people who didn’t want my emails!

I also knew—and this feels important—that despite my lack of platform, I could count on the 100 or so people who really did care about my work to check out what I was doing on Substack. They way these people showed up for me during my book launch in 2021 made their investment in my work very clear. They showed up with love. I knew that if they checked out my new newsletter, that might value it enough to stay around awhile, since they had valued my work in the recent past.

3.     I had a small social media following.

I had a comparatively small social media following, mostly on Facebook, because I’m 55 and never really got traction on any other platforms. I have fewer than 4K Facebook friends, 1K Insta followers, and mostly an echo chamber on X/Twitter, because I was late to that party and generally too sincere to stand out there. I did, of course, announce my Substack’s launch on social, but I only occasionally push my posts there, because it doesn’t do much and would start to feel obnoxious given that I post three to five times a week.

4.     I had a ferocious work ethic.

My debut memoir, The Part That Burns, was published by a respected but tiny micro indie press (Split/Lip) in 2021 at the height of lockdown. Having waited my entire life for my literary debut, I was committed to doing everything possible to give my little book a shot at not being dead in the water on pub day. This is not a post about indie book launches or promo (maybe another day), but what I learned from launching The Part That Burns is that it works if you work it—a lesson my life had already taught me. I grew up hard scrabble and in foster care, and have been working to support my own needs since I was fifteen. I recently found some county foster care documents where my mom actually recounts me working to support her financial needs. I know how to work hard. And while TPTB was by no means a bestseller, it did get wonderful (starred!) critical reviews and, over time, it garnered a small but mighty fan base, especially among literary writers, who are, in my opinion, some of the most supportive friends you can hope for. I came to Substack prepared to work hard, and in the end, it might be the combination of a clear vision, a tenacious work ethic, and a very warm heart that have helped this newsletter grow as it has.

What I’ve Done

1.     I knew my niche.

I launched a Substack newsletter with the aim of writing about writing, and teaching writing. As mentioned, my inspirations at the time were George Saunders (I am a rigorous and honest teacher, and so is he, and I see writing as a way of living, and so does he) and Suleika Jaouad (she believes so passionately in creative community, and so do I, and she believes that art can both save us and connect us, and so do I).  I still kind of see Writing in the Dark as the little baby Substack you might get if Story Club and Isolation Journals fell in love. Anyway, I was crystal clear on what I wanted to offer, what I wanted my Substack to be.

2.     I got help to launch.

I’d wanted to start a Substack for a couple of years without managing to do so (my work schedule is overwhelming), so I knew I would need help to make it happen. I hired Liza, a former student (we now use the title “program manager”) for 5/hours a week to help me get things rolling. Chances are, if you’ve emailed me about some kind of subscription problem, I’ve called on Liza to help you. Thank god for Liza.

Once Liza did the tech stuff, I had to craft the About language (which I obsessed over) and all those welcome email missives explaining not just what I was building, but, more importantly, how to opt out of it. The last thing I wanted was to have a bunch of people mad at me for suddenly emailing them all the time several times a week (I’ll get to my publishing schedule in just a second) when before I had only emailed a few times a year and they might not even remember who I was!

3.     I determined my posting schedule and features.

I knew I would do weekly writing exercises, because I was already doing that on Patreon. But I was trying to move away from Patreon, because the model wasn’t intuitive for me. I’m an unknown, long-form literary writer and aspiring novelist whose work takes forever to produce—how would I really attract more than a handful of supporters on Patreon? I was shocked that I even had any at all, but I did—I had about 30 generous patrons for whom I was offering certain perks, from writing exercises to glances at work-in-progress to Q & As and more. But what I wanted was to move all of that to Substack, where the Patreon people would get everything they’d been promised and more, but I could also appeal to a wider group of readers. And where monthly contributions/subscription fees could be very small individually, but substantial in total.

4.     I had a paywall from the start.

At first, the weekly writing exercises (now called Writing Lab + Prompts) were my only paid posts—and I paywalled them immediately because my Patreon supporters were already paying! It didn’t feel ethical to those loyal supporters to give away for free on Substack the perk they’d been paying for for almost a year on another platform. But I also wanted to provide valuable free writing on Substack in order to establish my voice here, earn readers’ interest and trust, and gain a wider audience. So, I published the Writing Lab posts every Wednesday, and they always included a free introductory craft essay, usually based on a close read of a published poem or essay or story (not unlike what George Saunders does on Story Club). The associated writing exercise that followed the craft essay was paywalled, and something people could work (or not) on their own. (By the way, writing exercises as I define them are more involved than typical writing prompts, which are generally brief and open ended. In contrast, Writing Lab exercises are generally multi-step and constrained. People say they’re life changing in terms of waking up their writing, and I don’t think that’s hyperbole.)

To note, sending the Writing Lab post out to everyone with the craft essay free and the exercise paywalled is not a gimmick to get readers to hit subscribe at the paywall, although of course that does happen. Instead, it’s a way to offer consistent, valuable content to free subscribers, while reserving the actual exercises (all of which I carefully construct myself) and the participatory and interactive comments section for paid subscribers. This has been working very well for Writing in the Dark.

Here are two bits of feedback I’ve received just in the last 48 hours about my free content:

I just want to pop in to thank you for your Substack blog and to say again how much I admire your work and your teaching. I am not a paid member right now, but I still get a lot out of it, especially all those amazing pieces of writing that you link to illustrate your prompts and ideas. 

Happy Birthday, mother of Writing in the Dark! Even before I was a paid subscriber, I learned so much from the tips and wisdom you so generously gave us freeloaders. :) I think it's that generosity combined with your love of people, love of craft, and your hard work, that helped your Substack grow so quickly. ❤️

So, yes, I give a lot away for free, and I greatly value and appreciate my free subscribers and want them to feel excited about what they find here, even though my regular features (Monday Lit Salon and Wednesday Writing Lab) are paywalled, and my seasonal intensives (more on those later in this post) are as well. It’s possible to be very generous while also having paywalls, which is what I choose to do.

One more thing about the early days: once a month, I’d write a longer, structured newsletter called Margin Notes. As for how that went, I say a bit more about it in the What Didn’t Work section of this post.

5. I had an early and (sort of) viral post & some publicity.

In December 2022, the same month I officially launched Writing in the Dark, I taught a writing retreat in Mexico—it was a manuscript revision intensive through Elephant Rock—and I came home with my brain on fire with all the recurring writing patterns I’d been immersed in during that week on the beach. My head was spinning and my heart was racing to write a post as fast as I could just in order to capture all those fast-swirling thoughts. So I did. I wrote a post, and sent it out. The next morning my subscribers were blowing up. It turned out Brevity had picked up my post and it was going very mildly viral on Twitter. I definitely got a few hundred new free subscribers (which was a lot for me at that time—the Brevity post boosted me up over the 1000 total subscribers mark by January and earned me a check mark for paid subscribers as well). More importantly, though, that Brevity post showed me that the readers here on Substack were genuinely interested in my approach to teaching writing. They really appreciated my Eleven Things post, and resonated with it. They said so many amazing things, things like:

“This is the best thing I’ve read all year on creative nonfiction! I feel like I’ve taken an entire class just reading this!”

The outpouring of feedback gave me a tremendous rush of energy to expand and refine what I was doing with Writing in the Dark over all. Even Dinty Moore emailed to say “surely there is a craft book here.” Not long after the Brevity post, Writing in the Dark was also touted in Electric Literature, Write Minded, Writers Bridge, and Lit Hub, all of which kept the momentum going through January and February.

6. I took a risk that brought the most subscribers (by far).

Getting a little publicity was super exciting and definitely helpful—but the absolute most helpful thing by far, hands down, was when I took the risk of offering my own direct teaching on Substack. I did this by inventing what I call my “seasonal intensives,” an idea I dreamed up to make my Substack more interactive. I love a vibrant creative community. So, without knowing whether it could work, I began offering direct, interactive writing instruction on Substack to build community. During seasonal intensives, I post (on a set schedule) a structured, scaffolded curriculum that I create especially for Substack with the intention that readers can respond and interact in the comments. In 2023, I led two of these seasonal intensives—the April 30-Day Creativity Challenge, and the fall Essay in 12-Steps Challenge, which ran August – October. And, this Wednesday, WITD’s third seasonal intensive, The Story Challenge, launches (and will run through February).

In terms of growth, the April Creativity Challenge brought in at least 100 new paid subscribers. The Essay Challenge brought in more yet, and the Story Challenge is set to do the same and more again. I have learned that people really enjoy the structured curricula and the direct guidance (I am very present and participatory in these intensives). And the intensives are indeed intense. I am a rigorous teacher and really believe in the power of language to change us and change the world. Apparently, Substack is a good place for that kind of energy!

Writing in the Dark seasonal intensives are a major factor in the growth and vibrancy of this community—but that doesn’t mean interactive teaching is the key to growth on Substack. Heather Cox Richardson doesn’t do a single seasonal intensive, and she’s the most successful person on here. The point is to do what you do best. I teach best. So, that’s what I do here.

7. I experimented and invented new features.

Posting frequently has worked well for Writing in the Dark—every post, free or paywalled, tends to garner between one and five or so new paid subscriptions. So, I decided early on to increase my posting from once a week to several times a week (like George and Suleika!). That’s partly why, in July, I invented Lit Salon, the WITD advice column. Lit Salon is a joy to write and it seems that readers really like it too! I get to answer questions about all things related to creative writing and living a more creative life, which is fun for me and allows me to meander into some territory that’s less about writing and more about life’s other mysteries, which feels good. I love Lit Salon.

Finally, because Writing in the Dark grew so much and so fast during the 12-Week Essay Challenge, we launched a From the Archives feature in November in order to share archival posts with new readers. A weekly archive feature is easy and makes sense with my richly resourced archive.

8. I consulted with Writers at Work.

In September, I reached out to the incredible

Sarah Fay

of

Writers at Work

and hired her for an initial session and then a three-pack, of which I have one remaining session to complete. I highly, highly recommend her for anyone serious about building their newsletter with more ease and less frustration. Sarah is brilliant and knows Substack inside out. When she heard that one of my main goals was to build community, she recommended that I change the subscription tiers (raise monthly rates and lower annual rates, and introduce a founding plan for just slightly more than the annual plan but still less than paying monthly, with more interactive content like Voice Memos, Video Notes, and Live Salons on Zoom). I followed Sarah’s advice, and am definitely seeing more people choose annual and founding plans than monthly, which really, really helps when you’re trying to build community because when people stick around long enough to get to know me and each other, something more than a newsletter can start to happen. Or, at minimum, people have a chance to open more emails and discover that they actually value them, which improves retention and, thereby, a community vibe.

What Worked Best

• Seasonal intensives have been, by far, the biggest driver of growth for Writing in the Dark. These intensives—the Creativity Challenge, the Essay Challenge, and now the Story Challenge—combine my craft writing with interactive, individualized teaching, which readers have loved (and that’s great, because I love it, too). The seasonal intensives affirm that in addition to writing, my purpose in life is teaching, and that it can be done on Substack, too. In other words, what’s working best is being who I am: a writer who teaches writing.

• Taking the newsletter very seriously from the very start. I pour my whole heart into it—and a lot of time and work. I have spent several hours—maybe about seven? eight?—so far just on this two-part post. It’s hard to track because I work in bursts around myriad other professional demands and familial care (my granddaughter’s birthday party was yesterday! My son came for dinner last night!). The time and effort it takes to build the newsletter varies week to week, but it’s significant.

• Doing what I say I will do. This starts with clearly stating my publishing features and schedule and sticking to it—and updating my description every time I change what I’m doing. I am a person of my word, a person who respects other people’s time and money, and a person people can trust. This matters to me.

• Building Community. My years of teaching come in handy. I read every comment and I respond with care. I really care. I answer emails. I am warm not because I think it will get me more subscribers, but because I am naturally warm. I let my warmth shine here. I was an elementary and middle school teacher for ten years. I learned so many things teaching children and adolescents, including how vulnerable we all are deep down. Once I learned that, I began learning how to really listen, how really to see. I apply those superpowers in all of my work in all arenas, including on Substack.

• Experimenting and staying open to change. I’ve redesigned the Substack several times and changed the tagline, too, plus added and subtracted features and changed up how I format posts, etc., and rewritten subscription benefits. Change is fine, as long as you know why you’re making changes and are transparent and direct.

• Lit Salon! This feature offers me the chance to write about things that don’t fall neatly into the “writing teacher” niche. It’s more about living in the world as a writer than about writing per se, and that gives me latitude to explore dusty evening corners and strange morning light. Lit Salon is more personal and meandering and less defined than Writing Lab posts or the seasonal intensives, and, because readers write in, it’s still interactive. It gives me a place to write expansively, and I love it.

• Paying for help. I knew I needed help (as I said, we call Liza a “program manager” though we could also just say “hero”). Liza still helps 5 hours a week on all the technical stuff I’m terrible at. And when Writing in the Dark started exploding back in April with the Creativity Challenge, I also began paying my youngest adult child,

  Billie Oh
  , who is also a writer, a 5-hour/week stipend to help me with newsletter tasks—everything from redesigning the homepage to figuring out how to rework subscription tiers to helping with the posts themselves. Having help makes all the difference. In total, I pay $800 month for assistance from Liza and Billie, and it is worth every penny. Having help is the only reason I have been able to focus almost solely on writing the newsletter, rather than managing it through all the other tasks associated with keeping it running, tasks that would quickly drain my energy, spike my stress, and turn something creative and good into something I would wholly dread. My decision to invest in having reliable help is a big part of why Writing in the Dark has grown so fast—it’s less lonely and I get to reserve most of my attention and energy for the writing.

What Didn’t Work

• The Margin Notes monthly newsletter just didn’t work. I found it a chore to write and, too often, redundant with things I’d already planned to write or was saving for later. It was too structured, too much of a formula. I just didn’t like it. And I’m an Aries. I don’t like to do things I don’t like to do! So I eliminated it and told my readers it was going away. No one seemed to care, which confirmed my instincts. This was a good lesson for me—that we can let things go, and that sometimes, we very much should!

• The 30-Day Creativity Challenge both worked, and didn’t. I mean, it brought in more than 100 paid subscribers in a fell swoop, almost doubling my paid subscriptions when my newsletter was under six months old. Obviously, I am wildly glad I did it! It was a tremendous success in terms of growing the newsletter and fostering community. Writers wrote to me to say it fundamentally changed their understanding of what it means to write—and in a good way! People really loved it. But in terms of how it went for me as a human, it nearly killed me to keep the pace of producing that much intricate, high-quality content on a daily basis. I overestimated myself and it made April a whirlwind of late nights and early mornings. Also, it was rather demoralizing to see how, when the 30-Day Challenge was over, a noticeable number of paid subscriptions dropped off in May. I don’t remember exactly how many—maybe ten? fifteen?—but it felt like a lot after just having just worked so hard! I felt a little … frustrated when folks dropped off after paying only $6. But I don’t believe in entitlement, so I knew my frustration meant I needed to look inside, not outside. After reflecting, I switched to 12-week formats for seasonal intensives rather than repeating the 30-day format I’d used in April. I wanted participants to stay around long enough to get invested in what we’re doing here—to experience the cumulative nature of creative work, how it works in us and between us. So far, that shift has been awesome. I loved the Essay Challenge and worked my butt off without ever feeling frustrated, and there was no notable drop-off in paid subs when it ended. But also, if you’re new here, you really should dive into the Creativity archive! It’s a rich resource and, um, have I mentioned I worked really hard on it?

• The chat didn’t work super well, mostly because Substack rolled out Notes so soon after the chat, and, meanwhile, I was also building community in my comments sections. Participation felt too spread out. We can only be in so many places at once—so, I dropped the chat, more or less. I mean, I still have it, but I told subscribers that I’m not really trying to amp it.

Love,

Jeannine

Note: You can click here to read Part Two of this post, the more philosophical side of the last year, with “Eleven Urgent & Possibly Helpful Things I’ve Learned Since Launching My Substack.”

Also, here are those two Brevity posts from last June about growing this newsletter—part one and part two. And please share your questions, comments, and observations in the comments, including your own Substack stories!