Surprising Lessons From 1 Year of Writing on Substack

I actually really love you guys and also I'm never going to publish every day

Sep 12, 2023

One year ago I decided that I was going to pull out all the stops to do what I have always wanted to do, which was to BE A WRITER. I decided I was even willing to—gasp—write online in service of that goal.

I came here naive about the internet. I came with a feeling of resignation, a belief that in starting an internet newsletter, I was giving in to the pace demanded by modern capitalism—faster, faster, faster and more, more, more—but that this is what was required if I wanted to BE A WRITER, which I really did. At best, I hoped the ends would justify the means. Maybe, I thought, I could make a compromise: bring some of myself to the work and also change some of the work to fit the demands of the platform, and in that way work within the system and outside the system at the same time. Maybe I could come here and not completely lose myself. (Losing myself in my career has been a problem for me in the past.)

In other words, I was cynical. I did not do the internet, I was not an internet type of person. I prided myself on this—the purity! The art!—and I also saw the downsides. For one, when my work came out three times a year in print-only magazines with a circulation of a few hundred, it was hard to imagine how I would find my readership, the people who really loved and wanted what I was offering. It was nearly impossible to imagine a path to making any meaningful income. So, at the end of August 2022, I prepared to launch my Substack newsletter. I decided that I would publish at the breakneck speed of twice a month. Imagine publishing twice a month! A breathtaking pace.

Ah, how innocent those times were, one year ago.

As I’ve written about before, Substack did not go as I expected. It was not actually just a big cesspool of market demands that I just needed to keep fighting against (of course there is some of that, which I will get to). Instead, what I have gained from writing on the internet for one year was an avenue to stretch my skills as a writer, genuinely connect with other people who share my interests, and experience an unprecedented feeling of providing real value and having purpose. Color me shocked.

I’d like to tell you a little bit about what I’ve learned here and the growth (both personal and newsletter) that I’ve seen as a result. Then we’ll talk about what’s to come in Inner Workings’ second year!

Exploring fulfilling ways to write

Working on an essay for a year is a fabulously fulfilling process. Drafting it, moving away from it, coming back, workshopping it with other writers, leaving it on the shelf again, circling back again, applying the different perspectives that accompany each of these different periods of work. It is deeply fulfilling to bring something to fruition over many months, even years, and everything I’ve done that I’m most proud of has been made this way.

But—and this shocked me—this is not the only fulfilling way to write! It is also a totally different and awesome experience to try and articulate what’s on my mind this week in the most original and relatable way possible. It is also very cool and different to try and capture new research in an understandable way. It is the utmost fulfilling experience to interview a kindred spirit about a topic of mutual interest and help craft that story in writing. All of these types of writing use different brain parts and different skills, like trusting your instincts (when writing fast or interviewing), doing efficient editing (on everything), and not letting perfect be the enemy of the good (and what perfectionist among us wouldn’t benefit from a little practice on this front).

Here is a reality about Substack writing: there is absolutely no correlation between how long I work on an essay and how much people love it and are touched by it, measured by comments and likes (which of course is just a proxy, but the best I have). I’ve worked on an essay for two years and published it to, more or less, crickets. I’ve worked on an essay for two hours, published it, had it featured by Substack, and got a thousand new subscribers.

The cynic in me would say: “Exactly! This place doesn’t reward the real work!” But the newly enlightened internet writer in me would say: “There’s a certain type of thing that tends to fit here, and that thing is also meaningful and important in a different way.”

Welp. Given that, here are some of my learnings about what works here!

Things I’ve found that fit really well here

Brief personal essays exploring a single topic in an original way, and ideally bringing in one or two perspectives from other thinkers. These offer a digestible dose of wisdom, but not a simplistic one—people here like nuance, yay!
Interviews
Short lyric pieces. This was a surprise to me, and very cool, because there aren’t a lot of obvious places to publish this form.
Synthesis of books, research, and articles

Things I’ve found fit less well here

Complex, 4,500-word personal essays that braid together multiple themes. (Lit mags are still the place for these, IMO! I’ve got one coming out in AGNI this fall that I’m excited to share.)
Longer reported pieces with lots of sources. While some people like these, it seems like they are too long and heavy for the brain space and time allotted to Substack—which seems totally reasonable.

Things I’m not sure about yet

Serialized, memoir-style writing. I’ve done this once, and it seems like there was a core group of people who absolutely loved it, but for most perhaps it was, again, too long.
Podcasts and audio. I’m podcast-curious, for sure, but I’m also careful about how much I’m signing up for so that I don’t dilute the quality. I still care about the quality!

Things I haven’t tried because I hate them

Really short bits of content fired at you every day or multiple times a day. Who cares how good it is, as long as it’s frequent. I hear this is the number one way to build your audience here. I am unwilling to do it, even if it is effective. Especially when wading into territory that can feel compromising, one must have a line.

Real collaboration and connection

As my first year progressed and I began to realize that my goal here was not to publish extensively re-worked literary essays but rather to try new stuff, I also realized there’s no way I could do that alone. Imagine me, sitting alone at my desk trying to come up with new stuff I’ve never done, then trying to do it, and then publishing it to the internet without anyone else ever weighing in. Some people can do this and hats off to you, but I can’t, and this is where my collaboration with a couple key people enabled my first year on Substack to become such a positive experience.

First, I began to exchange writing with my friend and emerging Substack Notes God

Alex Dobrenko`

. Even though we had known each other for over a decade, and even though we had long just gotten each other (despite being very different people), we had never meaningfully worked together. We set up weekly calls to exchange work, which did not end up happening weekly (are you crazy we both have toddlers), but which did and still do happen with a shocking regularity, even now, one year in. Alex never fails to amaze me with his feedback on my work, which quickly gets to the heart of what I’m trying to say and improves it. Perhaps even more importantly, he is someone I can go to with an unworked idea and talk it through. Having that person is absolutely essential for me in this work, especially if there is experimentation involved. He also just always makes me laugh because he’s goddamn hilarious, so yeah…BONUS.

Then Alex introduced me to

Erin Shetron

, whose continuous collaboration helped me spread my wings even further. With Erin, I can bounce ideas and discuss possibilities–what would it look like to do a serialized memoir-style piece? What about publishing this weird lyric essay? What about grouping the work together in themes? Collaborators like Erin can further bring fresh ideas and perspective to the little isolated world of my mind. Again, this is essential to my highest creativity: we can add our brains and together figure out how some little idea might actually turn into reality, like the Lady’s Illness Library. She also helps make my work more polished, both in content and in form, and I like presenting something polished to the world, even if it is produced quickly.

THEN. Then the real thing happened. I started meeting people online that I actually really like and want to be around. WHAT?! I had heard this kind of thing could happen on the internet, but I one hundred percent did not believe it. I know, I know. I was wrong..

This kind of connection mainly happened through interviews, both ones I’ve given and ones I’ve conducted for Inner Workings. During these conversations the internet people turned into real people on my screen, and we had awesome, wide-ranging, and in some cases even life-influencing conversations. One of them is looking for a place in my neighborhood (IRL! Not even in VR!). One of them sent me a book after I mentioned that when I’m knitting I get stressed that I’m going too slowly (long story).

A gift from Kathryn Vercillo. Our conversation about healing through crochet & knitting and much more will be out later this month!

There is also a group of people I haven’t interviewed, but who regularly write beautiful comments on my work, like

and many more. And there are the Substacks I regularly read and comment on, whose authors I feel a kinship with even if I’ve never spoken to them, like

Oldster Magazine

You Are Doing A Good Enough Job

, and

BAD AT KEEPING SECRETS

And all of this together has led me to feel a sense of fulfillment and purpose that I have never felt in my career, not even close. That’s profound. That’s hardcore. Phew. Yeah. I’m definitely thinking a lot about what I was doing for those fifteen years before Substack.

Resisting the pressures to do even more

Even if writing on the internet is way better than I expected a year ago, it still does have traps. I check my subscriber number way too often, most days, sometimes multiple times after I put out a new post (right now the number is 2,357). No matter how high this number, I always want it to be higher, and I expect this will always be the case, and I think that this is the most perfect example of the element of human nature that powers our current late stage capitalist society.

For me, it is a conscious, ongoing effort to not try harder and do even more on Substack, to just not add that new thing, and just not take that advice from some Substack guru swearing that the only way is to publish more, more, more. The fact is, I have already published more, more, more—approximately 400-600% more per month than I originally planned—HELLO, the forces have already acted on me! But in this process I have also been experimenting and finding what feels good in terms of balancing the frequency, thoughtfulness, and polish of my writing. Even with my (drastically) increased pace of publishing, I have at many points declined to do even more. This is all a complex set of compromises and learnings, and I wouldn’t say I’ve nailed it perfectly, but I do feel more confident now that a balance is possible. In other words, I don’t feel that I’ve fallen to my greatest fear at the outset—I don’t feel I’ve lost myself here.

What’s ahead

Whew. Inner Workings Year 2! Time to take all that I’ve learned here about myself and about internet writing and use that to make the coming year an absolute banger for Inner Workings. Here’s what’s coming up! (With the caveat that everything is an experiment and will doubtlessly evolve!)

More thoughtful, succinct essays on relatable topics

The absolute highest compliment I can receive as a writer is when someone says, “oh my god I’ve felt that way for so long and never put it into words, and you articulated it perfectly.” That’s the gold standard for me when I take on a topic in these mini-essays, bringing my own experience, my analysis, and often the words of others. My goal is to present topics in an original way that cuts to some core truth that is hard to reach but feels exactly right once found.

More Lady’s Illness Library

The energy and inspiration I personally get from interviewing these (mostly) women would be enough for me—no one benefits more from this project than I do. But even better, the responses from the community here have been full, multidimensional outpourings of feeling with a heavy dose of gratitude, and I am totally energized to keep this going and build on it. Let’s elevate women (and men!) with chronic illness!

We have four more wonderful, unique interviews in the editing process right now which will come out over the next two months, and over thirty (!) amazing people who have filled out the interest form to participate in interviews. (I apologize to those who haven’t heard from me yet! Your inquiry was not lost!)

Research synthesis & reporting

This is an area where I am still experimenting, but I aim to continue having research and reporting in the mix, covering our favorite top topics here: chronic illness, the microbiome, the nervous system, wealth & power, work culture, caretaking, and the like. I have tried longer deep dives and quick, digestible summaries, and these formats may continue to evolve, with a focus on making the information easily accessible.

Best of Inner Workings

I wrote some pretty rad stuff on here when I had about forty-two subscribers, thirty-nine of whom were my friends (or my mom’s friends). As I take my maternity leave this winter, I will be digging up the gold from the bottom of the pile and republishing it to, hopefully, delight you with some of the past writing I’m most proud of. For the twenty-five of you who have already read these ones…thanks for your patience 😊

Community-building

I have long shied away from using the term “community” to refer to groups on the internet—call it a high-horse thing, given my big life focus on in-person community-building. However, I now cannot think of a better word to describe the emerging connections happening here between like-minded people. I am committed to nurturing that. To date, I do that in the comments section, where I make every effort to read and respond to all the thoughtful stories and ideas that people are generous enough to share. I’m not sure what other avenues will work for us, but I am open to trying them—Substack chat, Discord, Substack threads—expect some experimentation in this area this year!

And lastly…

I just want to express a huge amount of gratitude to everyone who has joined me on this journey over the past year. I feel full and connected in a way that I never have in my life. I feel optimistic and full of potential, things that seemed impossible in the depths of my burnout. I know everyone gets a shitload of emails, and I know it’s no small thing to sign up for yet another goddamn email. So thank you.

Well, here’s to year 2 and all the wild, awesome, and unexpected things that will doubtlessly unfold!

—Rae

I’d love to know…

What are you most looking forward to from Inner Workings - essays on my life in Silicon Valley? Stories about infertility? More about chronic disease and Lady’s Illness Library interviews? Analysis of the newest health-related research?