Dear Writer: Advice on writing like it matters
We asked Holly Whitaker to share advice on her writing practice. Holly writes Recovering, a newsletter that looks at recovery as a way of living that is accessible to everyone. Holly started blogging in 2013 after going sober, which turned into a sobriety school, a digital recovery startup, and New York Times bestseller Quit Like a Woman. She is also working on her second book and a podcast. Read on for her advice, or listen to her read it aloud. Dear writer, how does your Substack fit into your wider writing practice and online presence? Before I knew I was a writer, I was an accountant. My job title was Director of Revenue Cycle Management Operations, and the only essays I wrote were soul-destroying emails I cc’d your boss on. If you would have told me back then that one day I’d be explaining how something called a “Substack” fits into my “writing practice” and “online presence,” I would have done what I did the other night at a comedy show, which is spit on someone. Because of laughing. But that’s where it started. I was wearing lots of Ann Taylor Loft and formatting spreadsheets by day, and by night—because I was newly sober and exploding inside and having to pretend everything was normal over here, and there was nothing to see, folks—I wrote for a WordPress site, anonymously. I start my answer there because that’s where it counts and what I want you to get from this answer. I didn’t start writing to build an online presence or even to have a writing practice, but because I needed to write. I had to write. I didn’t know what else to do. I was lost. I was alone. I was stuck in the wrong life. I had a lot to say and I didn’t know who to say it to. That was 2013. “I didn’t start writing to build an online presence or even to have a writing practice, but because I needed to write. I had to write.” In 2021, by then a New York Times best-selling author and someone who had been featured in Vogue multiple times and had sold hundreds of thousands of books and counted among her assets a very loyal and large social media following, I grabbed a Substack handle for the same reasons I secured that WordPress domain way back when: I was lost, I was alone, I was stuck in the wrong life. I had a lot to say and I didn’t know who to say it to. What I mean to tell you, fellow writer, is that I didn’t start a Substack as a strategy, as a way to hone my writing chops or build a brand or make a living. I started it out of desperation, as a lifeline. Much like 2013 and the now-defunct littlemisssurrendered.com, Substack was the only thing that made sense, and even that makes it sound like it was more planned than it actually was. When I say I was lost (in 2021), I mean I was not sure what I stood for anymore. I’d recently been squeezed out of an organization I founded; I’d lost many of my friends; I lived alone in the woods on a dead end road, and my cat was who I talked to the most, and my identity was hanging in a closet somewhere. My head was a soupy mess of ideas, and my thought loop was nihilistic, and everything I believed in felt fraught, and I was scared I’d written myself into a corner or that maybe I had peaked and it was all downhill from there. Back then, the thing that felt so great about Substack was that it wasn’t some blog people might attend or even a Mailchimp that might turn into a sales pitch. Substack was a place where readers had to figure out how to sign up, a place where they had to agree to get your emails on a regular basis, a place with barriers to entry, (in some cases) a cover charge, and those things were not available on social media or a blog site. People had to want to read me, effort to read me, and in some way all that made my writing holy again. It created a boundary, a haven, a netting between myself and the scant few that might follow me here from places where I was more well known and my art was consumed in the blur of a scroll. Here, I started to experiment
