Dear Writer: Advice on writing like it matters

On following one playbook for a writer that can make the most sense: a lifeline

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 above.

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 with a different voice that felt closer to my own. Here, I started to test out what it might feel like to write instead of catch eyes. Here, I got honest in a way that I don’t think I’d been anywhere else. Here, I started charging for my words, daring to believe that my writing wasn’t some side project but the main event. In 2021, trying to figure out what to do with the rest of my life, I thought “maybe writer.” Some 50 Substack essays later, I think “writer.”

What has been so delicious about writing on Substack is that it isn’t something that fits into my wider writing practice, like some piece of a puzzle—it is my writing practice. Writing here also isn’t something that fits into my wider online presence, because in being here, I have learned that an online presence isn’t something I care to curate the same way I once did, if at all.

Read more: #1 Being All Of It

I think we ask people things like I am being asked because we want to know the formula, the juice, how to replicate or establish or build. We are conditioned to believe that it doesn’t matter unless there are clicks, impressions, likes, comments, engagement; that our work doesn’t matter unless we’re known. I’ve been successful in the measurable ways because I followed those playbooks, but that has always left me miserable. Here, I have not followed the playbooks, I have done a lot of it wrong, but I have written like it matters, like what I have to say matters. If there’s any advice I have to give, it’s that. Sure, pay attention to the technical bits, the hacks and the best practices, and drive your engagement and whatever. But write like it matters and like what you have to say matters. Write like it’s 2013 and no one knows who the hell you are or cares what you have to say, and do it anyway.

Sincerely and truly yours,

Holly Glenn Whitaker

Subscribe to Recovering on Substack, and you can also find Holly on Instagram and her personal website.

This is the ninth in a recurring series of longform writer advice, following Lucy Webster’s advice on writing from personal experience, Scott Hines’s advice on cultivating connection in the internet age, Robert Reich’s advice on sharing your personality, Helena Fitzgerald’s advice on isolation, Alicia Kennedy’s advice on learning to listen, Kate Lindsay’s advice on creating trust with your readers, Anna Codrea-Rado’s advice on learning to celebrate how far you’ve come, and Mason Currey’s advice on creative growth.

Could you use some advice or inspiration from a fellow writer about creativity, motivation, and the writing life? Submit your question for consideration for a future advice column by leaving it in the comments below.