Why I switched back to Substack

I’ll miss owning the branding and design of my creative work but this is the right move for us right now.

Substack first entered my consciousness in the fall of 2018. I’d discovered (and become obsessed with) Popular Information, a newsletter about politics and power by Judd Legum, the former editor-in-chief of a progressive website called Think Progress. So I spent the previous three years — the “lost years” as I like to call them — in a sort of digital wilderness, haphazardly creating infoproducts and accepting consulting and copywriting gigs to make ends meet and make me feel less like a loser in the status-driven terrain of New York City.

By this point, I had all but given up on being a professional journalist despite rising to the top of my industry before I turned 30. But I can’t swim so I knew it was time to hop off corporate media’s sinking ship before being assigned another listicle drowned me. I also recognized my patience isn’t set up for the freelance game of waiting weeks — sometimes months — after a published byline to receive last month’s rent money.

And Legum seemed to thrive with the freedom that came with directly writing to an organic community of readers, some of whom paid him to do so. It was early so there was no way to be sure of this model’s sustainability. But there was little doubt that the idea of a tiny subscription media business had major promise. And although I was a satisfied reader, I was also a curious writer who had to know more about the company behind the technology that made it all possible.

Substack set out to solve a problem I lived through first hand: media’s musty business model. This week five years ago, I was laid off from the dreamiest of dream jobs as digital fashion editor and style columnist at Lucky. At any given moment, you could have found me popping into a showroom for an up-close-and-personal survey of a designer’s latest collection, coordinating schedules with a publicist for a profile, researching clothes and accessories to feature in one story, writing style tips for another story, sweeping the news for celebrity style inspiration, Slacking my coworkers a Beyoncé gif to illustrate my current mood or schmoozing with colleagues at an after-work press event. As much I miss the work, it’s those colleagues I miss the most.

By the time I arrived at Lucky, its publisher Condé Nast, which is also the corporate steward of media stalwarts including Vogue, Vanity Fair, GQ and Glamour, was already in administering our magazine’s slow, painful death. We had layoffs as often as pitch meetings, it seemed. We merged with a west-coast e-commerce company to make all of our content shoppable. Remember when everyone “pivoted to video” a few years ago? Lucky hopped on that bandwagon too when it partnered with another west-coast startup to zhuzh up their video content with our editorial expertise. But nothing seemed to replace the advertising revenue that led to the pre-internet prosperity so many of the aforementioned magazines enjoyed. And they ran out of money before we were the casualties.

Substack’s main attraction is its simplicity. In a matter of minutes, writers are equipped with everything they need to start a premium publication: subscriber management, built-in payments that enable recurring subscriptions, and a text editor to publish web and email posts with rich text, audio, photos, gifs and embedded media from social apps.

This simplicity is also what motivated me to switch in early 2020. Writers are locked into a single basic design and unable to customize the look and feel of their website or emails. I’ve spent more than a decade developing a visual identity that can enhance the look and feel of my words. Obviously, this one-size-fits-all approach was a turnoff. But as long as the lack of custom branding is non-negotiable, the alternative is to outsource web hosting, email delivery and payment processing to three different apps, which comes with its own imperfections as you can imagine. (My current workflow requires me to hack annoying workarounds for essentials like group subscriptions, gift subscriptions and discussion threads that are native to Substack.)

And as I continue to nurture The Supercreator, Substack’s writer community and halo effect are also meaningful assets. In the span of Donald Trump’s first term in office, Substack has branded itself as a safe space for writers to go indie and connect with each other. (It has even made newsletters shorthand for all manner of premium writing on the internet like blogs were a decade or two ago.) I’m intentional about operating a tiny one-person media business, but I’m also aware of the value of participating in a community of professionals who do what you do. If independent writers are a club, then writing on Substack is the cover charge for entry. And I’d like to work less hard to find my people than I’ve had to since I left Substack last winter.

With all this said though, I’m not beholden to Substack. As I’ve written before, social apps are excellent discovery tools but none compare to the stability and sustainability of owning the channels — email, SMS, blog, RSS feed, for example — that directly connect you to your community and enable you to deepen your relationship with it. Web Smith sums it up perfectly: “If the audience is unable to move with you, then it probably will have a return date at some point,” So since my email list and Stripe account are portable and my editorial strategy is proprietary, I feel empowered to do what’s best for me and the subscribers I’ve chosen to attract and serve.

While this sounds like a love letter to Substack, the company itself is imperfect. Its superstars are mostly white or white-adjacent. But so are corporate media’s A-listers, which says more about how homogenous the corporate-to-indie pipeline than it does about Substack itself. And there are several commercial considerations that impact how successful writers and are outside of Substack’s control. Still, it would be nice to read a news story about a writer of color quitting their high-profile media job and going indie with the support writers like Casey Newton of Platformer and Emily Atkin of Heated received from Substack to strike out on their own.

But it’s hard to root against a company that seems to be trying. In the past week, Substack announced product updates that enabled writers to customize both their post’s URL to optimize for search engines and the preview images that are displayed by social apps when someone shares their post. On a personal note, the ability for writers to add a custom domain to their Substack was what made me reconsider switching back. Plus, I love Substack Defender, a legal support program that was introduced in July provides pre-publication legal review of individual stories and responses to cease-and-desist letters for writers. Substack has also joined an initiative to address our climate crisis. And a healthcare offering and system to connect writers with editors are in the works too, two benefits that keep writers at media companies even if their ambitions would have them do their own thing otherwise.

So just in time for The Supercreator’s first birthday in exactly two weeks, I’m back on Substack. I’ll still continue to report on how to reimagine the new economy so it works for all of us with curiosity, skepticism and fairness. I’ll keep telling stories that help you make sense of not just what happened but also what matters. And it’ll be easier than ever to participate in community discussions on the topics and issues that matter to you so stay tuned for those. Because no matter where my work is published or how you interact with it, one thing is for sure: You deserve to get noticed and paid for the brilliance you bring to the world. And you can count on me to keep showing up with insights to make it possible.