On The Rush To Greener Pastures, and Writing For Substack

A Substacker giving their thoughts on Substack, how groundbreaking, but stay with me here...

Since I wrote my trio of pieces detailing the Substack Pro controversy, the trend of writers and publications opting to start Substack newsletters has kept chugging along. Among the latest to make the switch are Charlie Warzel leaving the New York Times and Arc Digital leaving Medium to join Team Substack. 

I was inspired to write this piece after reading Jack Shaffer’s excellent piece for Politico detailing the shift taking place in journalism, with talented writers leaving behind the drudgery of working for a media outlet for the footloose and editor free life of a Substack writer. I’ve already shared some of my thoughts on what this could mean for both writers and media outlets but I want to expound on those and take it a step further by giving my feelings on the Substack Pro controversy and on being a Substack writer.

Watching the whole Substack Pro controversy devolve into a petty temper tantrum over who was getting paid how much was hilarious. Finding out that Substack outflanked their critics by grossly overpaying Danny Lavery and his wife Grace, and that they both happily took their Pro deals, had me cackling in public. I will always be amused that a dumb, manufactured controversy over Jesse Singal and Glenn Greenwald having Substack Pro deals when neither one of them does is the thing that is causing the biggest shakeup in journalism in decades. 

There is also a visceral glee in knowing that people like Bari Weiss and Andrew Sullivan, who were forced out of their jobs by people who couldn’t abide their centrist views, have gone on to make exponentially more money than the people who forced them out. Call me petty, but that is deadass roll on the floor funny; I wish nothing but success to them and every writer in their boat.

It is not just the big-name writers who have found a home on Substack -- Issac Saul, the founder of Tangle, has made the leap to writing for Substack full time due to the popularity of his newsletter. Saul’s story is inspirational; when he started Tangle he was an out-of-work writer who was unhappy with the state of political journalism, so he sketched out a newsletter concept where he would offer a balanced take on one issue a day. Now, after almost two years, Tangle makes enough to support Saul and a staff. The success of Tangle shows that even without a grant or Pro deal a writer can be successful on Substack.

As for myself, I’ve enjoyed writing for Substack. While I nabbed the Jen the Libertarian Substack name back in May 2019 I didn’t start writing on the platform until September 2020. I’ve done alright, had a few pieces go viral, had some tremendous help along the way, and have generally enjoyed my time here. I enjoy the freedom to write about whatever interests me, and as Shaffer points out, not having to pitch ideas, get approval, go through the editing process, etc is nice.

I will say however -- writing for Substack isn’t for everyone. For a writer who is used to working for a publication, with the deadline schedule that comes along with that, transitioning to a more freelance type of schedule can be rough. It takes a lot of discipline to create and keep a writing schedule, and I can say there are days when I wish I had an editor who emails me an assignment in the morning, and then all I have to do is fulfill that assignment. Being a one man (or one woman) band means having to do everything yourself, from generating ideas to research to writing to fact-checking to editing to writing a headline to picking artwork to go with your piece. Don’t get me wrong, this is a fun job but it is a job and it takes a lot of time to do it all yourself. I can understand why a writer would rather work for a mainstream publication, especially since those jobs look much better on a resume than being a Substack newsletter writer. 

I remain curious as to what Substack will look like in a year, three years, and five years from now. How many more top-tier writers will make the leap? Will Substack produce superstar writers the way the blogosphere did? Will those writers stay on the platform or move to legacy media jobs? Can legacy media financially compete for talent with Substack? It will be some time before we get answers to any of those questions but right now, it’s a damn interesting time to be a writer.