Consider the Paid Newsletter Writer
And three newsletters that shape me
I’ve written and published 104 posts for this newsletter over two years for free. Before that, I published The Ponder for a year. Before that a client-facing newsletter to support my freelance editing for a year or two. After five years of serial newsletter monogamy, I think I’ve found the real thing with The Good Enough Weekly. To mark the milestones (that are mostly personal) and acknowledge the reality of writing to (try) to make a living, I’m launching paid subscriptions – $12/month or $32/year.
Before Substack was a twinkle in Chris, Jairaj, and Hamish’s eyes, I wrote free newsletters. Mailchimp, TinyLetter, Ghost, and Buttondown. Writing a newsletter was a natural leap from blogging, which I did on Blogger, WordPress, and Tumblr. Sometimes I had more fun trying all the shiny parts of the newest platform than actually…publishing. There was always a reason to write – to practice, to gain clients – that was beside paid subscriptions. I can’t afford to do that any longer, that’s the plainest reason I’m turning on paid subscriptions.
For longer than I’ve written newsletters, I’ve read them – compulsively, and more than books or articles in some years.
The love affair really does begin with The Ann Friedman Weekly, which launched in 2013, the same year I graduated from college with a journalism degree. I was both cranky and delusional. Tired of the posturing and rigidity of the journalism school’s program, and also the beneficiary of its connections through a variety of internships (radio, print, design.) I didn’t want to be a local news anchor, I wanted to be something more glamorous – a magazine writer. And then I moved to small-town WA for my husband’s grad school, where there were no magazines, and reality entered the chat.
I wasn’t called back for a barista job. I was politely declined after an interview for an assistant editor job at the university. In the depths of winter, six months pregnant, I got hired as a morning news anchor at a small radio station – but I told my journalism friends to not get excited. I was pre-recording news briefs that played between ads for burgers and the wannabe-shock jock's headache-inducing live segments. It was during this time I found Ann’s newsletter, right after I had my son and quit the radio job, minting myself a new freelancer. Fridays became The Ann Friedman Weekly day, and the newsletter showed me that something interesting could be built on the internet. No steady job at a glossy magazine required (or feasible).
Remember, this was pre-Trump, during the rise of Into the Gloss, Man Repeller, and before The Wing. The term ‘Girl Boss’ was used unironically. I loved the blogs, but hated referring to myself as a girl so I always felt lost in that arena. Freelancing was hard, and I didn’t feel like a boss most of the time. Ann showed me a way to exist in online spaces as a writer, who also happened to be a woman, and be inviting but not conform. Her newsletter was free, but if you paid you got access to her pie charts – the idiosyncratic cherry on top.
The next newsletter I became obsessive about was The Sunday Dispatches by Paul Jarvis. Instead of newsy updates and links like Ann, it was a weekly essay on topics in the entrepreneur sphere but always with an indie twist. Paul was the first freelancer I really paid attention to who positioned himself as a business owner – but didn’t want to become a millionaire and take over the world. He wrote about wanting enough, he was vegan, he lived somewhere remote. I’ll never forget his subscriber welcome email: It was a story about how he gets a small tattoo of each subscriber’s name, but it’s impossible to find amidst the rest of his tattoos. His newsletter was free, but it felt like a premium product. It was a funnel, leading people to his classes, ebooks, and later an analytics company, and he was open about it. When he published the book Company of One, I bought it in a heartbeat.
While reading Ann every Friday, and Paul every Sunday, around 2017, I transitioned from writing articles to finding small businesses who would hire me to edit or write their websites and other copy. I was tired of hustling to write articles for fifty dollars or churning out four short tech stories in four hours, three days a week, for just under $500 a month. Working the part time hours I had while caring for my now two young children, I never made it into the publications I wanted or knew would pay better. Also, publications were shutting down left and right. I pivoted. Figuring out how to sink my hooks into the business world was a more viable way to make money and opt-out of the personal essay industrial complex that I saw as often manipulative and exploitive.
I’ve always thought I was a strong writer. My area of caution is thinking I’m better than I am, not being crushed by imposter syndrome. Once I had Kindred Word Studio running my ambitions morphed and I wanted more and more everything. The money was good and there were so many small business owners who hated writing or were too busy to do it themselves. I listened to podcasts and read articles that urged growth at all costs and aligning yourself and your business to the point that there was no distinction. And then I’d hit reality again, and those pitiful 24 hours in a day.
Where Ann became a tether to the world of journalism that I hoped to return to, Paul was a voice warning against millionaires as role models. What’s enough? What’s ambition and what’s greed? He wrote about how taking yourself seriously and being a company of one can be a way to find security and stability, rather than go big and burn out. In late December 2020, I opened up that week’s dispatch to find an announcement. The newsletter was coming to a close and he was retiring from having an internet presence. I was so sad, but it made sense. I’m sure he’d been working toward his exit for a long time and I hope he and his pet rats are thriving (his rats featured in his stories and web design).
Less than a month later, in January 2021, I subscribed to From the Desk of Alicia Kennedy, after finding Alicia’s writing through Twitter. The essay On Work was the one that made me subscribe and I was thinking deeply about work, while coming out of the early postpartum fog after having my third child. My editing business was at a standstill and I knew I didn’t want to build it into something huge. I wanted to write, my daily life had exploded in complexity, and there was the newsletter format again – calling and electrifying. Alicia’s newsletter was also instrumental because she was the first food writer I paid attention to who wrote with a depth and breadth across the whole spectrum of cooking, politics, and culture. More than recipes (though Alicia’s are always delicious!)
Writing about food was something that I did on-again-off-again. It didn’t stick because I got bored documenting my eating or writing down the recipes I followed. I was also so young (my first attempt at a food blog was in high school) and looking out, especially in journalism school, to things that were perceived with more prestige (sports, politics, namely.) In January 2023, when I started this newsletter, it wasn’t primarily about food, although it was always there in the background.
On June 19, 2023, Alicia launched a four-week series, What Could ‘Food Is Political’ Mean?, which seemed tailor-made for the direction I was heading. The next two days I labored and birthed my fourth and last child, and spent the next month feeding my newborn daughter and reading Cuisine & Empire: Cooking in World History by Rachel Laudan, Sweetness and Power: The Place of Sugar in Modern History by Sidney Mintz, and Gastronativism: Food, Identity, Politics by Fabio Parasecoli. On August 4, I published my first essay that reflected the shift I wanted to make in my newsletter and writing as a whole: Death is Part of the U.S. Agrarian Utopia.
Josh Ozersky wrote in his essay, Consider the Food Writer, “Write anything you want on your blog or your Tumblr; nobody will hear of you, and you won’t see a penny, until some important person in the magazine world knows your name. That’s the sad secret of writing for the web, in food as in so many other fields.” This is true and false, and the truth is good and bad. I wrote in complete obscurity for many years, and from where I am now am grateful I didn’t fully commit to some of those paths. I’ll think to myself, Thank God I didn’t go all in on food blogging that was based on recipe development – that sounds like hell. And there are so many writers who should be more widely read who aren’t, which is one of the reasons I won’t quit social media. As hellish as the internet can be, it’s where I find writers who don’t have a book deal (or do have a following and are generous with their knowledge) and whose voices ring through as they consider everything and anything – like the oyster, for example.
The Good Enough Weekly comes out on Fridays, alternating essays, interviews, and shorter updates. I also take on freelance editing and writing projects. Reach out if you’re looking for an editor.
❤️❤️❤️ excited to be here!!!