Milestone roundup: Writer reflections, one year on
Takeaways from another year of publishing on Substack, and more
As we transition from winter into spring, it’s time for another selection of posts by writers reflecting on individual milestones. Writers from Investment Talk, Geneva Health Files, The New Fatherhood, Alphabet Soup, From the Desk of Alicia Kennedy and The Novelleist share insights that every Substacker could benefit from, such as developing SEO savvy and understanding how to have meaningful conversations in interviews.
Did we miss a good milestone reflection post? Share the link in the comments.
It’s been more than two years since writer Conor MacNeil left a full-time career to start his stock-market newsletter Investment Talk. In a two-year milestone reflection post, he celebrates wins such as creating and maintaining a Discord server to connect with readers, and managing subscribers. He also looks at what he wants to work on before the next milestone: subscriber churn, and honing his voice. This post, which builds off his one-year milestone post, is packed with advice.
Key takeaway: Figure out your value proposition.
Conor writes: “For Investment Talk, it’s less obvious what a reader might expect to get, or what the typical cadence of those offerings is. Thus, in 2022, I need to do a better job of letting readers know what to expect from day one.”
In January, Kevin Maguire of The New Fatherhood (TNF) clocked the first notch on his annual milestone tally. After “48 issues. Over 50,000 words. 26 editorial illustrations. Hundreds of emails, comments, and messages,” he took a moment to catalog 10 things he’d learned in writing the popular newsletter for modern dads.
Key takeaway: Surround yourself with great people, make it easy for them to get involved, and celebrate success together.
Kevin writes: “I spent 2021 learning to write. To treat it like a craft. To give it the respect it deserves,” and he has plenty to interpret on how writing TNF shaped his personal experience of becoming a parent and about modern parenting in general (it’s no secret TNF is a must-read for all parents, grandparents, and carers). Looking ahead, he says, “The guest posts also took things in directions I couldn’t have predicted, and will be a key area of focus for 2022.”
Read more: 10 things I learned from a year of TNF
Priti considers the second year of the “fairly radical act” of self-publishing, building off lessons shared from year one. She shares insights from conducting a number of reader surveys, which helped her get to know her readers better (whether diplomats, academics, policy makers, or other) and has directly informed a reshaping of her publication’s cadence and content strategy for the next year.
Key takeaway: Do less and do better.
Priti writes: “The idea is not only simply to write and report better, but to elevate the craft of writing a long read to the next level. We hope that this newsletter should not only be well-reported and well-written but also move the needle on the accountability in global health—our intended mission.
“Over a period of time, a lattice of your editorial decisions begin to emerge in your body of work. It reflects the choices we make, and the stories we write and those we do not pursue. It has been a valuable experience in making these decisions sometimes by intuition, mostly shaped by inherent news impulses, but always with the readers’ needs in mind.”
When the pop-culture late-night publication Night Water hit one year, writer Adam Cecil ran a milestone post to analyze his data, list his top posts, and detail insights drawing on his background in SEO.
He took steps to make sure posts were indexing correctly, so that “Google sees Night Water as a trustworthy source.” His milestone post includes practical advice for other writers to improve their ranking, such as seeking referrals and backlinks, and offers specific SEO advice.
Key takeaway: Teach yourself SEO.
Adam writes: “Ranking on Google is not a one-time process; it’s a long road that can take months or years to pay off, and even if you do end up ranking highly, you’re competing against the entire internet and Google’s algorithm to stay there.”
Read more: Night Water: Year One
Six months into writing Alphabet Soup—a publication sharing stories, poems, and other writings—Etgar Keret takes a look back after a 24/7 approach, saying he will use the next six months to go deeper into the foundations of his Substack and find ways to make sure he earns a living while delivering original writing.
He compares his feelings about the publication to the last Beatles concert, on the rooftop of their Apple Corps headquarters, where they escaped screaming fans to simply play and hear their voices and guitars.
Key takeaway: Get back to where you once belonged.
Etgar writes: “Alphabet Soup became my rooftop gig: my subscribers are like those passersby outside Apple, glancing at their inbox as they go about their day, only to find me shouting a story at them from the rooftop of their Gmail account. Some of them delete the newsletter, others let it sit there unread, but the few who open it are the most natural and appropriate readers I could ask for.”
Read more: Get Back – The Six Months Post
Writer and podcaster Alicia Kennedy takes the 100th podcast episode milestone on From the Desk of Alicia Kennedy as a chance to reflect on her advice for conducting a good interview. Doing interviews, she writes, has helped her “learn how to talk.” She approaches them more as “conversations” than she might in reporting, and believes in an intrinsic act of generosity on both sides. (Alicia also goes deeper on perfecting the interview in her writer advice column.)
Key takeaway: Add some rules, so as not to be too casual.
Alicia writes: “I need to lay the foundation for comfort and intimacy and not assume it, and perhaps through doing so I am also creating a base of comfort from which I can jump in with those little questions for better context without insulting the other person. I need to ask people if there are pieces they’d like me to read beforehand, topics they don’t want to discuss; I need to let them know they can draw a line at any moment. I send questions in advance, but that’s not enough. Harder still is that it’s been so long since I’ve interviewed someone in person. Virtually, it’s harder to cultivate a spark.”
One year on from starting her Substack to fictionalize her novel, The Novelleist writer (and former Substack fellow) Elle Griffin shares a post titled “I’m completely changing my newsletter strategy this year.” If that doesn’t pique your interest, she explains how a year on Substack helped her realize that people would pay for her knowledge, while her art should remain free. And by “happy accident,” she created a literary salon of fellow writers to support and champion her.
Key takeaway: Artists need communities of peers to rise together.
Elle writes: “I think having a community of peers is important for most writers—it always has been. Even Victor Hugo wrote until noon then spent the rest of the afternoon holding ‘salon hours’ for those who wished to engage him in discourse. And really that’s my whole dream for this newsletter.” About her “shoot for the moon” aspirations for 2022, she says, “My dream is to be able to write this newsletter full-time and my goal is to get there by the end of 2023. That’s two years to reach $100,000 in annual revenue and about 2,000 annual subscribers—and I’m hoping this new strategy will help me get there!”
Are you writing about a milestone in the life of your Substack publication? Send us a note about it at firstname.lastname@example.org, and we’ll consider it for a future milestone post roundup (just make sure your post is available to free subscribers). It doesn’t have to be at the one-year mark, but we’re most interested in writing that shares thoughts about what you’ve learned along the way.