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Milestone roundup: Reflections on writing on Substack
Writer takeaways from another year of publishing on Substack, and more
As we enter the last days of summer, it’s time for another selection of posts by writers reflecting on individual milestones. Writers and podcasters from House of Strauss, Culture Study, Fútbol with Grant Wahl, The View From Down Here, The Pragmatic Engineer, My Sweet Dumb Brain, and more offer insights that every publisher could benefit from, such as letting your readers be the boss and finding a sense of purpose in your pride.
Did we miss a good milestone reflection post? Share the link in the comments.
On the anniversary of quitting his job at The Athletic and launching his sports Substack, House of Strauss, Ethan Strauss discovers that though his post topics might differ widely, the enduring throughline is his readers. Ethan shares his findings about what works, his pricing approach for year two, and plans for travel and the podcast.
Key takeaway: The pressure of a paying audience is the best kind of audience capture.
Ethan writes: “I’m of the opinion that a paying audience keeps a good kind of pressure on the performer. People might enjoy shock value or shallow affirmation, but they can find that on social media for free. Paywall is a different game. Whatever’s back there had better be something that can’t quite be found elsewhere.
You’ve made me better than I would have been, were I just yelling into a void, and that’s before we even get into the tips and thought-provoking feedback subscribers have offered. Not only do I thank you for hiring me to do what is, in my opinion, the best job in America, but I thank you for making me better at it.”
Read more: Allow me to reintroduce myself
For author Anne Helen Petersen, the first surprising realization after two years of quitting her job to focus on writing her Substack full-time is that she achieved everything she set out to do, and more.
Anne sees the “and more” part of Culture Study as the development of her thriving community of readers, defined by their “sincerity and softness.” She describes how they inspired her and each other, formed collaborations, and created their own projects, to boot. As she looks back on the past year, she notes how her Substack has replaced other forms of media for her and considers the year ahead.
Key takeaway: A vibrant, active community might just be the thing that delights you most.
Anne writes: “I’m grateful for the ability to work at a cadence that allows me to avoid burnout, but I’m also grateful to be a part of this community myself. I didn’t realize how much I’d been missing it, or how much I needed to replace online habits that made me feel like shit with ones that felt nourishing. Earlier this year, I finally felt liberated to quit Facebook, the home of the group that helped fuel so much of my original success. I spend far less time on Twitter, and the time I do spend on Instagram is (1) looking at gardening accounts and (2) interacting with members of the community.
It’s like I’d spent years looking at a laptop screen whose brightness had been turned all the way down, and every day was a painful slog just to, like, do my job, squinting and getting a headache …. and then I realized it doesn’t have to be this way. You helped turn up the brightness on that laptop screen and made my everyday life—both on- and offline—much less of a slog and much more of a delight. I hope I’ve turned up that brightness, in some small way, for you as well.”
Read more: Two Years
Over the past 12 months, veteran sports journalist and author Grant Wahl produced 30 premium magazine stories from 15 countries and was the only English-language U.S. media member who was on-site reporting from all 14 World Cup soccer qualifiers. He reflects on a year of reporting on the beautiful game in his Substack Fútbol with Grant Wahl, including leaving and returning to a post at Sports Illustrated, and being paid by his readers. He also looks to the next year, including reporting from the men’s World Cup in Qatar and the women’s World Cup in Australia and New Zealand.
Key takeaway: Who wouldn’t want a magazine-quality story with great art and reporting you won’t see elsewhere in their inbox the morning after a match?
Grant writes: “A year ago this week, I took a deep breath, turned down writing offers from traditional publications, and started my own writing site at GrantWahl.com. Few things are as professionally scary as finding out how many people are willing to pay for your work. You just can’t hide from the verdict. But I thought the risk was worth it for a few reasons:
(1) I needed to be tied to paid subscriptions, which incentivize quality, and not advertising, which incentivizes clickbait and quantity.
(2) I’m still at the top of my game.
(3) As my own boss free from the bureaucracy of a big organization, I could be a lot more nimble and efficient. Want to report three different stories on the same trip in Spain-Moldova-France or Italy-Qatar-Spain? Go do it now!
(4) I wanted to see if old-school journalism—visit, report, write—would work on Substack. I spent 25 years at Sports Illustrated magazine, most of those when SI was still the best sports publication in history, and I was hopeful that readers would pay for the kind of stories that made the old SI print magazine great.”
Read more: GrantWahl.com Is Turning 1: Thank You!
Journalist Lucy Webster says the first year of writing her Substack, The View From Down Here, has been “brilliant, scary and exhilarating.” Unexpected opportunities include moving from a political beat to one fully focused on disability advocacy, as well as landing her agent and book deal for her upcoming memoir. She looks back on 52 weeks of leaping into the unknown, helping tell the stories of others, and finding her writing sense of purpose.
Key takeaway: Lucy takes huge pride in her work and telling the stories of others, which pays off in both her relationship with her readers and sense of purpose.
Lucy writes: “Then, of course, there’s this newsletter—my own little corner of the internet and my writing baby. When I joined Substack, I set out to see what would happen, with a vague goal to break even with 70 paying subscribers within a year. To have reached over 100 in that time is amazing, and I am so grateful to everyone who has supported me.
The View From Down Here is where we’ve really got to grips with the unseen reality of disability. Together, we’ve explored what it’s really like to have a speech impediment, what it means to live beyond conventionality, and my complex journey to disability pride. I’ve poured myself into all these pieces, and I hope they’ve provided a new and valuable perspective on disability for you.”
One year since sending the first issue of The Pragmatic Engineer, Gergely Orosz commemorates the milestone by revealing the strategy that brought the newsletter to #1 in Technology on Substack. The post includes what he’s learned and his plans for the next 12 months.
Key takeaway: Nothing beats interesting, in-depth writing about a topic that you can’t read elsewhere.
Gergely writes: “The Pragmatic Engineer newsletter gives me an excuse to talk with insiders and to research topics which are more or less taken for granted within Big Tech. Even when working at Uber, I would share some insights, but I never had time to write more than two or three articles per year on my blog. By working on the newsletter full-time, this is up to two a week!
A year on, I’m even more excited about the publication than when I started. The backlog of topics has only grown, and my network of people who are open to helping with industry insights keeps expanding. There’s so much to cover in the coming year!
The reader base is far more diverse than I expected. The ‘core’ audience I write for is software engineers and engineering managers. However, I get messages from other tech professionals: data scientists, data engineers, product managers, and managers in technology—but not software engineering—who are also avid readers. I’ve also learned recruiters and HR professionals find the newsletter is relevant for their work.”
Four years ago, Katie Hawkins-Gaar texted her friend Becca about starting a newsletter “about figuring out emotions and navigating life’s ups and downs.” A few week’s later, My Sweet Dumb Brain was born. In a celebratory post, Katie reminisces about how the newsletter got up and running, what kept her going, and the more surreal surprises along the way.
Key takeaway: Writing a newsletter can be challenging, eye-opening, and instructive. But in speaking about the things we find the hardest, we can be less alone and more supportive.
Katie writes: “Looking back at that first text message, it’s amazing how much of my initial vision for My Sweet Dumb Brain has remained intact. I felt strongly about the name, the format, and the hook. Most importantly, I felt the pull to write again. After letting go of a newsletter I created at my old job, I missed having a consistent outlet to share my thoughts with an engaged audience. And after a year-plus of living with immense grief, I knew I had a lot to say, but I wasn’t interested in posting it all on social media nor was I ready to try writing a book.
A newsletter was the answer. I’m so glad that’s where I landed.
When I started this newsletter, I didn’t dream that I’d still be writing it four years later. I certainly didn’t expect I could make money from it! But here we are. Once again, none of this would be possible without you.”
Read more: It all started with a text message
When Joshua Pressman Jacobs had two standout posts with high views in the first year of his Substack, Josh off the Press, he briefly thought writing would get easier. But one of his key lessons is “how to pivot or push through the writing malaise.”
Joshua writes: “Obviously a big factor in publicly writing is promoting it. But right now I’m going to focus more on the writing part (again) and less on the promotions part. Membership to my newsletter might not grow as quickly. But the ultimate goal is not necessarily more views, but a loyal subscriber base that progresses over time. This, of course, requires consistent writing from me.
‘The main thing is to keep the main thing the main thing.’ —Stephen Covey
Happy reading, everyone!”
Read more: My commitment to writing
Astrologist and writer Frederick Woodruff took the one-year anniversary of his Substack WOODRUFF as a jumping off point to reflect on writing and creativity.
Key takeaway: Don’t let subscriber numbers be a barrier to writing. But allow reader feedback to help you up your game, adjust your efforts and master your craft.
Frederick writes: “As social platforms collapse and websites continue to devolve into carnival-like ad-riddled no-go zones, environments like Substack will evolve into what we can consider, from this vantage point, ‘the future of the internet’s ecosystem.’
Face it, the internet isn’t going anywhere, but how it operates, how it is structured and utilized is transforming.”
Read more: Conjuring a Substack is Strange Magic
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.