In August 2021, Sari Botton ’87 dreamed she started a digital magazine called Oldster. After she woke up, she tweeted: “Maybe I’m onto something.” She had, after all, been obsessed with aging since age 10.

Now, Oldster magazine on Substack features columns, essays and a questionnaire that asks people to contemplate aging. She has more than 56,000 subscribers.

The Substack newsletter is part of what Botton’s husband, Brian Macaluso, playfully describes as “Sari’s media empire,” which include the newsletters “Memoir Land” and “Adventures in Journalism.”

Oldster magazine asks people to examine their relationship with the concept of aging with questionnaires Botton developed, including what age they associate with the most, what they like about their actual age and what they plan for their body when they’re done using it.

“All of my questions, everything I do comes out of my curiosity, my books, my newsletters. It all comes from what I’m curious about and what I want to know other people are thinking about,” she said over tacos in Kingston, where she eventually settled after moving upstate from New York City in 2005. The questionnaires have become so popular in the literary world that authors contact her to take the questionnaire and to promote their work.

“And it’s been really surprising, like some of the better-known people have reached out to me,” she said. The Go Go’s Kathy Valentine, writers Susan Orlean, Lucy Sante and Elizabeth Gilbert, art critic Jerry Saltz and singer Neko Case have all taken the “Oldster” questionnaire. Bestselling author Laura Lippman writes a periodic column.

Botton is also fascinated by death. “I think that we don’t talk enough about death, and it’s one of the things that people were responding a lot about in their questionnaires, about how they wished there was more room socially for us to talk about death. … I am somewhat obsessed with planning for death, and also, I’m completely avoiding it. I have not done anything, but I do think about it constantly, like, what am I going to do with my body and what am I going to do with all my stuff?”

The logo and merchandise for oldsters, who she considers any person who is aging, bear a distinct 1980s Gen X-era style, fitting a brand she embraced in her 2022 memoir, And You May Find Yourself ... Confessions of a Late-Blooming Gen-X Weirdo.

“When I started Oldster, I was just like, I know I want to do this. I don’t want to ask anybody for permission,” Botton said. “Substack is kind of a good place to do it on my own because they have the perfect combination, a winning combination of social media virality, crowdfunding and blogging. They marry those three things in a way that makes it possible to make a living. At least for me, I’m making a living. And in 2023, I paid out over $20,000 to writers, editors and illustrators for both Oldster and ‘Memoir Land.’”

Before turning to Substack, she ran the popular Kingston Writer’s Studio while pursuing her own writing, and was an editor at the nonfiction website Longreads, a job that ended during the pandemic. She freelanced for The New York Times and other publications, worked for the non-profit TMI Project, led writing workshops, taught in an MFA program and wrote her own essays.

At UAlbany, Botton majored in English and minored in journalism, studying with Bill Rainbolt, and also landed an internship with the state.

“I loved my internship at the ‘I Love New York’ campaign. It was where I wrote my first pieces of journalism, because I would write travel articles that would then get picked up by small newspapers around New York state. So, I had my first byline.” She would go on to intern with Newsday and work for Women’s Wear Daily, among other publications.

She came back to UAlbany in 2010 to teach two courses: Introduction to Reporting and News Writing and Magazine Writing for a year. In 2013, she edited Goodbye to All That: Writers on Loving and Leaving New York, a collection of essays by fellow writers, and the follow-up Never Can Say Goodbye: Writers on their Unshakable Love for New York.

In 2022, she was at a crossroads. In her memoir, she wrote: “Here we are in 2022, which finds me back in the position of juggling several low-paying gigs in order to survive. … Where do I turn next? How can I find a place for myself again? How many more times can I reinvent myself, I wonder, repackaging my experience and skills in an ever more competitive market, in a collection of dying fields?” Then Oldster took off and she finds herself working on her own terms — for herself.

Asked if she’d ever be able to go back to work for someone else, she said: “I really hope I don’t ever have to, but I’m sure I could if I had to. But I really, really like working for myself.”