BEST OF BLOOM: Sari Botton on Oldster, Aging, and Crooked Career Paths

Periodically, we revisit some of the “best of” Bloom from previous years. Bloom published this Q&A with Sari Botton on February 15, 2022, four months before we featured an excerpt of Botton’s memoir And You May Find Yourself … Confessions of a Late-Blooming Gen-X Weirdo.

Lisa Peet caught up with Botton to talk about—as Botton describes it in Oldster Magazine—“what it means to travel through time in a human body”.

by Lisa Peet

Like so many in these pandemic years, I’ve subscribed to a great pile of newsletters, loading my inbox with dispatches from creative, thoughtful, and interested writers. Perhaps my favorite is Sari Botton’s Oldster Magazine, a Substack newsletter that considers, from multiple angles, what it means to get older. She talks to people from all walks of life, of all ages—you’re never too young to think about aging. As Botton notes at the head of the newsletter, “From the time I was 10, I’ve been obsessed with what it means to grow older. I’m curious about what it means to others.”

Those others include writers, artists, designers, editors, musicians, athletes, retirees, and folks who fall into none of those buckets. Some write personal essays exploring the ways age has complicated—or simplified—their relationships to work, or sexuality, or beauty routines. Others answer Botton’s wonderfully evocative Oldster Questionnaire, reflecting on their chronological age, inner age, limitations, expansions, role models, birthdays, and more. (Take it yourself, when you have a moment, and see what you turn up.)

In addition to serving as an eloquent ambassador of getting on—before Oldster, when she worked as essays editor at Longreads, she created the series Fine Lines: Writing About Age— Botton is also a writer, editor, and teacher. She compiled two anthologies that look at living in New York from both sides of the exit ramp, Never Can Say Goodbye: Writers on Their Unshakable Love for New York (Touchstone/Simon & Schuster, 2014) and Goodbye to All That: Writers on Loving & Leaving New York (Seal Press, 2013)—a reissue, with new essays reflecting the COVID-era exodus, came out in 2021. Currently she’s a contributing editor at Catapult and is at work on her own memoir, coming this summer.

Bloom caught up with Botton on an icy February weekend to find out more about the genesis of Oldster, and why thinking about aging hits a note for everyone.

Lisa Peet: Maybe it’s just that I’m getting older, but I feel like I’m seeing the experience talked about, and represented, more than it used to be. Do you think aging is having its moment? Or is it just that older people are more visible than ever?

Sari Botton: Well, I think everyone is more visible right now because of social media. It has made us see ourselves and it makes us compare ourselves to others, which can be both bad and good—we can see that other people are struggling more than we are, we can see our privilege, other people can see our privilege. We’re seeing people we didn’t see before, because only the rich white people, and the young and beautiful—not that old isn’t beautiful, but conventionally beautiful—were the only people we used to see. And now we see everyone. I think that’s good.

I also think that a generation that has been calling attention to itself for a long time is now older. Gen X is old. I’m Gen X—I’m 56. And we are not demure the way our parents’ generations were. We’re saying, “Hey, I’m going through some stuff, and I want to talk about it,” and now there are platforms where you can do that.

LP: We started Bloom 10 years ago, partially reaction to the whole 30 Under 30 phenomenon, and now some of those folks are 40, or pushing 40. Do you see a shift happening in the online attitude about aging as people who were younger in the early days of blogging and social media hit those age milestones?

SB: I think that’s a natural thing that happens all the time. As people get older, they realize their past views of older people are really not consistent with reality. It’s one of the reasons that I started Oldster, because I feel like everyone is an oldster to someone younger than them and a youngster to people older than them. A lot of it is about this realization of what age is.

I also think that we’re interrogating aging and age in a way that we never did before. I think that the Baby Boomers and Gen X have each rewritten the rules about aging so that we are stopping to think, Okay, does it still mean the same thing? You look at shows from the ‘70s and a woman who’s 60 is a little old lady with a bun, and now you’ve got Patti Smith at 74 rocking the house. So I think the paradigms have shifted, and now feels like the right time to reflect on what’s happening with age. Something’s changing, let’s get it down and look at it.

LP: You say that you were always obsessed with what it means to grow older. What did that look like before you started Fine Lines and Oldster—what forms did that obsession take, and how has that changed since you actually started digging into it?

SB: When I was younger, I was more concerned with that I wasn’t doing things soon enough, that I was behind, that I was too young for things, that I was too immature for my age group. I was intent on being precocious. I wanted to be ahead. And then it all switched for me when I was 26, 27, and got divorced for the first time. I had a very belated adolescence because I hadn’t really had one.

LP: At what point did you decide that you wanted to really dig into the concept of aging as a creative project?

SB: While I was at Longreads, I let my hair go gray. I used to have these chunky blonde stripes alternating with my brown hair. And then my brown hair started to be salt-and-pepper and it just didn’t look good anymore. I basically got my head buzzed and decided to grow in my gray. And as I was going through that, I started to see myself differently and I started to notice that other people were seeing me differently. I was having this whole experience of being an older woman.

We bought a house and a 30ish woman from the power company came over to do something and she was on the phone with her boss. I was in pigtails, dressed like I’m in junior high, because that’s how I dress. And she described me on the phone as an older woman. I was like, Oh my God—what, me? That’s when I decided to start the Fine Lines series at Longreads, because I wanted to hear what other people’s experiences were of aging, and how they understood themselves, and how they experienced the world, and what the world reflected back to them.

After I left Longreads, I realized I was not anywhere near done with the subject—I might never be—and that I would like to at some point do an anthology, but I wasn’t ready to start with a book proposal. I also was not really sure what it was going to be, so I thought, let me start a newsletter and invite people to try different kinds of things, and then I can decide.

LP: What do you feel has made Oldster possible so far?

SB: I think there’s a storytelling revolution still in play that started with social media and things like The Moth and This American Life, storytelling podcasts. I think of Oldster as my Humans of New York. People want to know what other people’s lives are like, and they want to know that other people are having similar experiences to them. Social media has facilitated it—it’s made it possible for us all to glimpse other people’s lives in various ways, and we like it, especially isolated in a pandemic.

What’s more, a lot of people have lost faith in legacy media. They want something that doesn’t come from the places they’ve been looking all their lives—they want something that feels a little special, a little niche, a little more authentic and off the beaten path.

LP: With all the folks who have answered the questionnaire, have any patterns emerged that particularly interested you, or were not what you expected?

SB: I’m really heartened to learn that I’m not the only person who feels many different ages inside myself. The second question on the questionnaire is: Is there another age that you associate with yourself? And everyone has that, everyone thinks of themselves as being a different age. I thought that was some weird thing that I did, so that’s been really heartening to me. One of the things I love about writing, about essays, about personal narrative, is that whether you’re the reader or the writer, you learn that other people are like you. That’s been really good for me, because everywhere I’ve gone in my life I felt like a weirdo and a misfit. Oldster has been a place where I’ve discovered that many people feel similarly to me, in a lot of ways, about getting older.

LP: Do you feel like people our age, especially those of us who’ve chosen creative careers, have taken a more crooked path than previous generations?

SB: I know I have—I have made a lot of weird choices. I can’t speak for other people. But there’s no blueprint, there’s no clear map for us. It’s all required a certain amount of agility, flexibility, and creativity in trying to forge a path.

LP: I have a conflict between how much more skilled I am at what I do now than I was in my 20s and 30s, and how much less time and energy I have, and how much less agility to move around in my field. And I feel like Oldster gets at that.

SB: I think that is one of the things that people are looking at—their relationship to work as they get older, and their abilities. I don’t think there’s been one clear answer. Some people feel like they’re doing better than ever before, and other people feel like they’re challenged in ways. I know that I feel both of those things. On the one hand, my brain is not what it was. But by the same token, I feel more myself—more confident in my choices, my abilities, my instincts. It’s a real paradox. On the one hand, I’m old and affected by my age. On the other hand, I’ve been marinating in my experience, and I’m better at what I do than I ever was before.

I’m having fun. I am enjoying Oldster more than any other gig of mine. It came from my curiosity and my instincts, and that always leads me in a good direction. That’s what led me to Goodbye to All That. Every time I listen to my instincts, follow my curiosity, it leads me in a good direction where I just want to keep doing more. The subjects I’m interested in, I’m really interested in. This is one of them, and I hope I hope I can keep doing it. Hey, I’m going to keep getting older, and I’m going to keep having new experiences of being older, and I’m going to keep wondering what it means for everybody else—and hopefully everybody else is too.

[Ed. note: You can subscribe to Oldster and help support another thoughtful take on getting older—which is, after all, an ongoing process we all share.]