Good Life Project
You Spent Years Acting Normal Inside a Life That Never Fit | Sari Botton
22 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What challenges did Sari Botton face in her midlife career?
So few of us consciously decided to suppress who we were in life. We just kind of slid into relationships, careers, and personas that looked right from the outside. And then when we looked up somewhere in our 40s or 50s or later and thought, When did I agree to this? That's what happened with today's fun and inspiring reinvention story guest, Sari Botten.
Sari built her career editing some of the most celebrated voices in American literary nonfiction. Then in her mid-50s, she was let go and watched doors close in her face, being turned down for jobs she was overqualified for, even told by interviewers in their 30s that she had, quote, done enough and it was kind of time to step aside.
Out of that experience, she launched Oldster Magazine on Substack, a publication dedicated to aging honestly at every age. It became a global phenomenon. Sari recently turned 60 and called it the best moment of her career.
In our conversation, we talk about why the most painful thing about midlife is not getting older, but realizing how long you spent performing a version of yourself that never quite fit. We talk about the Gen X inheritance, lax key kid freedom, zero parenting bandwidth, and a generation that had to figure out what normal even meant.
And we explore how sometimes an unplanned push out the door can serve as an unexpected opening to a whole new adventure and how following your instinct and taking control is so much more fun and empowering than just waiting to be chosen. And finally... why it's never too late to reinvent and reimagine, and start centering your own special flavor of weird in your work and your life.
So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project. And we'll jump right in after this short break. As we had this conversation, I believe you and I are actually the same age. Your birthday is about a month before mine, so we both turned 60 last fall.
And I've done a lot of kind of rethinking about what it means to be my age, to be in my body, my relationships, my career, my life, really, over the past few years. And I'm curious, in your mind, What is what's sort of like this the single most surprising or counterintuitive thing that you've discovered about just getting older?
The best thing I've learned, the biggest surprise has been how much possibility there is in getting older. Our culture doesn't want you to know that. Marketers want to create problems and sell you solutions. They don't want you to know that there is so much more ahead than we know. Now, yes, we're doing this in bodies that are being affected by gravity and the ravages of time.
Yes, there are things changing and hurting, but I've learned from my contributors, from commenters, that later in life, there are so many opportunities to try new things, to discover new things about yourself, to take chances at a time when you care less about other people's opinions. Yes. And it's bearing out for me. I am having the best moment of my career at 60.
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Chapter 2: How did Sari Botton launch Oldster Magazine and what was its impact?
And expect decline, expect physical decline, expect lower energy, expect to not be passionate or interested. This is where you kick back. Maybe this is where you turn around and be of service, which a lot of people do because that seems to be the thing that presents itself. But what you're describing is so counter to the narrative that's so often told to us.
You know, when you hit a certain age, it's like, okay, now's the time you pull back. And you're like, no. I'm just getting started. And it was just mind-blowing. And I've had a few other interactions, short relationships with younger men in my past, you know, in my late 30s. And...
you know, it's so counter to what women are told is going to happen to them, that we're irrelevant, that we're invisible, that we're unattractive. And throughout the piece, I have this refrain. There's an ex that lives rent-free in my head, you know, telling me in my 30s that when we get older, he's going to still be able to get young women and I'm going to be invisible.
And, you know, and then throughout the piece, I talk about this encounter with a 27-year-old who we were in a dark, you know, we were eating at the bar.
Chapter 3: What does Sari mean by 'performing a version of yourself'?
It was dark. I guess he couldn't see that I had gray hair and a wrinkly neck and a wedding band, by the way. But it was a lovely conversation. And it ended with him asking for my phone number, which was really not what I anticipated. So there's a lot about getting older that is different than what we've been told or are being told.
Yeah. I mean, where do you think that narrative comes from? Because it is pervasive.
I think it's capitalism. I really do. I think that. brands make their money by creating problems and offering us solutions to them.
Chapter 4: What insights does Sari share about the Gen X experience?
And, and so they're always trying to make us think we need more things. We need more creams. We need, I also think that we've got a youth obsessed culture. I mean, youth is pretty great. Young people are really beautiful. You know, they've got a lot of energy. But so are old people, older people, you know, I really have come to learn and believe that.
I also think sexism, patriarchy, that contributes to it. And another factor is that we didn't used to live as long as we're living now. So the narrative about what a 60-year-old is like doesn't match what
now what it did before we're living so much longer there are so many centenarians is that the word centenarians centenarians either one works for me i'm probably going to need to really learn that word because there are more and more of them and everybody wants me to give the oldster questionnaire to every one of them in their lives um but you know now that we're living so much longer i'm
What we thought a 60-year-old was like, a 70-year-old was like, is not the same as what those ages represented years ago when we were growing up.
It's so interesting you say that. I was literally just listening to a podcast last week, and there was somebody on the podcast that was – and they were kind of goofing around saying it in jest, but kind of not really also saying – I think every person should start to have to get a retest for their driver's license at the age of 60.
And this was a person who I think was probably in their early 30s. And I'm just thinking, our concept of what a human being is and is not at the age of 60 is just so wildly off right now. I'm just like, wait, what?
I know I went to a book launch a few summers ago for someone who wrote a novel about a guy in his 30s who encounters a guy in his 60s. And the guy in his 60s is portrayed as what I would think of as like someone in their 90s. And I was like six months away from 60 and I just kept cracking up and I had like I got the giggles and I was at it like, you know, in a bookstore at a book reading.
And I was like, what?
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Chapter 5: How does Sari define being 'found-ish'?
What? That's no, that's not how that is. But a person in their 30s might think that, you know, surrounds themselves.
Yeah, I certainly would have. So we kind of jumped into the deep end of the pool. For those who don't have context of who you are and what you've been up to, you self-proclaimed theater kid. You spend a lot of time in your professional life in writing and editing. And then this really interesting left turn happens about five or so years ago. Take me there.
Chapter 6: Why is it important for women to write about the mundane?
So I was an editor at a magazine called Long Reads, an online, a digital magazine. And I left thinking that I would sort of slide into another job. Like I knew of a couple that were that had just opened up that were like right up my alley that people were calling me and saying like, oh, you got to apply for that.
And then I suddenly, like, if I even got a first interview, I couldn't get a second interview. And people were saying really ageist things to me. And, you know, I was being interviewed by people in their 30s. And they were saying things to me like, haven't you done enough of this? Aren't you ready to try something else? Like, what? I'm just, like, reaching the top of my game.
What are you talking about? You know, I was 54. And one person said to me, I'm surprised a legend like you would even be interested in a job like this, which is a very backhanded way of saying you're overqualified. But also, like, you know, when you hear it from a 30-year-old, it's like, you're not complimenting me right now. You know, and then the jobs went to people in their 30s. And...
My eyes were opened. And then so many other jobs, I could not even get an interview in a field that I was kind of a star in. Everybody wanted to be published by me at Longreads. I also, I freelanced. I was a freelance editor at Catapult for a while, and everybody wanted to work with me. And yet I could not get arrested in the job market.
And then, so at Longreads, I had started a series called Fine Lines that was the precursor to Oldster. I knew I wasn't done by any means with the subject when I left at 54. I had barely scratched the surface. And I wanted to continue with it, but I also knew I needed to come up with another name. And I was stumped. I just could not come up with another name properly.
And then about 15 months after I left Longreads in August of 2021, I had a dream that I started a magazine called Oldster. And I had that dream right before I woke up. I woke up and I thought it was hilarious. I made a joke about it on Twitter, which I'm no longer on. So you can't see that tweet anymore. And then I realized, wait a minute, this is actually brilliant.
And I went right on Substack and I just launched it and it took right off. It just took off like a shot. And I've been improvising since then. And it just keeps growing. It keeps growing. I've got now 85,000 subscribers. Only a small percentage are paid. And I keep trying to let people know that, you know... That's how paid subscriptions are how, you know, how I do this.
I also pay essayists and interviewers. So more and more I'm getting people on board with that idea. You know, we were all trained from the advent of the Internet not to pay for anything because everything was paid for by, you know, advertisers and sponsors and, you know, venture capitalists. And that's not how this works anymore. So... But it's working. It's working. And it's great.
And I'm having the time of my life. I really love what I'm doing. Love what I'm learning. Love all the people I'm encountering. It's just been fantastic.
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Chapter 7: How does Sari view the societal narratives around aging?
What, in your mind, when you looked at everything else that was being written or shared, did What wasn't being said that you wanted to say? Or done that you wanted to do?
Most aging-related media is targeted at women over a certain age. And I wasn't seeing aging-related media that covered women
Chapter 8: What does it mean to live at the intersection of 'should' and 'whatever'?
not only everyone, regardless of gender, but also a wider range of people age-wise. I have been obsessed with what you're supposed to do at what age since I was 10. It wasn't like a new middle-aged curiosity for me. It was something I'd been holding on to, curious about, anxious about, obsessed with. since I was a kid who was either doing things before or after my peers.
And also, I've told this story so many times, but at my 10th birthday party, my uncle showed up and said, wow, you'll never be one digit again. And it was just like the most mind blowing piece of information. And it freaked me out. And it started this like,
obsession with what are you supposed to do when am I doing everything on time is everybody on a different path than me you know and I've lived a slightly different life like a non-conformist like I've you know I am married but I don't have children I my husband and I are both like very creative our house we describe our house as like an arts camp for two people um
And so not being on the same script as most people has been wonderful because it fits me, but I've always been anxious about, am I doing it wrong? My timeline is what I've been most anxious about. And so I didn't see other people covering this the way that I am covering this.
And so that made room for me to do it differently than everybody else and really stand out, which I think is what's happened recently.
Yeah, that makes a lot of sense to me, having followed your work for probably a couple of years now. You have this really interesting concept or sort of a question, which is – and this is related to your last book, actually, and you may find yourself a classic part of a line from Talking Heads. And the idea is what if the pain of midlife is not getting older –
But realizing how many years you spent trying to act, quote, normal inside of a life that never really fit. Take me into this.
Yeah, you know, like I talked about before, you know, there's always been this anxiety that I wasn't like other people in certain ways. And so for a lot of my young adulthood, I... I was pretending to be other people. I didn't realize it until later. I wasn't like, I'm going to now pretend I'm outdoorsy. It was like, I really just kind of, oh, there's a thing that people like.
Let me, you know, I just sort of like naturally slid into these. ideas of who I should be, and I tried to manifest them, and they always brought me to the wrong place, the wrong people. And I have wasted a lot of time being upset that I wasted a lot of time, and that's useless. I mean, it all led me here, where I feel like I belong.
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