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, of all ages, and so I invite them to take “The Oldster Magazine Questionnaire.” (*The Oldster Magazine Questionnaire is exclusive to Oldster Magazine. ©Sari Botton)
Here, Jason Diamond —author most recently of the novel Kaplan’s Plot, out last week from Flatiron Books—responds. -Sari Botton
This is a bonus questionnaire for this week, one that resulted from a Substack Live interview.
PS If you’re enjoying the work I do here at Oldster, please consider supporting it by becoming a paid subscriber. 🙏
P.S. A reminder that in my book, everyone who is alive and aging is considered an Oldster, and that every contributor to this magazine is the oldest they have ever been, which is interesting new territory for them—and interesting to me, the 59-year-old who publishes Oldster. Also, I’m trying to foster intergenerational conversations in which elders learn what it’s like to be younger, and younger people learn from elders what it’s like to be older.
When you see a piece featuring someone younger than you, try to remember when you were that age and how monumental it felt. Bring some curiosity to reading about how the person being featured is experiencing that age. Or, if you prefer, wait for the next piece featuring someone in your age group. In the last few weeks alone, I published pieces by several people in their 60s, 70s, and 80s. Not every piece will speak to every reader. I’m doing my best to cover a lot of ground and be inclusive. Please work with me! Thank you. 🙏 - Sari Botton
Jason Diamond is a writer. He lives in Brooklyn with his wife and daughter. He’s written for many outlets including the New Yorker, New York Times, Esquire, The Paris Review, and many others. His debut novel, Kaplan’s Plot, is out now from Flatiron.
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How old are you?
45.
Is there another age you associate with yourself in your mind? If so, what is it? And why, do you think?
I’ve always thought of myself as a 50-something. I sort of raised myself and while I wasn’t exactly the most responsible young person, I think that experience made me feel like I had to grow up a lot quicker.
Do you feel old for your age? Young for your age? Just right? Are you in step with your peers?
I still feel older, but I think part of that is I was born in 1980 and it’s such a weird year to have been born in because I came in when Carter was still president but came of age in Reagan’s America. I’m not a millennial, but I also feel like Gen. Xers are like my older siblings.
What do you like about being your age?
I made mistakes and I’d like to think I learned from them. I’ve got a lot of experience. I’m still curious and excited, and I think people gravitate towards older folks who try to embrace things.
I’ve always thought of myself as a 50-something. I sort of raised myself and while I wasn’t exactly the most responsible young person, I think that experience made me feel like I had to grow up a lot quicker.
What is difficult about being your age?
Not much, honestly. Though, I will say that becoming a first-time parent in your mid-40s really requires a lot of stretching and also trying to conserve energy.
What is surprising about being your age, or different from what you expected, based on what you were told?
I actually feel like an adult now. It’s a weird thing to say, especially given what I said about raising myself and feeling older than I am, but I think because I was always playing catch-up with people my age that I constantly felt immature around other people.
What has aging given you? Taken away from you?
Insight. Compassion. I’ve also been able to have conversations with the younger me and tell him he didn’t do anything wrong, and that’s been beautiful.
How has getting older affected your sense of yourself, or your identity?
I’ve started to understand that people actually pay attention to me and my work, and instead of feeling pressure from that, it has made me want to not only do better work, but try to always set a good example of how you can be a decent person making art in a world that isn’t always so decent and not so hospitable to artists.
What are some age-related milestones you are looking forward to? Or ones you “missed,” and might try to reach later, off-schedule, according to our culture and its expectations?
My 20th wedding anniversary isn’t too far out, and I feel like my wife and I get stronger as a couple all the time. It’s a beautiful thing.
What has been your favorite age so far, and why? Would you go back to this age if you could?
Right now. Every moment. I wouldn’t trade a second of it.
I’ve started to understand that people actually pay attention to me and my work, and instead of feeling pressure from that, it has made me want to not only do better work, but try to always set a good example of how you can be a decent person making art in a world that isn’t always so decent and not so hospitable to artists.
Is there someone who is older than you, who makes growing older inspiring to you? Who is your aging idol and why?
I think there are too many people to name since I’ve always appreciated folks that are older than me. Ina Garten, Larry David, Marty Scorsese, Spike Lee, Kim Gordon, Mel Brooks, and Fran Lebowitz come to mind because they’re all at least 20 years older than me, and still seem excited to work. Well, Fran doesn’t seem excited, but you know what I mean.
Also, two that always stuck with me who are no longer with us: Leonard Cohen and the ballplayer Buck O’Neil. I loved watching them in their older years.

What aging-related adjustments have you recently made, style-wise, beauty-wise, health-wise?
Not much. I’ve actually been pretty good at moisturizing and wearing sunscreen for about 15 years. I thank my wife for that.
What’s an aging-related adjustment you refuse to make, and why?
This probably isn’t the right answer, but I’ve been pretty conscious of trying to not fall into the sort of middle-aged man tropes I grew up hearing about. I don’t think I will because I’m pretty happy and fulfilled, and also constantly excited to wake up all the time.
What turn of events had the biggest impact on your life? What took your life in a different direction, for better or worse?
When my daughter was born last year. Nothing will come close to that.
I’ve been pretty conscious of trying to not fall into the sort of middle-aged man tropes I grew up hearing about. I don’t think I will because I’m pretty happy and fulfilled, and also constantly excited to wake up all the time.
What is your number one regret in life? If you could do it all over again, what is the biggest thing you’d do differently?
I don’t have any. I know it’s easy to say that, but I’ve really found peace with anything that has lingered, and for any relationships I’ve damaged, I’ve tried to reach out and patch things up.
What is high up on your “bucket list?” What do you hope to achieve, attain, or plain enjoy before you die?
I really don’t think about things like that. Whatever will happen will happen. But I will say I’ve gotten better at being able to truly enjoy things, and I’d love to keep pushing that.
Is there a piece of advice you were given, that you live by? If so, what was it, and who offered it to you?
“Don’t be a jerk.” – My grandpa. I really do try to follow that advice because he was very much not a jerk.
What are your plans for your body when you’re done using it? Burial? Cremation? Body Farm? Other?
When I was a kid I was obsessed with being mummified. Not sure we’re going that route. I do like the natural burial thing. I think there’s something beautiful about that.
Oddly, after literal decades worrying about death and obsessing over what will happen, I’m sort of chill about it because it’s going to happen no matter what. My hope is that I get a nice long life so I can watch my daughter grow up, and try to contribute as much good as possible.
How do you feel about dying? And what do you expect to happen to your “soul” or “spirit” after you die?
Oddly, after literal decades worrying about it and obsessing over what will happen, I’m sort of chill about it because it’s going to happen no matter what. My hope is that I get a nice long life so I can watch my daughter grow up and try to contribute as much good as possible.
What’s your philosophy on celebrating birthdays as an adult? How do you celebrate yours?
I like seeing my friends on my birthday. It’s a nice reminder of the life I’ve built. My friends are my family and I love them very much.














