Isaac Fitzgerald has lived many lives.

He grew up in a shelter among the fellow unhoused in Boston. He has been a boatman, a firefighter, an international smuggler, a television personality, and, most persistently, a writer. He works high and low, niche and broad. One day he will publish a beautifully literary essay in a high-minded magazine. The next, he is on the “Today” show, radiating his love of books to millions with his latest recommendation.

Isaac also has a delightful newsletter. It’s called “Walk It Off,” and it consists of him walking places with people and talking to them about everything. The other day, in a collaboration that may turn out to be the zenith of the newsletter age, we conducted a two-way, two-site interview.

We spent much of a day together in Manhattan. First we walked and walked, and I gave Isaac a tour of some of the places that had fueled my early imagination as an aspiring writer. And then we sat down at a restaurant, and I took my turn interviewing him.

That latter interview is below. And you can read Isaac’s interview of me on his newsletter — here.

But first: I will be doing my live chat/webinar thing today at 1 p.m. New York time, 10 a.m. Pacific time, and 6 p.m. London time. If you’re new to The Ink, they’re fun and engaging. If you haven’t yet, subscribe today to join us. Subscribers will receive login details beforehand.

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“I'm interested in being a time millionaire”: a conversation with Isaac Fitzgerald

ANAND: How did the walking thing start?

ISAAC: I think we moved to New York at a similar time…

ANAND: 2012 for me.

ISAAC: For me, it might be 2013 or ’14; it was the end of the year. I hit the ground running. I was working as the books editor at Buzzfeed. That's why I moved to New York City. 

I think I got here Thursday, November 28, and I started that job December 2. I just went, went, went. I really wanted to succeed. I was working, working, working, and what ended up happening is I barely explored New York City.

I left Buzzfeed in May of 2019, and then Covid came, and during the pandemic — just to own it — I went through a breakup. So you go from being in a pandemic living with somebody in the same place, but also being very alone, and then all of a sudden I had a lot of time on my hands. 

I came to this realization: I haven't explored New York. The one thing you can do is go outside. I just started walking what ended up being 20,000 steps a day, and I just started going all over the city. Seeing all these sites, all these places, that I had meant to enjoy when I first moved to New York but I had never actually gotten around to exploring. 

Once I realized things were going to start opening back up, I wanted to make sure that I continued to walk. It was giving me such a gratitude about life in general and this city. That's when I started realizing that if I gave myself a homework assignment — basically, what is writing except for giving ourselves homework assignments for the rest of our lives? — if I had a weekly thing that made sure that I continued this habit that I had formed, I thought I would really appreciate it. That's where it started. 

ANAND: I was looking up the phrase that titles your newsletter, “Walk It Off.” There's this debate about the phrase in the common way people use it, like when you get an injury or something — “walk it off.” Some suggest that just getting back up, walking it off, maybe getting that endorphin rush, actually heals you. Others argue that the walking it off is a distraction. “Walking it off” seems to work, in other words, because it distracts you from what's not working, as opposed to fixing it. And so it may even be dangerous. I know this is an esoteric debate, but your newsletter title got me thinking. Have you come to believe that “walking it off” works? 

ISAAC: That's a great question, and that's interesting because there are all these different meanings to it, right? It's something I have given a little bit of thought to, because one could almost argue there's a little bit of toxic masculinity in that. Your shoulder gets dislocated during a game or something…

ANAND: Just throw another ball!

ISAAC: Exactly. Just walk it off.

Funnily enough for me, starting these walks and writing about them was kind of doing the opposite, though. Because walking for me really did come out of the pandemic. And now we are all being told to rush back into normalcy. Get back to our jobs, get back to the way things were, let's go, let's go. The ads have gone from "During this time of hardship…" during the pandemic to, like, that gum commercial where everyone is making out again.

So, in a strange way, continuing to walk is refusing to go back to normal. It's keeping me in touch with the pandemic. 

ANAND: That's interesting.

ISAAC: It's not walking it off. It's walking as a way to remember.

ANAND: One of the things that strikes me about you, not knowing you well but from a distance, through the distorting window of the internet, is that you're really a big friendship guy. I don't know if that resonates with you.

ISAAC: No, it does. 

ANAND: What makes you a friendship guy, and what did the pandemic do to that?

ISAAC: I've always been that way. My parents were very involved with — were beneficiaries of and then helped out with — a thing called the Catholic Worker Movement. It's this socialist community founded by Dorothy Day, with this philosophy around communal living. I grew up in a soup kitchen called Haley House in Boston, and then we lived in this house called John Leary House, which was more permanent housing for people that were having a rough time. I truly think it goes back as far as that.

I just grew up around people. I grew up around many different types of people. Even as a small child, I loved talking to them, I loved hearing their stories, I'm sure I loved blabbing their ears off, which maybe some loved, some didn't. 

I get a scholarship and go off to boarding school from the age of 13. I've almost always — save for some very lonely rural living that I had in between — been surrounded by people. Then I moved to San Francisco, where I spent almost 10 years, and I think especially there, interacting with the queer community, the idea of “found family” just really resonated with me — choosing the people that you love and build your life with. That sometimes being actual family members, but oftentimes being people you're not related to by blood. It's just very important to me, and that really hurt during the pandemic. 

ANAND: How is the newsletter for you as a form? As someone who has communicated in every form from books to TV to Twitter to a viral news site to long-form journalism, where does the newsletter fit in for you as a way of communicating? How is it different from all of the other ways that you've communicated?

ISAAC: The way the newsletter is different, thus far in my experience, is that there is more of an intimacy that I was not expecting. I'm getting these emails back, and people are sharing their personal experiences around walking in a one-on-one way. That was a very beautiful added benefit that I was not expecting. I don't think I even knew it was a function. I think the first time it happened, I was like, Wow, hang on. How'd they get my email? Oh, right, this is how it goes out. 

ANAND: Malcolm Harris, a leftist writer, makes this point that there's something kind of sad about newsletters, that they’re walling off, effectively privatizing, discourse. A lot of your stuff is not paywalled; mine's not paywalled. But it’s this idea that a shift to an email model means someone like you, a serious writing talent, now writing for this small community instead of for the commons. Do you think there's any truth to that criticism?

ISAAC: I'm sure there is, especially with paywalled content. With “Walk It Off,” I made a promise right out of the gate that I'm going to keep the weekly walks, and also a weekly question I ask, open to everyone, never behind a paywall. But I also think about this a little differently from the critics, which is that the world doesn't need to hear what I think about everything. 

ANAND: A radical concept. 

ISAAC: Actually, I'm a little surprised at the interest. I started it as a training for myself, to make sure I was writing a weekly thing. By writing a weekly thing, I made sure I was keeping up with the walking as the world reopened.

This comes after years and years and years of working for the internet at different places where it's all about traffic and making sure that you're tapped into the discourse. With the newsletter, by contrast, I get to make a little thing, I get to put it out there. If you're interested, come check it out. If you're not, great, because there is so much going on in the world. 

I believe there are people like you, incredible commentators, who really pay attention to what's going on. You're a journalist; it's your job. For me — and maybe this is my own reaction to the pandemic in a way that I haven't yet explored in therapy — I'm really trying to make my world as small as possible right now. 

ANAND: What does that mean?

ISAAC: I'm trying to delight in very small aspects of living. Morning coffee. Just taking time. Basically, I'm interested in being a time millionaire. 

ANAND: I love that phrase. 

ISAAC: These are all very unformulated thoughts, but sometimes you write the big thing and then there are a lot of people arguing. There's a lot of conflict in the world right now, and that's human existence. Walking is this way of making my life a little quieter, and I'm very interested in that, at least for right now.

ANAND: I want to double click on the Catholic Worker days. Give me an atmospheric sense of that world of your childhood and parents. 

ISAAC: When you're a kid, you don't know that your childhood is different from most people's experiences. Basically, I grew up running around the legs of numerous houseless people living in Boston — a very diverse, eclectic group of people. 

I mean, there's a whole book about this coming out next year! My parents were married when they had me — just to different people. I like to say we had more of a family shrub than a family tree. It took them many years to get everything sorted, and they got married when I was three. A fair amount of people knew about me, but I think for a fair amount of people, there was all of a sudden a three-year-old. They didn't have a place to live, and through a person in their life, they got in touch with the Catholic Worker. 

I want to be very clear: They both went to college — I think on my father's side the first of his family to go to college. On my mother's side, I think both of her parents were farmers; they'd spent at least a little bit of time at college. They came to the Catholic Worker community with an educated background, but they had no money, and they had no place to live. They started living in the housing there, and then quickly started...volunteering is not the right word. They just joined the community. It's working and living. 

Through that, the Catholic Church gave them a lot, which of course makes what happened during the “Spotlight” era and all that much harder. My dad eventually gets a job teaching religion at a local Catholic school in Boston. 

ANAND: Connected to the Catholic Worker?

ISAAC: Yeah, it's a community, and they're basically looking out for you. My mom gets a job at the Cathedral of the Holy Cross in Boston in a pretty low-level situation and then quickly rises through the ranks because she is so whip smart. Which was kind of wild. I met Cardinal Law at a very young age. We now know that the more official side of what was going on with the Catholic Church was very fucked up, but the Catholic Workers side of it, it was very small. I don't want to say it rejected the Vatican, but the Vatican wasn’t their scene. Dorothy Day was all about, Hey, let's stick to the original things. Watch out for your neighbor; take care of the poor. 

ANAND: If god is real, let's feed people. 

ISAAC: Yeah, 100 percent. I grew up with that, and that was massively impactful on my life.

ANAND: Tell me about your forthcoming memoir, Dirtbag, Massachusetts. 

ISAAC: It's basically a memoir in essays. It starts in Boston, it starts with Cardinal Law, an examination of what that means, how all that affected my parents. And how my parents, when they had me, didn't have a house, were going through their own struggles, and they truly figured out life at the same time that I'm figuring out life, which led to a lot of difficult situations. My mom and I eventually leave Boston, just the two of us. We live out with her parents in the countryside. We're living on this farm, with a lot of conflict. My father eventually does join us. Still more conflict, but right around 12 they start getting their act together, which is when I, of course, decide that I’m going to start acting out. 

ANAND: It's your turn. 

ISAAC: Yeah, exactly. It's my turn. Then I was very lucky, in that teachers took an interest in me. I knew I should get out of my house, so at the age of 14 I got that scholarship to boarding school. 

ANAND: That was your initiative, or they wanted you to get out of the house?

ISAAC: No, that was my initiative, and some teachers' initiative. To their credit, my parents could have been assholes about it, but they weren't. They saw the vision, and then I got a job on an island when I was 16. By the age of 16, I was fully out of my house year-round. 

So the memoir is going to basically be about that childhood, and then the different ways that I worked that out throughout my twenties — because I think especially for men of my background of a certain age, therapy was not something that was ever encouraged. So that working-out included a lot of rough living.

At one point, I worked with a group called the Free Burma Rangers. We smuggled medical supplies over the Thai-Burmese border. I was involved with that group for a while — it's a very long story; you'll have to buy the book! At the time, I very much viewed it as trying to help. Now I'm an older person, and I'm able to look back and recognize the white adventurism. What did it mean that I felt like I had to go halfway around the world to help people when obviously there are people in my own community that needed help? So the book reexamines the different ways I was trying to fix the conflicts in my life, without actually addressing the real issues that I had with my parents. 

ANAND: Talk to me about the word “dirtbag.” I know you had wanted to title your book “Asshole, Massachusetts,” but they wouldn’t let you. But of course this word “dirtbag” has become one with real political significance. The dirtbag left is a defining phrase of the age. Will Menaker, one of the Chapo Trap House guys, described the demographic they catered to this way: “If you sleep on a mattress on the floor and fuck in a sleeping bag, then you just might be the dirtbag left! If you’re the only dude at a function not wearing a pocket square in a linen blazer and adulting like a boss, then you’re in the dirtbag left!” So what does the word mean to you?

ISAAC: That is all very fascinating — that all these meanings have happened. Because I was working on this book for a long time. Where that word comes from for me is, in middle school especially, I hung out with a lot of older kids. It was a lot of drugs, and it was a lot of drinking in the middle of the woods, and we would refer to ourselves as dirtbags. Almost like we loved that about ourselves, which seems like exactly what's going on now on this larger political level. 

ANAND: And what was that a love of? I think that's what gets to the political part. It seems like there's both a protest and a resistance against conditions imposed, and an embracing of and celebration of one's reality.

ISAAC: It's absolutely a working-class pride thing. That's what you're holding onto, because it's something that you can be proud of.

ANAND: When we were walking earlier but not recording, you said something to me about knowing you never want to be a father. And I wanted to ask more about that.

Now, perhaps this is just me projecting as a father, but I feel this strong "I was once like you, Isaac" vibes. And it seems to me a lot of people don’t want to be a parent until they want to be a parent.

How do you think about whether you are, in fact, in a transient moment of not wanting to be a parent or whether that feels like one of the pillars of your life?

ISAAC: Well, I understand that life is change. Life is growth, life is change. In the same way that I try to remain open to people, I am always trying to remain open to change in my life. So I do understand why many parents in my life are like, "Well, you just wait, buddy."

ANAND: We're just trying to share our misery.

ISAAC: But I want to speak to that, right? Like, it's incredibly hard; it's incredibly stressful. This country is not set up in a way to make parenthood easy. The healthcare system, all of that, right? There's got to be a better way to do all of this. But I do think it's one of life's great experiences.

But, while remaining open to change, I have believed since I was a very young child — I have known, I should say — that I was not interested in a family.

And the way I would say it now — and it's not gendered even though I'm going to use a gendered word — is there's this part of me that’s like, "The world needs uncles, too." That’s how I'm thinking about it right now.

I'm hardly the first person to come up with this, but for me, on a personal level, the pandemic made me very aware of the way I can be beneficial to the friends in my life that have children, as support.

That by not having a child — which, to be fair, in certain ways is a very selfish act on my part: it's going to allow me financial freedom; it's going to allow me the ability to move around all these different things — but the non-selfish part of it for me is that I can literally show up for people who need this help, especially in this country where healthcare and finances don't make it easy to raise a child.

To that point, last summer one of the first trips I did after the pandemic began was to help my brother with his kids. I found a boat that goes from Manhattan to Martha's Vineyard. And I knew I could talk my brother into driving down from New Hampshire, and there's another boat from Martha's Vineyard to the mainland. And they came and picked me up.

I’m not the best planner in the world. I slept on a bench that evening by the beach. I literally skateboarded/walked from Brooklyn, into Manhattan, up to the ferry, get on the top deck, change boats, get picked up by my brother, go stay with him and his family, and then I was able to watch their children for one night, so they got to have the first date that they had of that year of the pandemic.

I love children. I write children's books. I hate saying this stuff, but I'm going to say it: I'm a bestselling children's books author. I'm amazed by children. I'm not one of those people who’s like, "Oh, fuck kids." I genuinely like them, but I love the idea of being of help to so many other people in my life who already have children.

And I think not having children will probably help me keep that awe and wonderment. Because the darker part of this story, which I guess I will open up about, is while watching those two children just for one night, at one point, when my niece grabbed something from my nephew, I felt in me this great rage, this true rage. Which I know parents have to deal with all the time. For me it was so startling. And so I'm sure a lot of things in my past are tied up in all that as well.

ANAND: I think you're making an important point beyond your own particular desires, about the notion of the gender-neutral “uncle,” both narrowly and broadly. Which is that our society fetishes parenthood now specifically because parenthood has absorbed a lot of the energy that used to be distributed more widely in a community — in that proverbial village. You’re making a case for the idea that there are other roles to play for our children. And writing books for them is one.

ISAAC: Yep.

ANAND: Being their uncle is another. And when we freight the parent-child relationship with all the varied responsibilities our society has towards children, it's often too much for parents alone to hold.

ISAAC: I think that's absolutely right. And to tie it into what we were talking about before, I think this comes from the fact that I had a lot of fucking adults that gave a shit about me. And I'm very lucky about that.

The two adults in my life who were supposed to be giving a shit about me at the time had other stuff going on. Because other adults stepped up, I was able to have a life that was much different than maybe the life I would otherwise have had. And so that's probably why I feel that pull. I want to be there for someone like that mentor in high school was there for me. I want to be there for someone like those librarians who helped me get out of my living situation in middle school were.

I've been lucky enough to have adults who weren't my parents who gave a shit. And of course I want to be there for my nieces and nephews in a way, but it's also important to me to be there for my friends’ kids. I live in a house right now, and my upstairs neighbor had a baby during the pandemic. And I love to go upstairs and just watch the baby while they make food or just run an errand or do something.

And, of course, there’s the selfish side of it, which is that I also like to give the baby back.

Isaac Fitzgerald is a journalist and author. You can order his latest book, “How to be a Pirate,” here. And you can read the other half of our two-way interview here. Follow Isaac on Twitter and Instagram. This interview was edited and condensed for clarity.

Thank you for reading this interview from The Ink. If you like what we do and want more of it, consider supporting our work by subscribing to The Ink. Every single subscriber helps make this enterprise possible.

Photo: Anand Giridharadas