Heavyweight - Regrets, I've Had a Slew

Episode Date: October 15, 2026

In February, the Heavyweight team headed to Brooklyn for a live show at On Air Fest. There was a countdown of Jonathan’s most regrettable moments from the show, and an audience Q&A with producers Kalila and Stevie. And fortunately for you, we recorded it all.See omnystudio.com/listener for privacy information.

This is an I-Heart podcast. Guaranteed Human. Malcolm Gladwell here. My new book, The American Way of Killing, investigates America's gun violence crisis. Why is the richest country in the world plagued by such lethal violence? Through a series of stories, interviews, and archival tape, I confront one of today's most urgent moral dilemmas and examine why the U.S. has never quite understood its own problem

and why you can't fix what you refuse to see clearly. Get the American Way of Killing at Pushkin.fm slash audiobooks or at Audible, Spotify, or wherever audiobooks are sold. Pushkin. Back in February, I participated in a podcasting festival called On Air Fest that took place in Brooklyn, New York. Whereas I'm usually the one helping a stranger confront their deepest, most uncomfortable regrets. On this occasion, I turned the spotlight on myself, live on stage. And because we recorded the whole thing, you, dear listeners, can journey back in time

to experience my dangerously personal self-interrogation from the safety of your earbuds. And that's all coming up after the break. Okay, welcome back to the space. So after a decade of sharing other people's regrets on the acclaimed and beloved podcast heavyweight, host Jonathan Goldstein looks back on his own regrets, making the show. Revisiting

10 years' worth of stories and tape Jonathan reflects on his work and then opens it up for an audience Q&A with his producer's Kalila Holt and Stevie Lane. So please welcome Jonathan Goldstein. And so you are wondering, what are the

personal regrets of a man who traffics in the regrets of others? What might a man who receives to his inbox each day countless why didn't ties, what I should have, and why did I eat that? A man for whom other people's regrets are the mud

in which he ruts like a motherless sow. What might such a man's inner hellscape look like? Well, not to make this all about me, but since I do have a microphone and you are seated in chairs facing in my direction, I will say this. The reason I created a show like heavyweight is because of my own capacity for a regret.

As a suckling baby, I'm certain I regretted choosing my mother's left breast over the right. As a teenager, I regretted things I had not even done yet. Alcohol, drugs, unprotected sex, I looked forward to regretting the hell out of them. And now as an adult, my regrets are still many. Take today, for instance. I regret the beta blockers I swallowed before coming out here. They're making me feel like I'm talking to you from the bottom of my feel like I'm talking to you from the bottom of an oatmeal bowl.

And of course, I regret agreeing to appear at On Air Fest in the first place. During that initial meeting with its organizers, I especially regret using words like, awesome and sounds like fun. But the greatest breeding ground for my remorse has been sewn in the gray garden of the heavyweight podcast itself. Sure, I've had some good times while making heavyweight. There was my stay at an airport hotel in Burbank that served free cucumber water. And there was the time I used the recording studio after Estere Perel,

and the whole room smelled of eggnog and gardenias. But nothing else comes to mind. Mostly the experience has been dominated by Dorkin Shadenshmir, the German word for, why must everything I do be the exactly wrong thing to do? Because of this tendency towards sex, second-guessing myself, re-listening to my own work and be sheer misery. But is it not I, who knows better than anyone, that it is only by reliving, re-inhabiting, and reflagulating oneself with

the past that one can finally heal? If only I had my own Jonathan Goldstein, alas, there can only be one. But for today, my on-air fest audience, you will be my Jonathan Goldstein to bear witness as together we will listen to my top seven most regrettable moments from heavyweight. Regret number one. Seed of the Pansing It. Roused from a nap, fingers sticky with great jelly, I'm often not at all prepared before an interview. But occasionally I'm so ill-equipped, I should have my podcasting license revoked. In the clip of tape I'm about to play you, I'm phoning a 102-year-old woman with an 80-year-old

regret and allowing this to happen. Hello. Hello, is this Barbara? No, this is Deborah. How are you related to Barbara? I don't know who Barbara is. The reason she doesn't know who Barbara is is because there is no Barbara.

Oh my, I'm so sorry. For some reason, I think I thought your name was Barbara. It's okay. I've lived long enough. I could take any name. I've listened to this over and over and I still can't figure out how I came up with the name Barbara. My mother's middle name is Barbara

and my girlfriend in college was named Barbara and her mother was named Deborah, so maybe that's why. Which leads me to regret number two, not keeping focus. When teasing out a story, I want details. You spilled hot coffee on yourself? Was there sugar in the coffee?

What color was your coffee cup? Often this can elevate the storytelling, but just as often it can do the opposite. In the episode called Julia, Julia has only begun to lay out a painful memory from her private school days when I am already derailed by the details of her school uniform. That's sort of a puke green uniform with a button-down white shirt, and on Mondays we had to wear ties. We also had bloomers. I don't think I ever understood what bloomers were. It was just sort of like a balloon with holes in the bottom.

And were they ruffled? See that? While it's true, I've been cursed with a lifelong inability to distinguish between bloomers, couloats, pantalets, pantaloons, drawers, and knickerbockers, should I have chosen that moment to sort it all out? Should it have required a five-minute digression and the sight of my producer frantically giving me the rapid-up motion to finally move on? This would be the part in the podcast

where the music would swell up for a few seconds allowing you to consider the question since I have no music I'll instead give you a moment while I check my phone. Regret number three being overly eager for resolution If I've learned anything from my work in the business of forcing people to ask terrifying questions

it's that it's always best to just get it over with ask the question why did you ruin my life and get ready for a painful and often unsatisfying response? But sometimes you have to take it slow. In Heavyweight's very first episode, my 80-year-old father, Buzz,

had not spoken to his 85-year-old brother Sheldon in 40 years. In the tape, I'm about to play you, they're just settling in with some small talk. My uncle Sheldon is sharing an anecdote, a filthy, inappropriate anecdote about someone named Johnny from their old neighborhood. Listen for my artful attempt

to steer the conversation towards the touchy-feely, the pokey-wokey, so soon into their first encounter in decades. We're riding on Queens Boulevard. Johnny's in the backseat with the hood. He's got his naked ass up in the air, and he's humping with it. The funny thing is we had to stop for a light,

and there's a truck driver sitting in the cab, Up, hi. I looked out of the car. That was funny. Have you guys missed each other? You know, he asked the weirdest question. What is he abroad? No, I mean, I don't know.

It's, you know. A part of me still regrets not pile driving my 85-year-old Uncle Sheldon with enough force to set off his life-call medical alert bracelet. but instead I moved on. Regret number four. In the episode The Marshes,

I regret comparing Steve Marsh to a dog. While it's easy to be free in your thoughts while writing a script, it can sometimes be hard to live with the aftermath. And in this case, the aftermath was especially hard because Steve and I became friends. And every time we get together, somewhere in the back of my mind is my guilt

over how I described Steve in the episode. which is like this. I first met Steve Marsh at my brother-in-law's wedding. In conversation that night, Steve was given to making soulful observations, punctuated by the word man. It's perhaps also worth mentioning, though while Steve wasn't invited to the wedding, per se,

all the guests were both happy and unsurprised to see him. Of course Steve would be there, and his entrance felt like a lovable St. Bernard had just wandered into the reception hall. Would you send a wedding invitation to a St. Bernard? Of course not. But would you be darn pleased to see one show up? Absolutely.

I've always regretted comparing Steve to a St. Bernard. So I called him up to apologize. Hey. Steve? Yeah, man. What are you up to? So I'm giving this talk at On Air Fest. Yeah.

So the thing that I'm doing, I'm talking about, about my own regrets while making a show about regret. Wow. But the reason why I'm phoning is because I've always felt some amount of regret for the way that I describe you in the marshes the way that I... Really? Yeah. What part?

The Great Bernard? I always felt like maybe it was a little presumptuous to refer to you as the St. Bernard. I think I'm okay. But yeah, I don't know, man. I think you're good. I thought it was affectionate, Jonathan. It was. It sounded affectionate to me.

Okay, cool. I think my brother had so much more trepidation about it. Not the way he described him, but just like bringing up the fact that he was a meth head, you know? Oh, shit. Yeah. One regret healed and another to take its place. I guess I owe Steve's brother a call now, too.

And a great swell of music to allow some time to properly savor the irony. And regret number five. Being unable to keep from gagging. While I always feel empathy for heavyweight subjects, I don't always show it enough. In the episode Tony, Tony is regretful about the fact that while he's been made a godfather three times, he's blown it each and every time with each and every one of his three godchildren. So I decided to help him fix those blown relationships. Here's Tony trying to reconnect with goddaughter number two,

now a teenager, who he's not seen in years. We've just picked her up after school and are driving around. Knowing that young people enjoy gross stuff like poop-flavored jelly beans and Timothy Shalame's mustache, Tony takes his shot at bonding. I have a really good, disgusting story to tell you. Oh. Well, can you contextualize what disgusting means?

Oh, my God. I'm only thinking about it because it happened right around here. Oh, no, I don't like where this is going. A friend of mine, he's been collecting his vomit for the past 20 years in a gigantic tin, like a gigantic metal drama in the basement. Oh, my God. What the heck? Instead of nearly retching, I should have been more supportive,

offering Tony helpful follow-up questions to help keep the vibe light. I could have asked, did your friend buy this gigantic metal tub at the container store? And is there a special aisle for barf? And yet, on other occasions, I do worse than merely failing to support a subject, which brings me to regret number six, disrespecting the profession of journalism by abandoning even the semblance of objectivity. In the episode Joey, a young, roller-blading hipster named Joey, is living in a loft with six other young hipsters.

Since Joey is crippled by shyness, he spends all his days hiding in his room. But it isn't even really a room so much as it's an area in the living room walled off by a bedsheet. Eventually, Joey's roommates grew so upset by his creepy secret of ways that they kicked him out. Finding it hard to get a handle on Joey's essence, I decided to speak with his sister-release. She tells me about the phone call Joey made to her On the day he was ejected from the loft He was like almost in tears telling me this story

And he told me about how he cried Which is always He doesn't cry that often You could tell it was a big deal that he expressed That he cried about it And he told the whole story And I was laughing so hard Because it's a really funny story

And I wanted him to see that it was funny too and he could see the humor in it, but he was also pretty clearly devastated. When I ask Elise, what's so funny about her brother crying on the phone, she makes a pretty strong case, casually eviscerating Joey in the way only a loving sister can. Him and his rollerblades and often funny-looking tank tops, his like creeper mustache and his mullet.

And this is where I should have shown more professionalism, rather than laughing, which is what I did. Definitely just the look of him. Hang on a second. He has a mullet. Full mullet, full creepy young child mustache. And his shoulders and arms look strong, but they're small. And same with his legs.

His legs are shockingly skinny skinny. They do have an incredible shine. to them, I will admit. I've always regretted my euphorically blithe tone, so I decided to call up Joey and comp to it. Is this, Mr. Jonathan Goldstein? Joey, can I tell you why I was phoning?

Please. So I'm talking about my personal regrets while making a show about regret. Okay, a little meta. So I played a passage from our story, your story, the Joey story, a regret that I had was when I spoke with your sister

how I didn't maintain a lot of journalistic objectivity, I ended up kind of laughing with her. Okay, I'm sorry you feel that way. You've always felt okay about it, I hope? That part, yeah, no, that was... Oh, okay. You say that part, was there another part

that you felt less okay about? No. I wouldn't say that. Done and done. Apologies made, grace granted. It really is that easy. And good luck with this talk. There's a chance I'll come.

It's like down the street from my house, so I usually just sneak in. Oh, yeah. I'll leave a fire escape open for you. Would that be something you'd want to be like and he's in the audience right now kind of thing? I think if you were, yeah. I think I would do that.

Okay. And, Joey, are you in the audience? Hey, I'm so glad because I regret forgetting to leave the fire escape open, but you found your way in. Okay. Finally, regret number seven. I regret my regret. For me, no experience is complete until it's been thoroughly, vigorously regretted. But for some, regret isn't even a word in their vocation.

In the episode titled Christina, Christina confronts her foster mother, Isabel, over a decision Isabel made 30 years earlier. It was a decision that derailed Christina's life for the worst. At the end of the episode, after a long reconcilatory conversation, I brought up the notion of regret, asking Isabel, now in her 90s, if she at all regrets the decision that caused her foster daughter so much pain. This was Isabel's response. Oh, I wish I had to know more about it at the time, but I mean, I still have no regrets about it.

It's as though Isabel just doesn't understand what the word regret means. So I offer a working definition. If we were to set off in a time machine where we could return to that time and Christina were to say, you know. I know what you're saying, but frankly, I don't know what I do. You know, I really don't. It'll depend on kind of a mood I'm in. If you're in the mood that you're in right now. I really had no idea.

I could give you a lot of BS and tell you how good I would have been, but it wouldn't have been the truth. It's a decision that was made when she was younger. It wasn't the right one. But how many wrong decisions are made as we go along. Regretting something is a waste of time. You move on. Regretting something is a waste of time.

Unsentimental, but correct. For me, regretting something is a waste of time. has a mystical dimension too. It isn't just about wishing I'd done things differently. Regret is a reminder of our free choice, even if it means freely making poor choices, because even bad choices speak to life's possibility that it's not just predetermined,

that we're more than ball bearings repeating a mantra of, oh well, as we bump around in patterns set off by the Big Bang. Even though it often feels like we're so close to getting everything right, such a thing is, of course, never possible. the right way is outnumbered a million to one by all the wrong ways. Nonetheless, we tell ourselves, live and learn, maybe next time. Maybe next time everything will line up just right.

But until then, there's heavyweight wherever you get your podcast. Thank you. This is the part where Edith Piaf's, I regrett, was supposed to play me off, but we couldn't afford the right. So instead I'll just say thank you and scamper off to the couch. area for some Q&A with my producers, Kalila Holt and Stevie Lane. Thank you. And to get you started with the Q&A, Q, is it time for some advertisements?

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Search video podcasts and tap watch. Malcolm Gladwell here. My new book, The American Way of Killing, investigates America's gun violence crisis. Why is the richest country in the world plagued by such lethal violence? Through a series of stories, interviews, and archival tape, I confront one of today's most urgent moral dilemmas and examine why the U.S. has never quite understood its own problem and why you can't fix what you refuse to see clearly.

Get the American Way of Killing at pushkin.fm slash audiobooks or at Audible, Spotify, or wherever audiobooks are sold. Here they come. See Elaine. Kalila Hall. We were going to open the floor, hoping that maybe some of you might have some questions. Oh, yes. I would imagine that there's some stories that you spent a lot of time chasing down that ended up not panning out.

So I'm curious, like, if you feel like you've gotten better at telling when something's not going to have a satisfying resolution, what the farthest you ever went, and then pulled the plug on something? I feel like there's certain kinds of stories that we've learned. people are more reticent to participate in, like bully kinds of stories when it's sort of like mean girl situations like that. And then also sometimes

in the times where we do not find the thing that we're looking for, we really have to have something to say about it and that can sometimes be very challenging. Because if you don't find the parrot, then you have to be like, well, who among us has not found the quote unquote parrot? Maybe we're all parrots and something.

Yeah. Yeah. And when you ask, like, what's the farthest we've gotten? Of course, things have fallen apart. Like, we've located the person and they're dead. You know, like, that falls apart. But we usually just, like, shelf the story and keep checking in with the person. And sometimes, like, with time, something new comes up or something changes.

Anybody else? Yes, in the back. We were considering having Joey zipping around on his rollerblades with the microphone. My question is for the producers. I believe you guys have been with the show for a super long time at this point, right? How is your, how is the experience and role of producing the show

grown and changed? Are you able to work together in person or is it remotely? Well, I'll answer the remote thing because that's like an easier. Like that's just facts. Me and Steve are both in New York. Jonathan is in Minnesota. So we're doing a lot remotely.

But occasionally we're in the same place. And often, like, Jonathan and I just went on a reporting trip. So, like, sometimes when we're in the field, we're also together. But a lot of the editing is remote. How has it changed over time for us? I think we've, like, developed a shorthand. Yeah, like submarine talk. Yeah.

Abbreviated language. Yeah. And also it's, I think, the loss of my brain. I just, like, point to things. And I'm like, you know, that thing. I still remember when you called George Clooney, the gray-haired doctor from ER. But you knew what I was talking about. And I knew who you were talking about, yeah.

Yeah, see, that's teamwork. Right behind Sean Cole. Because the stories that you are looking into for these guests are so, excuse me, my voice is so hoarse. Because they're so personal and often these stories that people have been carrying for their entire lives, I would imagine that the work you do is changing some lives. Have there been any stories that you feel have changed your life, either in hearing them or the process of spending years working on them? Nah.

My life has changed all the time, I will say, in all sincerity. Like there's so many people that I admire. that have been subjects on the show. And what a special, unique person, you know, to lend themselves to this thing. And, yeah. Yeah, and I feel genuinely humbled that people are willing to share that with us

and, like, invite us in on that process. Yeah. For me, it's maybe not, like, one particular story, but a big lesson that I've taken from it is, like, when you have something in your life that you feel really terrible about, not always, but, like, most of the time you are thinking about it more than the other person.

And it's just a nice thing to remember in your own life for the things that you feel like you've done wrong, that probably the ripple effect is not as big as you maybe thought it was. And that if you feel weird about something, you can be like, hey, what was up with that? Like, you can ask people questions about stuff. I can not really answer you, but you can at least try. And you can record the whole thing secretly,

for potential broadcast. Depending on the state. She's kidding. That would be highly unethical. I'd love to ask about Jackie. I think it does something pretty special. And I would just love to hear about how it happened and how you've thought about it going forward.

Can we turn up the house? lights, Jackie? There's no way she would be ever. Well, how did it come about? It was just like a last minute thing. We had a very elaborate opening,

very conceptual, it involved me on the G train and the voice of the stand clear of the closing door voice had a friend who sounded just like that guy and he was like the voice of God and we would have a conversation at the beginning and at the end of the show. It was a whole

it was like producing a whole other And you can hear it if you sign up for Pushkin Plus. Yeah, I tell the whole story. Yeah. But then at last minute, I was like, I could just call up my friend Jackie who will just be annoyed and hang up and it'll be entertaining.

And that was it. And she... And I've been annoying her ever since. Ever since. But I've known her since we're children, you know. And the dynamics have been pretty much set. as a fellow producer sometimes it feels like you listen to the tape about a hundred times

with those particularly hard-hitting episodes I'm wondering like over the years has it gotten easier to listen to those really difficult stories or how do you deal with the emotional exhaustion that can come from that? While you're making it you mean? Yeah I feel like I mean like

we're all unwell is the answer, I guess. Kalila is right. We are all deeply unwell, but maintaining this level of emotional instability doesn't come cheap. We'll be right back after these paid messages from our sponsors.

With our emotional instability now fully paid for by our corporate sponsors, we return to the question of how the team copes with the heavy stuff. Here's Stevie. I don't know if this is good or bad, but I find that for me personally, like when I'm like making

making it and listening to it over and over and cutting it and like writing it before I've played it for anybody, like it starts to kind of lose its power and I don't hear it in that emotional way. And then it's like not until I'm playing it in an edit for other people that I feel like I really hear it that way again. I don't know if that's like a self-protective thing my brain is doing, but like I've never cried like cutting the tape,

but I will like cry in an edit sometimes. It's once that's scoring music's in there. Yeah, yeah, yeah. Yeah, I think you're right, though, Stevie, like, while you're actually cutting and writing, you're, like, so sort of hyper-focused that you don't have that. Like, I feel like I, in the interviews,

have a lot of feelings about stuff, and then when the episode is done. And in between, it's, like, I'm so sort of, like, tunnel vision on making the thing that, I don't know. That also feels, but, yeah, it feels like I'm, like, I'm, like, desensitized to people's deep feelings. It's like you're, you know,

it's like you're putting together cross-hirt puzzle a little bit. Yeah, totally. Yeah. Why do you think people agree to talk to you? Especially people who are, you know, from your initial email with them, it's clear that

maybe they have something to answer for they're maybe going to be the antagonist in the story. Why do they say yes? I wonder that all the time. I wonder that same thing, but I just think people aren't used to having people like ask them

questions and then sit there and really listen, like really listen. Yeah, I think also, not always because sometimes, yeah, people just don't remember, but like the one, me and the trip that we just took, the reporting trip, I feel like in that case and in some other cases too, like maybe the person we're going to also has unresolved feelings about it or like regrets. So in some ways, even if they did something wrong, it's like helpful. for them to have that space as well. And also, like, we,

when someone is really willing to, like, sit down and have a conversation with us like that, we don't want to cast them as just, like, a villain. You know, we, like, want to give people the chance to, like, give their perspective and say their piece, too. But also, a lot of people say no, and then those stories don't happen, so.

Yeah, the best episodes are the ones where there's, like, a reciprocity where both parties are getting something out of it. But, um, uh, there is a leap of faith, I think, because they're not, like, performer-type people. They're trusting us, so. I think it's probably mostly for Jonathan. There have been some episodes where it sounds like the subject

is sort of hesitating, confronting the person they're trying to maybe reconcile with, and there have been times where it sounds like you have to step in. You strike me as somebody who's perhaps non-confrontational, I'm wondering, what do you do to get yourself to confront them? I think I think about what it's going to feel like if I don't do it. And I don't always do it or I don't always do it so well. But I think about what it's going to feel like. And I don't want to live with that echoing through the years of having let the person down, you know.

So I usually try to, like, awkwardly work my way through it. I don't think I have a special skill set. I just think like I'm there, you know, in the, I always mispronounce this, the Deuce X Macchina machine, you know, like where I'm just descending and I'm wearing the toga and the beard. And like, I have to play that role, you know, so I do my best. Is some of it too, like the crossword puzzle thing where you're like, you're able to take the emotional part out of it because you're like, I need this for the episode. So I have to.

There's that also, yeah. I can't face you two without having actually just done it. Big fan of the show, so it's fun seeing you guys. I'm curious to hear from all of you on this, in the layoff between Spotify and Pushkin, what was that like for you guys personally? And did you think the show might not come back? I was really down, like unexpectedly.

Like, it was very difficult for me in a way that I did not anticipate. I felt like, oh, this isn't so bad. You know, I'll catch up on my reading. I'll take my son to school and stuff like that. But, like, pretty soon, I don't know if you were aware of just what a... Yeah. You were aware. I was really, like, not in good shape.

So, thank you, Pushkin. And look at him now. It was, like, a real... down, I would say, for me. I agree. I do think the, we've talked about this a little bit, but the person, like, taking the step back actually was helpful. Like, I feel like it then, once we were set up again, helped us, like, come back with, like, renewed energy and new, like, joy in doing the thing. I remember, like, one of the first, like, story meetings we started having when we were

looking back at pitches that had come in in that year. Jonathan was just like, yeah, let's do that one. Yeah, let's do that one. And Kaylee and I were like, who is this? I'm not normally like that. What's next? Book them. Mr. Optimism.

All right. Are we out of time? The clock's at zero. No, the clock said zero. Thank you. Thank you so much. Thank you. Heavyweight is produced by senior producer Kalila Holt

and supervising producer Stevie Lane. Today's live show was made possible by Sarah Brugier, Phoebe Flanagan, and Morgan Ratner. Mixing by Emma Munger with production help from Lisa Wang. We'll be back next week with a brand new episode. Malcolm Gladwell here. My new book, The American Way of Killing, investigates America's gun violence crisis.

Why is the richest country in the world plagued by such lethal violence? Through a series of stories, interviews, and archival tape, I confront one of today's most urgent moral dilemmas and examine why the U.S. has never quite understood its own problem and why you can't fix what you refuse to see clearly. Get the American Way of Killing at pushkin.fm slash audiobooks or at Audible, Spotify, or wherever audiobooks are sold.

This is an I-Heart podcast, guaranteed human.