Jonathan Goldstein on Wild Card

Summary

Heavyweight x Wild Card: Jonathan Goldstein on Wild Card

Podcast: Heavyweight (Pushkin Industries)
Special Episode: Jonathan Goldstein on Wild Card
Date: April 9, 2026
Guest Host: Rachel Martin (of Wild Card)
Main Theme:
In this crossover episode, "Heavyweight" host Jonathan Goldstein sits in the guest chair on Rachel Martin's conversational podcast "Wild Card." Through a series of randomly drawn (but thoughtfully explored) questions, they discuss identity, regret, memory, creativity, mortality, and personal change, with Goldstein’s blend of humor and philosophical candor.

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Episode Overview

This special episode departs from the usual Heavyweight structure, with Jonathan Goldstein being interviewed by Rachel Martin on “Wild Card.” The episode investigates Jonathan’s attachment to place, memory, and change, as well as the ethos behind Heavyweight and Goldstein’s own search for meaning and connection throughout his life. Together, they probe big existential themes in Goldstein's signature style: vulnerable, funny, and deeply relatable.

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Key Discussion Points & Insights

1. On Being the Interviewee

• Jonathan expresses discomfort at being the guest rather than host, joking that it felt like “the spider had become the fly” ([00:52]).
• He’s juxtaposed alongside famous Wild Card guests (Oprah, Melinda Gates), which he finds both flattering and anxiety-inducing.

"It was a tremendous loss of control, I have to say."
— Jonathan Goldstein ([00:52])

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2. Sense of Place & Memory

• An “ordinary place that feels extraordinary”: Jonathan chooses movie theaters, describing them as places of escape and transformation.

"Movie theaters...felt like my place in the dark. Looking up at this big screen, feeling like a baby being held by somebody. You know, maybe that's a part of it."
— Jonathan Goldstein ([09:14])

• On moving out of his parents’ house, he associates freedom with details like impractical cowboy boots and milk crates full of books ([11:07]).

• His childhood bedroom: plastered with David Bowie posters, a makeshift desk, and an electric typewriter on which he wrote “junk.”

"Your whole personality was splayed across your bedroom walls...if it wasn't on your bedroom wall, then you weren't in the world properly."
— Jonathan Goldstein ([13:50])

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3. Ambition, Rejection, & Early Creativity

• Goldstein shares his early drive to write, an unsuccessful attempt to get into a creative writing program, and formative rejections.
• Humor and darkness co-exist: he wanted to be a writer, but also struggled with depression and existentialism in his youth.

"I think laughter...is a signal that I'm not hurting anybody. And I think that's a biggie."
— Jonathan Goldstein ([31:54])

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4. Faith, Doubt & Existential Stew

• Childhood quests for religious certainty led to further existential confusion and eventually, a crisis of faith and depression ([16:13]).
• Throughout, Jonathan relates how he’s always wrestled with “the big questions”—where God comes from, why we exist, and the proximity of life and death.

"If you're not totally invested in it, it'll make death easier...you’re kind of, you know, here's life and here's death, and they kind of are side by side adjacent to one another on a shelf, it'll be more of a lateral move."
— Jonathan Goldstein ([17:44])

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5. Heavyweight: The Search for Closure

• Rachel lauds Heavyweight's nine seasons and influence ([22:45]).
• Jonathan values the privilege of the work, especially post-cancellation and revival.
• The "imaginary finish line" is closure, but often, the journey is more important than the destination; objects or goals (the “MacGuffin,” as in the episode about a son reclaiming his father’s gun) are just ways to reach deeper emotional truths.

"Sometimes, like, if things wrap up too neatly and too quickly, it's not good. There needs to be that struggle and time in order to get...anywhere emotionally and internal."
— Jonathan Goldstein ([27:16])

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6. Strangers, Connection, and Guardedness

• Both Jonathan and Rachel reflect on their complex relationships with strangers, empathy, and openness.
• Jonathan recalls seeing young people “with open faces” and recognizes his own self-protective “clenched” demeanor.
• He links his facility with connecting to strangers, in part, to the safety of rules and boundaries that his role as a podcast host provides.

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7. On Validation, Laughter, and Risk

• Laughter is Jonathan’s favorite soothing sound; it signals safety and permission to be himself.
• He claims that he continued writing and creating even in the face of little external validation, but acknowledges enjoying affirmation (like laughter).

"I think I would still be doing what I'm doing regardless of whether anyone liked it. That being said, I do like to know what people are thinking."
— Jonathan Goldstein ([33:13])

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8. Ghosts & Facing Mortality

• Do you believe in ghosts? “I don’t not believe in them.” Jonathan describes living in a Victorian house rich with evocative, potentially spectral, smells ([37:47]).
• On mortality, his emotional acceptance fluctuates—some days stoic, some days fearful ([39:44]).
• Jonathan relates a Heavyweight story about regret and decision-making, noting how even huge life moments—even regret—are colored by mood and perspective.

"It's crazy to think that something like that would be so mood dependent. Is that possible?"
— Jonathan Goldstein ([39:48])

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9. Change, Growth, & Hope

• Rachel and Jonathan close with the question of whether people can change.
• Jonathan says he has to believe people can change, even if just in small ways, citing a 102-year-old woman who revisited a lost love and experienced emotional growth, even at her age.

"As long as, like, we're alive and as, you know, as long as we keep going, there's always gonna be change... Not the change that other people want to see, but there's gonna be changes."
— Jonathan Goldstein ([47:40])

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10. Time Machine Prompt: The Moment to Relive

• If he could revisit one moment, it would be the birth of his son—a day “filled with so much hope and wonderful expectation and beginning” ([48:36]).
• Levity is added with praise for the NYU hospital cafeteria.

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Notable Quotes & Memorable Moments

• On creativity and parental obstacles:
  "I guess three...the milk crate, the wall to wall posters of David Bowie."
  — Jonathan Goldstein ([13:14])

• On existential prepping:
  "If you're not totally invested in [life], it'll make death easier... When the carpet is yanked out from under you, you're going to be braced for your fall."
  — Jonathan Goldstein ([18:39])

• On closure as a moving target:
  "I got you back. And I don't care about getting the gun back, but I got you back. And it's sort of like we spent two years searching for the gun just to get us to this other place."
  — Jonathan Goldstein ([27:16])

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Timestamps for Important Segments

• Opening banter about being a guest: [00:40]–[02:28]
• First “Wild Card” question about places: [07:54]–[10:40]
• Leaving home / youthful self: [11:02]–[12:49]
• Childhood bedroom & early writing ambition: [13:15]–[15:41]
• On religion, depression, and the 'big’ questions: [15:41]–[17:44]
• Heavyweight's philosophy & impact: [22:45]–[28:01]
• Talking to strangers & emotional openness: [28:01]–[31:02]
• Validation, laughter, and social safety: [31:02]–[34:29]
• Ghosts & mortality: [37:43]–[42:12]
• Regret and change: [43:45]–[47:40]
• The moment he'd relive: [48:31]–[49:35]

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Takeaways & Tone

The episode is reflective but playful, dwelling on life's unfinished business—both in personal memory and in Goldstein’s curated audio quests for closure. Goldstein is candid and self-aware, often poking fun at his neuroses, while Rachel Martin skillfully guides him (and the audience) to the emotional core.

For new listeners:
This episode provides insight not only into Goldstein himself, but also into the spirit and meaning of “Heavyweight”—the struggle for closure, acceptance of imperfection, and the possibility of change. Longtime fans will appreciate new stories and a rare look at Goldstein on the other side of the microphone.

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Further Listening

Rachel Martin suggests her interview with Jonathan’s former boss, Ira Glass, for more storytelling wisdom and behind-the-scenes insight.

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Endnote:
To stay updated, Jonathan plugs the show’s new newsletter (patreon.com/heavyweight), promising more “fun, fun, fun” in listeners’ inboxes ([50:29]).

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Summary prepared for listeners who want the wisdom, humor, and spirit of a Heavyweight episode distilled—without missing the subtle, resonant details.

Transcript

[Jonathan Goldstein]

Pushkin.

[Kayleigh]

Hello, everyone.

[Jonathan Goldstein]

Hello.

[Rachel Martin]

Hi. Hello.

[Jonathan Goldstein]

Hi.

[Kayleigh]

Here we all are in the studio.

[Jonathan Goldstein]

Yes, indeed.

[Kayleigh]

And today we've got something a little different.

[Jonathan Goldstein]

Ooh. But, Kayleigh, I don't like different things.

[Kayleigh]

Well, Jonathan, you might just have to give it a chance. Because sometimes trying new things can be scary.

[Rachel Martin]

But rewarding.

[Kayleigh]

Yeah.

[Jonathan Goldstein]

Yeah. Okay. Well, here comes the choo choo train of listening. What do we got here?

[Kayleigh]

Recently, you were a guest on a show called Wildcard. Do you remember that?

[Jonathan Goldstein]

Of course I remember. How can I forget? I was interviewed by Rachel Martin.

[Rachel Martin]

How did it feel, Jonathan, to be in the guest seat?

[Jonathan Goldstein]

It felt. I didn't like it. It was a tremendous loss of control, I have to say. It was like the spider had become the fly or something. But, you know, here's the incredible. This is nuts. It doesn't even make sense to me. I'm just looking at their past episodes. Okay. Of Wild Card, you know who was on two weeks ago?

[Kayleigh]

Who?

[Jonathan Goldstein]

Someone that's so famous, they're known by one name.

[Rachel Martin]

Cher, Adele.

[Jonathan Goldstein]

It wasn't Cher or Adele. Someone more, actually, dare I say, maybe someone more famous.

[Rachel Martin]

Obama.

[Jonathan Goldstein]

I'm gonna say as famous as Obama. Maybe more famous.

[Grainger Announcer]

What?

[Jonathan Goldstein]

All right, I'll just tell you. Oprah, she interviewed Oprah last week. She interviewed Melinda Gates.

[Rachel Martin]

She's got more money than you.

[Jonathan Goldstein]

Oprah has more money than me. Let's see, who else has more money than me?

[Kayleigh]

I would say almost every guest is probably richer than you.

[Jonathan Goldstein]

You know, honestly. So I'm on her website right now on the Wildcard website, and I'm scrolling and I'm like. I'm looking like Melinda Gates, Oprah Winfrey, Harrison Ford. I mean, crazy. And then I saw my name and I got nervous. I thought, like, that's a mistake.

[Rachel Martin]

Do you think they had someone fall through that week?

[Jonathan Goldstein]

Well, it's funny. Okay. So I did ask her that, like, why am I on the show, basically? And I thought, you know, the answer would be something like, oh, what are you talking about? Like, of course you. You know. But she was honest. She was like, well, you know how it is. Like, sometimes you do, like a biggie, and then sometimes you just do a small one or something like that. I don't know.

[Kayleigh]

I think she was more complimentary than that.

[Jonathan Goldstein]

I don't know if she called.

[Rachel Martin]

It sounds like she just wanted to talk to you, which is really nice.

[Jonathan Goldstein]

It is, it is.

[Rachel Martin]

Who wouldn't?

[Jonathan Goldstein]

Thank you. That is very nice.

[Kayleigh]

You know, me and Stevie usually are in on, like, the. You know, we're producing the conversations you have, this is one that we got to come to just as listeners. We just heard the edited version at the end and I really enjoyed it. I felt like it covered a lot of territory beyond just the typical, like, how did you come up with the show? I felt like you guys kind of went deep in a really interesting way.

[Jonathan Goldstein]

I got an interesting text from my mother in law after she had listened to it. She said that she had never had anybody express something about life and death that she had always felt.

[Kayleigh]

Whoa. Yeah, that's cool.

[Rachel Martin]

Yeah.

[Jonathan Goldstein]

Yeah. And after I got the text, I told my wife, I said, emily, you married your mother. Congratulations. Yeah.

[Kayleigh]

So we're gonna listen to that episode.

[Rachel Martin]

I think listeners will really enjoy it.

[Kayleigh]

Yeah, we did.

[Jonathan Goldstein]

And if you don't, we'll. We'll send you a check returning your. Your. Your full purchase price.

[Kayleigh]

If you don't try, try the Oprah episode. You know, maybe you'll like that more episode. God.

[Jonathan Goldstein]

But first, a word from our sponsors.

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[Jonathan Goldstein]

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[Rachel Martin]

Just a heads up, this episode does have some strong language. Do you think people can really change?

[Jonathan Goldstein]

Oh, yes. I mean, I have to believe that. I mean, even if I Don't believe it. I have to believe that. And I think, like, that's the struggle. It's like the paradox. I mean, like, we are who we are, but I think as long as we're alive, were able to change.

[Rachel Martin]

I'm Rachel Martin, and this is Wild Card, the show where cards control the conversation. Each week, my guest answers questions about their life, questions pulled from a deck of cards. They're allowed to skip one question and to flip one back on me. My guest this week is Jonathan Goldstein.

[Jonathan Goldstein]

I was writing, and no one was buying what I was selling. I just couldn't get anywhere, and I just kept doing it because I felt compelled to do it. Like a spider spinning a web, Jonathan

[Rachel Martin]

Goldstein believes in closure, which is what his massively popular podcast, Heavyweight, is all about. Helping people move on from some kind of unfinished business in their lives. Maybe that's helping someone make amends or to say thank you to a stranger or to help a person turn a page on a traumatic experience. And yes, the word heavy is in the title, but it doesn't feel that way in large part because Jonathan is very funny, and he's also got this lightness about him. He's the kind of guide who makes it clear, no matter what happens around the next bend, he'll be there rooting you on. I am so very happy to welcome Jonathan Goldstein to Wildcard. Hi.

[Jonathan Goldstein]

Hi. Thank you so much. It would have taken me about 10 tries to get that and so much editing.

[Rachel Martin]

I don't believe you.

[Jonathan Goldstein]

But it's true. And yet it's true.

[Kayleigh]

It's true.

[Jonathan Goldstein]

Mm.

[Rachel Martin]

I'm gonna hold up three cards. You pick randomly. One, two, or three. Okay, first three cards. First three cards.

[Jonathan Goldstein]

Now one is on my left.

[Rachel Martin]

I tend to think of one being this on my right.

[Jonathan Goldstein]

Oh, yeah. Okay. That's my left.

[Rachel Martin]

Okay.

[Jonathan Goldstein]

I'm trying to make this as confusing as possible for myself. Perfect, because I'm hoping. I guess my. My subconscious wish is that you're just gon. You know what? Forget it. We're gonna do a rerun this week. Okay. Sorry. It doesn't matter. You know what? I get the impression as a child magician that you're trying to force the number two card. It's poked out a little bit more.

[Rachel Martin]

Oh, interesting.

[Jonathan Goldstein]

Yeah. Okay, now you're forcing the one and the two. I just wanna please you. I'll take the number two.

[Rachel Martin]

I'm not pushing, I promise. Although I do like this question. Okay, look, what happened there? Okay. What's an ordinary place that feels extraordinary to you because of what happened there?

[Jonathan Goldstein]

Okay. You see, it's very difficult for me to talk about places because I'm not very place aware. Oh, I live so much of my life up in my head. For many years I thought of it as like internal and then like through therapy I've begun to see it as disassociative. Possibly, I will say broadly, movie theaters are kind of like, I think Pauline Kael called them like her church. And I think that's a little bit the way that I feel about movie theaters.

[Rachel Martin]

Yeah.

[Jonathan Goldstein]

And there's one particular. I live in Minnesota, Minneapolis. And there's an old mid century theater that used to be walking distance from my house. And I would just go see anything that was playing there and always sit way, way, way back in the back row. Cause I like to take it all in.

[Rachel Martin]

By yourself?

[Jonathan Goldstein]

By myself. I like going there with people. But if I had my druthers, it was by myself. And that just felt like my place in the dark. Looking up at this big screen, feeling like a baby being held by somebody. You know, maybe that's a part of it. I don't know what was the extraordinary

[Rachel Martin]

part of that experience?

[Jonathan Goldstein]

I think this particular theater, because it's mid century, I had the experience last Christmas of going to see It's a Wonderful Life there and I found it to be a very emotional experience. Like it, it, it's just, I mean it's just a room, but it, I don't know, all of this stuff sounds very corny. I mean my father used to watch these black and white movies and refer to it as like a time machine. And it is kind of like that there is this feeling of the past kind of erasing and you're kind of existing at all times at once. Beyond that, it's probably just pretty banal. It just. Yeah, there's just something extraordinary about in this day and age being able to kind of like turn your phone off and shut out the world for a couple of hours.

[Rachel Martin]

I mean, thank God. Hold on, there's one sound on here I need to make sure goes away.

[Jonathan Goldstein]

Is it my voice? You figured out the one thing that's dragging down this podcast.

[Rachel Martin]

Okay, three more cards.

[Jonathan Goldstein]

I'll take one this time.

[Rachel Martin]

Were you intimidated or excited about leaving your parents house?

[Jonathan Goldstein]

Leaving my parents house, I have to say. And you know, and this is kind of like you just don't know what you don't know back then. But I was nothing but excited. I didn't enjoy my childhood very much and the idea of being able to make my own Rules was very exciting. And I remember when I. I hearken back to it, now that I got a kid, I think about how sad my mother was, how she was sitting on the edge of my bed and yelling at me for what she called dismantling my room for the stuff that I was taking. You know, like I. And all I was taking was these milk crates. I didn't even have like a bookshelf. It was just like I had kept my books and stuff in milk crates. And she was like very upset that I was taking them. And I remember I wore cowboy boots, which were a very impractical thing to wear in the summer when you're moving boxes. But there was something about it that felt very romantic. I had these cowboy boots that I only wore like once a year and it felt like that was an occasion.

[Rachel Martin]

Yeah, it was.

[Jonathan Goldstein]

For the cowboy boots, even though they were slippery.

[Rachel Martin]

Where were you going to? Where were you moving from and to.

[Jonathan Goldstein]

So I was living in Montreal, that's where I grew up. And I was moving to a very cheap part of town called Point St. Charles. Yeah, it was probably no more than like a half an hour car drive.

[Rachel Martin]

Yeah. But it can be a whole world away.

[Jonathan Goldstein]

Yeah, it felt great. There was a. A $5 liter of Apple wine that they sold at the corner store and there was all these like $99 breakfast places.

[Rachel Martin]

Wow. It was like 1934.

[Jonathan Goldstein]

It was. Yeah. Back. This is back in the 30s. Yeah. I could listen to all the jazz music I wanted. Yeah. No, I don't know, it was just. Yeah, it was just the feeling of. Of being free. It really. Yeah, it felt. It felt free.

[Rachel Martin]

Yeah. Last one in this round. One, two or three?

[Jonathan Goldstein]

I guess three.

[Rachel Martin]

Oh, I feel like I'm putting all these place questions to you. What details do you remember about your childhood bedroom,

[Jonathan Goldstein]

the milk crate, the wall to wall posters of David Bowie.

[iHeart Podcast Announcer]

Nice.

[Jonathan Goldstein]

Very big David Bowie fan. To this day, my father will call me up on the phone if David Bowie's on TV and he'll say, oh, your buddy's on tv. He just didn't get it.

[Rachel Martin]

No, but I love that he knows that you like him and he's like trying to connect with you.

[Jonathan Goldstein]

Yeah, yeah, just a lot of like pictures taken out of magazines and newspapers and it must still be the same way for kids, but it was like your whole personality was splayed across your bedroom walls. Like if it wasn't on your bedroom wall, then you weren't in the world properly. You know, you had to lead with all of these things on Your wall. I had this little card table that. With a type. With an electric typewriter that I wrote on.

[Rachel Martin]

What were you writing at the time?

[Jonathan Goldstein]

Oh, such junk. I remember when I applied into the creative writing program at the university in Montreal Concordia with such high hopes, because from a very young age, I was always writing and making plays and making radio plays and, you know, forcing my friends into performing in them. And I applied, put together what I thought was my best work. And I applied to this creative writing program, and the guy, the professor running the program, rejected me. And I couldn't understand why. And I made a meeting with him, and he said that someone that wrote the way that I did needed a therapist more than they needed a creative writing program. Which was probably true, but was still, like, a very heavy thing to hear at, like, 18, you know, not helpful guidance, but it was all, like, nuts. I mean, like, young men are. Or at least me and my friends, I mean, we were just nuts. We were just really pushing boundaries and, you know, loved Hunter S. Thompson and Jack Kerouac.

[Rachel Martin]

I mean, that's. There's nothing. No offense, but there's nothing extraordinary about that. That doesn't signal depression. That's just being an angstrom.

[Jonathan Goldstein]

No, I was just depressed on top of that. Oh, yeah, that was a. That was just a whole other side project, truly. Yeah. In various dark places, you know, very caught up in, like, what's it all about. I had, like, during my teen years, like, a foray into becoming religious and then kind of losing my faith and feeling that that brought on a really heavy depression.

[Rachel Martin]

Oh, that'll do it.

[Jonathan Goldstein]

I wanted to believe, and I just couldn't figure my way into it. And, yeah, just, like, very. From a very young age. Just very caught up in the big questions, I guess. And not that that's necessarily a formula for depression, but for me, I don't know, there was something very dire and desperate about it. I remember asking my father, like, at a. Like, at a very, very young age, like, where God came from. And that feeling, like a very basic question, because God was a given. But, like, okay, so then where does God come from? And I remember him telling me that I should look it up. And I had these child's encyclopedia set and looking up. What did you look up under G. Yeah, like God. And like, I thought, oh, well, I'm gonna get to the bottom of this in two seconds, obviously, everybody gonna be here. And it wasn't. I remember, like, looking at the Bible and thinking, like, oh, it must be before Genesis, like before. But you know, there's like, no preface. There's no.

[Rachel Martin]

Yeah, there's nothing there.

[Jonathan Goldstein]

It just starts with the big bang and that's it. But I don't know, it was probably also more banal. Like, I probably couldn't meet any girls, you know.

[Rachel Martin]

Yeah, that's a big existential stew of things.

[Jonathan Goldstein]

Yeah. Yeah. Very profound. Very. Yeah. Well, Schopenhauer esque. Is that a word?

[Rachel Martin]

Sure, it is now.

[Jonathan Goldstein]

Yeah.

[Kayleigh]

Yeah.

[Rachel Martin]

But I think dealing with that, the uncertainty of life at that angle, but I couldn't.

[Jonathan Goldstein]

Yeah, but I know, you know, it's still something that I struggle with. I mean, I just want to really let go and give myself over to life. But I don't know, there's always just been this feeling of, like, if you're not totally invested in it, it'll make death easier. You know, like, if you live your life as though, like, you're kind of, you know, here's life and here's death, and they kind of are side by side adjacent to one another on a shelf, it'll be more of a lateral move. Good night, folks. It's not too, it's not too late to, like, run the rerun.

[Rachel Martin]

I'm just trying to understand it. It means putting as much effort into the thinking about death as the thinking about life. And they are equal experiences. And so then it's a lateral mess.

[Jonathan Goldstein]

Yeah, if, yeah, if you're sort of, like, braced for death from a young age, you know, if you don't fully, you know, throw yourself into the whole life thing, then when the carpet is yanked out from under you, you're going to be braced for your fall.

[Rachel Martin]

No, I, I get it. I, like, do this in my own mind. I'm, I am the worst case scenario person. It is how I live my life is to prepare for the worst things. And so I, I, I practice not being around anymore. It's dark, but.

[Jonathan Goldstein]

And you don't want to model that for your.

[Rachel Martin]

I know. I have two of them. I, I, I don't think that's a great way to live, but it actually doesn't bring me down. I don't get bummed about it.

[Jonathan Goldstein]

Oh, that's wonderful.

[Rachel Martin]

Just go there for a little bit. I try it on, and then I come back and I'm like, everyone was okay. Everyone. When I was gone, in my imaginary death, everyone grieved and then they lived beautiful lives, and then it was fine.

[Jonathan Goldstein]

Oh, that's wonderful. So you're thinking about your own absence from the perspective of those you love. Yeah, I guess that's the mark of a superior human being. That's not how I was thinking about it. I was thinking more fuck all y'. All. No, no, no. I'm just kidding.

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[Jonathan Goldstein]

Oh, my goodness, he caught it.

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[Jonathan Goldstein]

Everyone wants to be here.

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[Jonathan Goldstein]

IHeartradio producer Kalila Holt.

[Rachel Martin]

Yeah.

[Jonathan Goldstein]

What do you love most about spring?

[Kayleigh]

Winter is so depressing that when you get to spring and there's just like a sense of relief, you know?

[Jonathan Goldstein]

Totally. Get lost, old man. Winter.

[Kayleigh]

Yeah. Get out of here.

[Jonathan Goldstein]

I love spring, too. I like bringing my son to the park. I like shooting baskets. But, you know, one of the unfortunate things about the spring is the bugs.

[Kayleigh]

That is very true.

[Jonathan Goldstein]

They start marching into my house. It's like they own the joint. But this spring, I'm going to enjoy the season worry free. Why? Well, because I've got Pesty. Now, it's an effective, easy and affordable way to control pests in your home all by yourself. You don't need strangers snooping around coming inside.

[Kayleigh]

You don't need strangers snooping when you've already got bugs snooping.

[Jonathan Goldstein]

Seriously, enough with the snooping. And what's also wonderful about Pesti is that they customize the treatment to the season, to the location. I've got the box right here with me. It's been customized for the Minnesota spring. Whereas other pest control companies will charge hundreds of dollars. The nice thing about Pesti is that you can get started for as little as $35 per treatment. Pesti is the bestie, so forget the restie.

[Kayleigh]

Very poetic.

[Jonathan Goldstein]

Get bugs out of your house with Pesti. Go to pesti.com heavyweight for an extra 10% off your order. That's P-E-S-T-I-E.com heavyweight for an extra 10 percent off if your finance team spends more time finding data than using it. If there's one entity here and one here and one here and one here. If scaling your business feels like starting over, you need the Intuit erp. Intuit Enterprise Suite is the AI Native ERP solution that's powerful, painless and proven. Learn [e-mail] ERP.

[Rachel Martin]

Let's talk about your show for a few minutes because it is a wonderful thing. It is a wonderful thing that you have made.

[Jonathan Goldstein]

Thank you.

[Rachel Martin]

Heavyweight Been nine years. Over nine years.

[Jonathan Goldstein]

Yeah.

[Rachel Martin]

Yeah.

[Jonathan Goldstein]

We're doing our ninth season. Yeah.

[Rachel Martin]

There was a little break. The show was canceled.

[Apple Card Announcer]

Yeah.

[Rachel Martin]

At the end of 2023. And then it found new life. And as a listener, I think this is a wonderful thing. I'm sure when it was canceled you were like, meh, maybe I'm gonna do something else, lean into my writing and you know. But, but you were given this other shot. What do you love about making this show?

[Jonathan Goldstein]

Well, the simplest is that I like having a job. I found out when the show was canceled that I wasn't very good at not having a job. I had been kind of on various deadlines. Like before this I had a show in Canada on the CBC for 11 years. It had been just kind of like 20 years of deadlines.

[Rachel Martin]

This is wiretap, right?

[Jonathan Goldstein]

Wiretap, yeah, that's right. I found not having a job difficult and being back at it has given me a renewed appreciation. But I love, I think I love it is a way for me to feel things and inter. Like live, interact with people and life in a way that for me is preferred. I guess there's a certain kind of safety about being alone in the attic studio a lot of the time and thinking things through in a way that I can't in real time. I don't feel like I'm great in real time.

[Rachel Martin]

We should just take a second and explain to people who haven't heard the show. I mean, I nodded to it a little bit in the intro, but you really are getting into very intimate parts of people's lives. You're helping them through specific regrets and longing and helping them find closure. Like someone who's, you know, did something to someone, wronged them 20, 30 years ago, more. You literally go find that person for them and, and help them sometimes come confront them and have a one on one exchange. Sometimes you don't find the person, but somehow through the journey they've been able to understand their life in a more intimate way. I mean, it's, it's very emotionally intense work. I mean, you, you say you do this work in part just to feel things. That's a lot of feelings, Jonathan. Like it's a lot of living that you're navigating through other people's experience.

[Jonathan Goldstein]

Yeah, yeah, there's definitely, like you say, closure. I think that is. Yeah, that is always kind of, like, the imaginary finish line. I don't think most of the episodes get there, but it is true what you also say about the process of getting there. And sometimes it's the thing that people are searching for is somewhat of a MacGuffin. Like, there was one episode called Scott where this former heroin addict had sold all of many prized possessions that belonged to his father, among which was this gun that his grandfather, his father's father, had taken off a Nazi in World War II. And he had sold this gun to a pawn shop to buy drugs. And he wanted to get the gun back, and he felt like he owed it to his father. And spoiler alert, he gets the gun after. I mean, I didn't think we were ever gonna find this gun again. It might have taken him a couple of years. We finally got it. He gives it to his dad, and his dad's like, thank you. You know, and it's just sort of like, Jesus Christ. Like, that's not gonna make a very satisfying end. It is the closure that we thought we wanted. But then it turns out that the conversation he ends up having with his father, the gun, is merely a passkey that allows us into this emotional space where his dad is able to talk about his feelings about his dad and that gun, which he never liked, and he had mixed feelings about his own father. And it ends up getting to this point where the dad's able to say to him, like, I don't really give a shit about the gun. I was afraid of losing you, and I'm so glad to have you back. And I don't care about getting the gun back, but I got you back. And it's sort of like we spent two years searching for the gun just to get us to this other place. So it's sort of like sometimes, like, if things wrap up too neatly and too quickly, it's not good. There needs to be that struggle and time in order to get. To really get someplace and to get someplace emotionally and internal. And it's hard to dramatize that. You know, sometimes you just need the gun. You need that MacGuffin.

[Rachel Martin]

I really love interactions with strangers. They make me very happy. They give me life. They make me feel connected and alive. And I think you might love strangers even more than I do, because it's. Your whole thing is like a random person will come into your inbox, and all of a sudden you. I imagine you fall in love a little bit with them and their plight or their.

[Jonathan Goldstein]

Yeah.

[Rachel Martin]

Struggle.

[Jonathan Goldstein]

Yeah. Yeah. It's complicated. When you said that about like loving to talk to strangers. I don't even know if this is really, if this makes sense, but it occurred to me this morning I was on a run and I saw these two kids. There's something very sweet about the two of them. They were, they were wandering, you know, wandering. They were. I was kind of like a. On a running path and they were just taking a leisurely stroll and they were coming towards me and they had such open faces. They looked like they were wearing pajama bottoms. Maybe that's just what kids do. But it had the affect of like feeling like they had just rolled out of bed and maybe they were, you know, in love and were just happy to be spending the morning together and. Or maybe they were on ecstasy. I don't know. But they just, their faces just seemed so open and. And I felt like stopping and telling them that that's a wonderful thing to see. And then I also thought about how like, if I was their age, that would be like, so creepy. Yeah. And that made me also. It makes me aware of just like how like clenched my. My face is. Like I'm just waiting to get punched in the face. And like, I'm just all like, you know, and it's my natural, like at this age, I mean, this is what my face has become. And I realized that a part of my fear is going through life with my face open, like those two kids, for fear that a weirdo like me is gonna come up to them. And so I kind of keep. I've kind of like after 50 odd years, my face has just become this closed in.

[Rachel Martin]

Don't talk to me.

[Jonathan Goldstein]

Yeah. And like, what am I afraid? What would be the worst case scenario if I did walk through the world with an open face and meeting people's gaze and not afraid of having people approach me, strangers approach me. What would be the worst case? Scen.

[Rachel Martin]

But you've developed a way, you've made a whole job for yourself where you get to meet strangers under your.

[Jonathan Goldstein]

In safety in a way, like with parameters and the context.

[Rachel Martin]

Round two insights cards.

[Jonathan Goldstein]

And I haven't even skipped or flipped.

[Rachel Martin]

No, you haven't skipped or flipped, but you're not judged either way.

[Jonathan Goldstein]

I mean, I don't know what's in there. There might be something that's so embarrassing. So that's why I've been saving them.

[Rachel Martin]

Yeah, save it.

[Jonathan Goldstein]

We've moved from the yellow cards to the blue cards, so I believe. I can only imagine that this More intense.

[Rachel Martin]

More intense. Okay. One, two, three, one. What's a sound that instantly puts you at ease. That's a person who lives in sounds,

[Jonathan Goldstein]

I think, a laugh.

[Rachel Martin]

Maybe anyone in particular, or all of them, all the laughing.

[Jonathan Goldstein]

And this is coming from someone who does not, unfortunately for me, like, have an easy laugh. Being in the business that I am in, it would be a nice signal to somebody of, like, hey, I'm enjoying you. But I think, yeah, all kinds of different laughs. It lets me feel like the person isn't taking me too seriously. I feel dangerous when I'm being taken too seriously.

[Rachel Martin]

You feel dangerous or the situation feels dangerous?

[Jonathan Goldstein]

I kind of feel like I shouldn't be taken too seriously. And I feel like my old friends don't take me that seriously. Like my friend Jackie, who opens the show, who I phone, who has a very endearing, distinct, kind of insane laugh I like hearing. Makes me feel like. It makes me feel free to say all kinds of really dumb things, you know, Because I feel like I'm not hurting anybody when I hear the laugh. Yeah, it's a signal that I'm not hurting anybody. And I think that's a biggie. I have a friend who told me a while ago, he's like, is this stupid? I go through life just always being afraid that I'm going to get yelled at. And I was like, no, I think I relate to that. You're afraid that you're going to hurt somebody, get yelled at, or. Yeah, you just want to be. You just want to feel like you're not. You're not messing anything up. And I don't know. Yeah, laugh is, like, a really nice thing.

[Rachel Martin]

Yeah. One, two or three.

[Jonathan Goldstein]

Three.

[Rachel Martin]

How much do you rely on the validation of others?

[Jonathan Goldstein]

I think in some ways, not a lot, because, you know, hearkening back to that story about trying to get into a writer's program when I was 18, for a very long time, I mean, I was writing and no one was buying what I was selling, and I was getting rejections. And I'm not talking, like, big magazines, but, like, zines and chapbooks, and no one would. I just couldn't get anywhere. And I just kept doing it because I felt compelled to do it, like a spider spinning a web. And in that sense, I think I was kind of, like, free of needing any validation. And maybe that's just the cockiness of youth or not knowing any better, but I think I still have that. I think I would still be doing what I'm doing regardless of whether anyone liked it. That being said, I do like to know what people are thinking. I think laughter. You know, getting a laugh or something is a form of validation, and I like that.

[Rachel Martin]

That sounds like just the right healthy amount of caring. Not that you need me to validate your sense of whether validation is important.

[Jonathan Goldstein]

I can't believe I'm doing something healthy.

[iHeartRadio App Announcer 2]

Your favorite artists in your library, your favorite songs in your playlist, but your favorite morning show.

[Rachel Martin]

Literally funny.

[iHeartRadio App Announcer 1]

Or your favorite team in action.

[Jonathan Goldstein]

Oh my goodness, he caught it.

[iHeartRadio App Announcer 2]

Or your live local news, traffic and

[Grainger Announcer]

weather implications from coast to coast.

[iHeartRadio App Announcer 1]

Yep, there's an app for all that, too.

[iHeartRadio App Announcer 2]

Iheartradio.

[iHeartRadio App Announcer 1]

We're not just streaming music, we're streaming moments.

[Jonathan Goldstein]

Everyone wants to be here.

[iHeartRadio App Announcer 1]

Add us to your entertainment line. Sign up now and Download the number

[iHeartRadio App Announcer 2]

one app for radio, the free iHeartradio app.

[Jonathan Goldstein]

IHeartradio if your finance team spends more time finding data than using it. If there's one entity here and one here and one here and one here. If scaling your business feels like starting over, you need the Intuit erp. Intuit Enterprise Suite is the AI native ERP solution that's powerful, painless, and proven. Learn [e-mail] ERP this message is a

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[Rachel Martin]

We're moving to round three beliefs.

[Jonathan Goldstein]

All right. Oh, the red cards, red cards.

[Rachel Martin]

One, two or three?

[Jonathan Goldstein]

I'll take one.

[Rachel Martin]

Do you believe in ghosts?

[Jonathan Goldstein]

I don't not believe in them. I don't know that I've ever seen one or experienced one. But I believe in the idea of them. We moved in a couple years ago into this turn of the century Victorian that I catch all kinds of weird smells in that I feel are kind of like ghostly remnants of people that lived here, that died here probably.

[Rachel Martin]

And do sensations like that, are they pleasant to you? Is that something you enjoy thinking about or is it disconcerting or neutral?

[Jonathan Goldstein]

Neutral, probably. Neutral, yeah. Like I'll smell cigarettes all on a sudden and I'll be like, that's so weird. There must have been a. There's something about the weather that's bringing out the smell, but it's, you know, of some long dead smoker who lived here. It feels like you're just kind of passing through, that maybe one day you'll just be a faint smell. I think it's probably more towards the positive if I had to choose to describe a feeling. Yeah, yeah. I mean, you know, if I saw someone crab walking on the ceiling, less so, but just something subtle, you know what I mean? Like a wisp or something. Right, right. Like a kind of spectral sort of, you know, Zero Mostel maybe. One of the first long text exchanges I had with my wife was about ghosts. She had finished reading a book about ghosts and I thought, wow, this is a real kooky chick.

[Rachel Martin]

Tell me more. I mean, not you tell me more. But you were like, tell me more. I'm into this kooky lady.

[Jonathan Goldstein]

I was like, yeah, bring it on. Yeah, yeah.

[Rachel Martin]

Three more cards. One, two or three?

[Jonathan Goldstein]

Two.

[Rachel Martin]

Have you made peace with mortality?

[Jonathan Goldstein]

Some days I feel like, yeah, take me, this is a good day to die. And I feel like one of these stoic guys in a spaghetti western. And then other days, no, I guess it really, it's crazy to think that something like that would be so mood dependent. Is that possible?

[Rachel Martin]

Right? It's so final.

[Jonathan Goldstein]

Sometimes it just feels okay and sometimes it just doesn't. Sometimes it just doesn't make sense. And then other times it just feels like, well, we all gotta go sometime. That's one of the things I liked about drinking was that feeling of like, of getting philosophical about that. Like I was someone, I'm not a great flier and that was when I relied the most on. You know, I would travel with the little bottles of booze in my pockets, so just feeling them there gave me a sense of security. And sometimes during turbulence, I'd pop one of those or two of those, and it just felt kind of like, yeah, you know, we all got to go sometimes.

[Rachel Martin]

Yeah. I think that planes often summon internal conversations about living and dying. I mean, for me for sure, too, as well, but.

[Jonathan Goldstein]

And sometimes it's like, sorry, go ahead. No, no, you say no, No, I was just gonna ask you. Like, it's. That's sometimes not a bad feeling. It's sort of like you feel like crying sometimes when you watch sentimental movies on a flag.

[Rachel Martin]

Oh, yeah. And the planes are my favorite place to cry. Yeah. It feels, like, safe. There's, like, strangers around, and I. That I find comforting. One of them might say something to me, and I might be open to that, or I might not. I don't know. But I. I like the idea that it could happen.

[Jonathan Goldstein]

What did they say to you?

[Rachel Martin]

Oh, just the possibility that they could say, are you okay? And then that. Look at it. Makes me emotional thinking about it. That breaks me. When.

[Kayleigh]

When.

[Rachel Martin]

When you're in a vulnerable place and a stranger extends themselves at all, it, like, makes me feel

[Jonathan Goldstein]

good.

[Rachel Martin]

But now I. I pivoted this to myself, and I didn't want to.

[Jonathan Goldstein]

No, no, no, no, no. Not at all. What do you say? What do you say if someone asks you, are you okay? Do you say, not at all, or do you say yes?

[Rachel Martin]

Oh, I'm thinking of one circumstance in

[Kayleigh]

particular,

[Rachel Martin]

and I said no, And I didn't want to talk about. I didn't want to say any more, but I really appreciated that they asked,

[Jonathan Goldstein]

did you tell them that?

[Rachel Martin]

No, but I said no, but it's okay. And that was it. And I think, am I trying too hard to sew this together? But I do think there's something about being suspended in air in. In a situation where you could die because planes don't make sense. And those being more truthful spaces because what the hell do you have to lose? So I get. I get the plane thing for sure. And I also.

[Jonathan Goldstein]

The thing that. Yeah, yeah. No, no, go ahead, Go ahead. No, no, no, please, please. No.

[Rachel Martin]

I. I was just gonna say you. You were saying at the beginning that it feels, like, dangerous to be so dependent on one's emotional state to determine whether or not one is okay with dying on a particular day, but maybe this is just me. I think that's a sign of a Healthy person who wakes up and like observes the question, you know, like, how is my life? And when you're saying, eh, today's a good day to go, what you're really saying is I have lived a good life.

[Jonathan Goldstein]

Yeah. Anyway, I don't know if this is a quick story, but I feel like I kind of got. Felt like I got the license to think about it in that way from a story, a heavyweight story. It was about this woman who was in her 40s and felt like her life had kind of gone off track because her foster mother didn't allow her to stay in stay with basketball because her grades weren't good enough. And she felt like her life would have been better if she could have pursued basketball, she would have gotten a scholarship. And so we went and found this foster mother who she hadn't spoken to in years, who is now this 94 year old woman to ask her why, why didn't she allow her to purs basketball when she saw it was her one passion and this woman was a tough old bird. Like it would have been so easy to say, oh, I'm sorry. And like she just wouldn't. And she had had a hard life herself. And I felt like it was almost like she was unclear on the concept of regret, you know what I mean? And I was trying to explain it to her and she was like, no, no, no, I know what you're saying. And I honestly don't know if I had a chance to do it over again with her or whether I would have done it differently. And I think it really depends on my mood, what mood I was in. And I was like, wow, that is something that is seldom acknowledged. It is, you know what I mean?

[Rachel Martin]

It is, but it isn't the whole ballgame, not to make that bad pun,

[Jonathan Goldstein]

but it is like, yeah, or more of it than we acknowledge, you know, just how drunk a lot of these founding fathers were when they were coming up with their laws and ideas, you know what I mean? And they echo through the years.

[Rachel Martin]

That was a journey, that question. This is the Last 1, Jonathan. 1, 2 or 3?

[Jonathan Goldstein]

3.

[Rachel Martin]

Do you think people can really change?

[Jonathan Goldstein]

Oh, yes. I mean, I have to believe that. I mean, even if I don't believe it, I have to believe that. And I think like that's the struggle is to really try to believe that. And I, I do think people are capable of change within limits. You know, it's like the paradox. I mean, like we are who we are, but I think as long as we're alive, we're Able to change. You know, I, I'm working on a story that's, that's should come out this season. It's about a woman who is 102 years old, who one day her kids, who are, you know, in their 70s, said, you know, you're getting on in age, we should probably clean up the storage room. And while they were doing that, they found this box containing 256 letters that had been sent to her by her fiance at the time when she was like 12, 20, who was in the war, this was World War II, who died in the war. And she had not opened up this box in and looked at these letters in over 80 years and had never really mourned the loss of this man and this relationship. She put it aside and she married a man named Irving, stayed married with him for 60 odd years, had three kids, and then finds his box and then finds herself at the age of 102, falling in love with this, with this long dead young man from her past. And in that process, like she, you know, a person who was very used to, and maybe that's a little generational too, is like you just pack it up and put it in a box and move on, but it sticks with you, you know what I mean? And like, you know, she, she went through a lot of changes even at that age, which is kind of like a beautiful thing to see, you know what I mean? As long as, like we're alive and as, you know, as long as we keep going, there's always gonna be change. You know, maybe not the change that other people wanna see, but there's gonna be changes.

[Rachel Martin]

We end the show the In Our Memory time machine where you go back and revisit one moment from your past. It's not a moment you would change anything about. It's just a moment you'd like to linger in a little longer.

[Jonathan Goldstein]

Oof.

[Rachel Martin]

I know there are many. You could pick anything, whatever comes to the fore.

[Jonathan Goldstein]

I mean, I guess the first thing that comes into my head is my child's birth. Yeah, I guess. My wife says that I, you know, like I was saying, I don't, I'm not an easy laugh. I don't. I wish I smiled more. But she said that like all through labor, I had such a big smile on my face, which kept her going. Just such a wonderful, wonderful day and just filled with so much hope and wonderful expectation and beginning and. Yeah, I think that. And I also really love the hospital cafeteria. It was at nyu. It was really good.

[Rachel Martin]

Jonathan Goldstein. It's been such a pleasure. You can hear Jonathan on the newest season of his amazing show, Heavyweight. Thank you so much.

[Jonathan Goldstein]

Thank you. Thank you.

[Rachel Martin]

Thanks so much for listening. If you like this episode, I think you would also dig my interview with Jonathan's former boss and host of this American Life, Ira Glass. Ira was super open and honest and way funnier than I expected. Check it out. This episode was produced by Lee Hale and edited by Dave Blanchard. It was mastered by Patrick Murray and Jimmy Keeley. Wildcard's executive producer is Yolanda Sangweni. Our theme music is by Ramtin Arablouei. You can reach out to [e-mail] we're going to shuffle the deck and be back with more next week. Talk to you then.

[Jonathan Goldstein]

Hi, it's Jonathan here again, breaking out of the straight jacket of being a guest. I just had one further announcement. We here at the show have started a free newsletter and it's a lot of fun. Kahlilah Holt, wouldn't you say?

[Kayleigh]

Yeah.

[Jonathan Goldstein]

Come on, step it up. Step it up.

[Kayleigh]

It's fun.

[Jonathan Goldstein]

I'm still not convinced.

[Kayleigh]

In these dark days, you can open up your inbox and have a little sunshine.

[Jonathan Goldstein]

That's right. As opposed to all of those phishing scams and viruses in there.

[Kayleigh]

And we will not try to take your information.

[Jonathan Goldstein]

No.

[Kayleigh]

Well, we will take your email address. I guess that's how you get the newsletter.

[Jonathan Goldstein]

Okay. Well, yes. Yes, indeed. But in return, you're gonna get fun, fun, fun till your daddy takes your Patreon newsletter away.

[Kayleigh]

No Social Security number required.

[Jonathan Goldstein]

If you get something in your inbox, the claiming to be from us, where they're telling you to trace your safety deposit box key onto some tracing paper and mail it into them. You'll know right away that it was not us.

[Kayleigh]

No, we would never do that.

[Jonathan Goldstein]

We just wouldn't do that. So sign up for our [e-mail] heavyweight if your finance team spends more time finding data than using it. If there's one entity here and one here and one here and one here. If scaling your business feels like starting over, you need the Intuit ERP. Intuit Enterprise Suite is the AI native ERP solution that's powerful, painless and proven. Learn more at intuit.com erp Somebody's gotta say it.

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