Wild Card with Rachel Martin — Jonathan Goldstein (January 8, 2026)

Episode Overview

This episode of Wild Card features Jonathan Goldstein, critically acclaimed host of the podcast Heavyweight. Rachel Martin invites Goldstein to draw cards that prompt deep, unscripted questions about his past, beliefs, insecurities, regrets, and hopes. The conversation is personal, funny, and philosophical, exploring the quest for closure, the mysteries of change, the meaning of place, and the enduring search for connection and purpose.

Key Topics & Insights

1. Can People Really Change?

Timestamps: 00:15, 38:02, 40:20

• Goldstein opens immediately by grappling with the question of change.
  • “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, we're able to change.” (Jonathan Goldstein, 00:21 & 38:05)
• He tells the story of a 102-year-old woman from an upcoming Heavyweight episode who, after discovering lost love letters, is transformed by processing decades-old grief.
  • “She went through a lot of changes even at that age, which is kind of like a beautiful thing to see...as long as we keep going, there's always going to be change.” (Goldstein, 40:20)

2. Places that Feel Extraordinary

Timestamps: 03:10–05:28

• Goldstein describes movie theaters, especially a mid-century Minneapolis cinema, as “ordinary places that feel extraordinary,” likening the moviegoing experience to “a time machine” and a “church.”
  • “Movie theaters are kind of like...I think Pauline Kael called them like her church...That just felt like my place in the dark. Looking up at this big screen, feeling like a baby being held by somebody.” (Goldstein, 03:10–04:25)
  • He values the presence, calm, and separation from the outside world that a dark theater provides.

3. Leaving Home & Childhood Nostalgia

Timestamps: 05:51–07:55, 08:14–12:26

• Goldstein was excited to leave his parents’ house in Montreal for a cheap neighborhood, reveling in freedom (and $1.99 breakfasts).
  • “I didn't enjoy my childhood very much and the idea of being able to make my own rules was very exciting...there was just the feeling of being free.” (Goldstein, 05:56–06:59)
• His childhood bedroom was plastered with David Bowie posters, reflecting the way kids defined themselves by "splaying their personality" on their walls.
  • “It was like your whole personality was splayed across your bedroom walls.” (Goldstein, 08:39)
• He reminisces about early writing efforts, a harsh rejection from a creative writing professor, youthful angst, and a longing to understand existential questions—and how wrestling with faith and purpose contributed to his depression.
  • “He said someone that wrote the way that I did needed a therapist more than a creative writing program, which was probably true, but was still a very heavy thing to hear at like 18.” (Goldstein, 09:14–10:04)
  • “There was something very dire and desperate about it...From a very young age, just very caught up in the big questions.” (10:32)

4. On Death, Detachment, and Worst-case Thinking

Timestamps: 12:32–14:22, 32:09–37:29

• Goldstein admits a lifelong tension between fully engaging with life and staying semi-detached as a way of bracing for death.

  • “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.” (Goldstein, 12:32)

• Rachel relates as a “worst case scenario person” who sometimes imagines her own death, but finds it oddly grounding.

  • “I just go there for a little bit. I try it on and then I come back and I'm like, everyone was okay...and then it was fine.” (Martin, 14:06)

• Goldstein reflects on moods and mortality, finding peace with dying some days and wrestling with it others, and shares vignettes from Heavyweight that illustrate how decisions and regrets are often shaped by one's state of mind.

  • “It’s crazy to think that something like that [acceptance of mortality] would be so mood dependent. Is that possible?...Sometimes it just feels okay, and sometimes it just doesn’t make sense.” (Goldstein, 32:26–32:29)
  • “I feel like I kind of got the license to think about it in that way from a story, a Heavyweight story...” (36:06)

5. Closure, Regret, and Heavyweight's Purpose

Timestamps: 16:28–21:44

• Goldstein describes Heavyweight as a mediation on helping people move past unfinished business; the journey toward "closure" is more important than the destination.
  • “There needs to be that struggle and time in order to really get someplace, and to get someplace emotionally and internal. And it’s hard to dramatize that. Sometimes you just need the gun. You need that MacGuffin.” (Goldstein, 19:19–21:19)
  • He tells the story of Scott, whose search for a family heirloom led to deeper familial reconciliation.
• The process often shifts from external objects (a lost gun, a basketball career) to deeper, emotional resolution.

6. On Validation, Laughter, and Human Connection

Timestamps: 24:59–28:12

• Goldstein takes comfort in laughter, especially the unique laugh of his old friend, Jackie, which gives him “permission” to say dumb things.

  • “A laugh…lets me feel like the person isn’t taking me too seriously. I feel dangerous when I'm being taken too seriously.” (Goldstein, 25:07–25:39)

• Despite a youthful indifference to recognition, he admits he likes knowing his work is appreciated.

  • “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...is a form of validation. And I like that.” (Goldstein, 27:02)

• Rachel and Jonathan discuss loving brief connections with strangers, the role of open or guarded facial expressions, and how Goldstein has built a job talking to strangers “in safety.”

  • “What am I afraid? What would be the worst case scenario if I did walk through the world with an open face...meeting people’s gaze and not afraid of having people approach me?” (Goldstein, 23:54)

7. Beliefs: Ghosts and the Supernatural

Timestamps: 30:03–31:59

• Goldstein “doesn’t not believe” in ghosts, recounts living in an old Victorian house with mysterious smells, and recalls how he and his wife bonded over stories about the supernatural.
  • “You feel like you're just kind of passing through, that maybe one day you'll just be a faint smell.” (30:49)
  • “One of the first long text exchanges I had with my wife was about ghosts...I thought, wow, this is a real kooky chick.” (31:51)

8. Memory Time Machine: Moments to Linger In

Timestamp: 40:52–41:55

• Asked to revisit a cherished past memory, Goldstein chooses his child's birth.
  • “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.” (Goldstein, 40:57–41:55)

Notable Quotes & Memorable Moments

• “It’s like your whole personality was splayed across your bedroom walls.” — Jonathan Goldstein (08:39)
• “If you’re not totally invested in it, it’ll make death easier…life and death are side by side on a shelf.” — Goldstein (12:32)
• “I like to feel like I’m not hurting anybody when I hear the laugh.” — Goldstein (25:15)
• “Sometimes if things wrap up too neatly and too quickly, it’s not good…Sometimes you just need the gun. You need that MacGuffin.” — Goldstein (21:19)
• “As long as we keep going, there’s always going to be change. Maybe not the change that other people want to see, but there’s going to be changes.” — Goldstein (40:20)

Timestamps for Key Segments

| Timestamp | Segment/Question | |-------------|---------------------------------------------------------------------| | 00:15 | Can people really change? | | 03:10 | An ordinary place that feels extraordinary | | 05:51 | Were you excited or intimidated to leave home? | | 08:14 | Childhood bedroom details | | 12:32 | Detachment, death, worst-case scenario thinking | | 16:28 | On Heavyweight: What do you love about making this show? | | 19:19 | MacGuffins, closure, and emotional journeys | | 24:59 | What sound puts you at ease? (Laughter) | | 26:49 | Do you rely on the validation of others? | | 30:03 | Do you believe in ghosts? | | 32:09 | Have you made peace with mortality? | | 40:52 | Memory time machine: Lingering in a moment from the past |

Takeaway

In a conversation blending comedy, vulnerability, and existential inquiry, Jonathan Goldstein shares his ambivalence about change, the comfort of nostalgia, the search for closure, and the challenges of living fully in the world. Rachel Martin brings warmth and openness, and the duo model the very kind of deep, human connection that Wild Card is built to celebrate. The episode reminds listeners that life’s big questions don’t have to be answered to be worth asking—and that even at 102, it’s possible to change.

Listen for:

• Reflections on the role of struggle and imperfection in healing and moving on
• Humor woven through heavy topics
• The unique intimacy of fleeting connections—with friends and strangers alike

Endnote
This episode is a must for fans of deep-dive conversation, storytelling, and anyone who’s wondered about life’s biggest “what ifs.”