Totally Booked with Zibby Owens

Guest: Susan Orlean
Episode: JOYRIDE: A Memoir
Date: October 30, 2025
Location: Live at the Whitney

Episode Overview

This special live edition of "Totally Booked" features renowned journalist and bestselling author Susan Orlean discussing her debut memoir, JOYRIDE. Hosted by Zibby Owens, the conversation delves into the tapestry of Orlean’s professional adventures and personal life—detailing her storied career, turbulent romantic relationships, and resilience through societal upheavals. With Orlean’s signature candor and wit, the episode offers a revealing look at luck, heartbreak, starting over, disaster, and the ongoing mission of storytelling.

Key Discussion Points & Insights

1. The Role of Luck and Perspective

[01:45–04:13]

• Orlean reflects on the powerful role of luck throughout her career and life but clarifies that while she acknowledges fortunate turns, her attitude shapes her narrative:
  • “I truly feel, especially in the course of looking back over my career and quite honestly, my personal life, that there are so many junctures where something really fortunate happened. ... Some of this is attitude, because I can also say I could look back at the course of my life and look at a lot of things and think, well, that didn't work out, or that wasn't successful or that was a disappointment. But I choose to see it all through the lens of this good fortune.” (Susan Orlean, 01:56)
• Orlean mentions her first national story for The Village Voice, which “happened” to run the week the publication shifted to color printing, giving her piece extra attention—a providential career boost.

2. Writing as a Means of Making Sense

[25:56–27:15]

• Orlean reads a passage from her memoir, underlining her lifelong calling to writing:
  • “Writing is a job, but for me, it has always felt like a mission. I felt called, I really did, to describe ordinary life in a way that revealed its complexity and poetry, to show how rewarding it is to be open to and curious about the world and how much joy can be found in letting yourself be surprised... Writing was my effort to make sense of the human experience, of my experience.” (Zibby reading from Orlean, 25:56)
• Zibby notes how Orlean’s prose encourages empathy and a reexamination of seemingly ordinary stories.

3. Grappling with a Difficult Marriage and Infidelity

[04:13–07:56]

• Orlean discusses the emotional aftermath of her ex-husband confessing an affair on the night of her book party, and how such traumas don’t always yield simple choices:
  • “Anyone who's had a difficult relationship…as I wrote it, I thought another person would look at this and very correctly say, what were you doing? Why'd you stay so long? That's crazy. But when you're in it, it's not so simple.” (Susan Orlean, 04:42)
  • “When you hurt people or people hurt you, it tends to have the effect of attaching you more…sometimes it's this impulse to say, I can fix it. I can make it. I'm gonna stay and make it better.” (Susan Orlean, 06:10)
• She reflects on the complexity of attachment, and how the reaction to betrayal can be “primal”—driven by connection rather than logic.

4. Reinvention in Bhutan: A Fertility Pilgrimage and Younger Man

[07:56–14:10]

• Orlean narrates her journey to Bhutan, originating from a fertility-themed travel ad ("not necessary for you to have a baby"), which led to a whimsical and vulnerable chapter in her life:
  • “I just thought, I've gotta go on this trip. It just seems so funny that this was. You know, the proviso in the ad for the trip was that if you didn't wanna have a baby, you weren't required to get pregnant on the trip.” (Susan Orlean, 08:25)
• She embarks on a “holiday romance” with a much younger Bhutanese tour guide, reflecting with humor and honesty:
  • “I needed to make some new history for myself…I also felt like I don't want the last person that I slept with to be Peter. I want a new start in my new life as a person who isn't married to him.” (Susan Orlean, 12:43)
• Orlean describes the relationship as “insane, crazy, ridiculous but very sort of fun and full of good intention,” ultimately ending due to logistics and life moving forward.

5. Love, 9/11, and a Postponed Wedding

[15:13–20:18]

• Susan recounts her romance with her now-husband, planned marriage, and being swept up in history as the 9/11 attacks forced her to postpone her wedding:
  • “My great concern at the time was my wedding gown was ivory and my shoes were white…And this was, you know, who knew? Like, that was. I woke up that morning thinking, am I gonna be able to get my shoes dyed in time for the wedding...And that morning, I'm just idly listening to the news and heard this strange report about a plane hitting the World Trade Center.” (Susan Orlean, 15:41)
  • “I called my parents…and I said to my mom, you know, look, we're gonna postpone the wedding...And my mom said, it's bad luck to postpone a wedding. It says it in the Talmud. And I said, mom, I don't think it says that in the Talmud... But the feeling that to undertake a joyful activity like a wedding would have felt so wrong.” (Susan Orlean, 16:41)
• The eventual wedding, months after September 11, becomes a moment of communal catharsis and celebration.

6. The Trauma of California Wildfires

[20:18–25:56]

• Orlean describes the harrowing experience of evacuating her LA home during wildfires, drawing parallels to large-scale personal and collective loss:
  • “We spent five years lovingly restoring this mid-century modern house in the Hollywood Hills... And fire is very present as a—I think of it as like a wild animal that roams through LA at all times.”
• She details the immediacy and chaos of evacuation, the blanking of the mind in the face of trauma, and how little can ultimately be rescued:
  • “When it really happens, your mind goes blank. All I thought was, we need dog food, we need to get the dogs in the car and we need to get whatever medications we need. But as far as thinking about material things in the house, as I said in the book, everything was too much and not enough.” (Susan Orlean, 22:58)
• Orlean remarks on the increasing reality of climate disasters and their deep, lingering scars on families and communities.

Notable Quotes & Memorable Moments

• "Luck has been my friend." (Susan Orlean, 04:00)
• "When you hurt people or people hurt you, it tends to have the effect of attaching you more." (Susan Orlean, 06:10)
• "I needed to make some new history for myself…I also felt like I don't want the last person that I slept with to be Peter." (Susan Orlean, 12:43)
• "Fire is very present as a—I think of it as like a wild animal that roams through LA at all times." (Susan Orlean, 20:42)
• "Writing is a job, but for me, it has always felt like a mission...to show how rewarding it is to be open to and curious about the world and how much joy can be found in letting yourself be surprised." (Orlean as read by Zibby, 25:56)

Timestamps for Key Segments

• [01:45] Good fortune and the role of luck
• [04:13] Marriage, heartbreak, and attachment
• [07:56] Reinventing herself in Bhutan
• [15:13] Love story and the 9/11 wedding postponement
• [20:18] Experiencing California wildfires and evacuation
• [25:56] Orlean on writing, empathy, and her mission

Tone & Takeaway

The conversation is candid, warm, and reflective—characterized by Orlean’s humor and willingness to examine both her triumphs and missteps. Listeners journey through milestone moments, both public and deeply private, witnessing how a storyteller finds meaning and connection amid unpredictability.

For readers and writers alike, Orlean’s journey in JOYRIDE (and this episode) is a testament to curiosity, resilience, and the enduring power of narrative.