You Made It Weird with Pete Holmes

Episode: We Made It Weird #142

Date: July 1, 2023
Host: Pete Holmes
Co-Host: Valerie (Val)

Episode Overview

In this deeply candid and characteristically whimsical episode, Pete Holmes and his wife Valerie welcome listeners to an unusually vulnerable “We Made It Weird.” As always, they blend humor, spiritual musing, therapy-level introspection, and relationship banter. The first half leans playful and tangential, riffing on teachers, weird childhood rituals, and body image; the second half dives into real-time unpacking of a significant life decision Val is wrestling with—should she buy a dance studio business or throw herself further into filmmaking? Along the way, Pete and Val deconstruct doubt, creative callings, self-worth, and the messy but essential process of honoring your authentic yes—even (or especially) when uncomfortable.

Pete opens the show urging listeners not to skip the second half: “It's vulnerable and it's crispy and honest, which I think is really special.” (00:20)

Key Discussion Points & Insights

1. Childhood Memories, Teachers, and “Weirdness”

[05:37–25:00]

• Pete and Val reminisce about school experiences, particularly the quirks and misguided moments of memorable teachers.

  • Pete describes a teacher with a walrus mustache—“a human Birkenstock”—who would comment on students’ snack choices: “Chaney, I would think your diet would be a little more eco groovy than a zebra cake.” (11:10, Val quoting teacher)
  • The duo acknowledges how teachers’ eccentricities both annoyed and oddly endeared them.
  • Pete tells a story about a teacher named Sal Lopez, whose inappropriate classroom banter stuck with him for years. “He was shaped like the number eight… like Danny DeVito had a growth spurt.” (15:12, Pete)

• They riff on evangelical youth culture rituals (“see you at the pole”) and the absurdity of Christian insults (“she was being kind of a see you at the pole”—08:53, Pete).

• Both reflect on how our insecurities can manifest as jealousy when others are being authentic and joyful.

  • “Most of the time when someone is like that and I'm grumpy, it's jealousy… It's like, God, I know how that feels. I wish I felt that good.” (13:02, Pete)

2. Spiritual Practice, Perception, and Internal Doubt

[23:22–33:44]

• Pete opens up about his ongoing meditation and spiritual practices, referencing “A Course in Miracles” and comparing perception to the Matrix code—“the cascading code that you see, that is everything” (24:23).

• He relates a recent experience in meditation where a doubting “apparition” of himself appeared in his mind, criticizing his spiritual pursuits as fantasy.

  • “I had this moment where I was like, go ahead [God], it's fine… Everyone dissolves in the heart of God. We all go together or we don’t go at all.” (25:00, Pete)
  • “I saw a translucent me going like, ‘This doesn't work. That's why you're not gonna like, snap out of the dream. There's nothing to wake up from. When are you going to grow up and realize it's just a hobby and stupid?’” (27:16, Pete)

• They reflect on how our inner critic or “protector” tries to shield us from embarrassment and disappointment.

  • “I do think that voice is probably a protector. It doesn't want to be embarrassed.” (31:17, Val)

• The conversation expands into the comfort (and danger) of materialism as a world-view, and the pull between skepticism and “woo-woo” openness.

3. Creative Block, Resistance, and Pursuit of the “Right” Challenge

[43:43–63:55]

• Pete talks transparently about pressures related to the Hollywood strikes and existential financial anxieties, noting that when dreams come true you can paradoxically lose a sense of community:

  • “When your dreams come true… you become a bit of an outlier… What's underreported is when you're outside, you lose the community.” (45:24, Pete)

• Val describes, in real-time, considering whether to purchase a dance studio business:

  • The appeal: having something of her own, contributing financially, being challenged, not defined by Pete’s career.
  • The stress: her own low “pain tolerance” for admin tasks, worrying about whether she genuinely wants the gig, and if it’s the right “yes.”

• Pete, as an Enneagram 3, discusses his low pain tolerance for his wife's distress; Val, as a 9, unpacks how she processes big choices and admits to feeling paralyzed by overanalyzing all sides:

  • "My head will, like, work overtime... I just want to be able to sit in a room alone and think about this." (54:54, Val)

• Both discuss their roles and dynamics in their partnership as the decision weighs on them, noting how support can empower but also unintentionally disempower.

4. The Decisive Moment: Honoring Authenticity and Intuition

[58:53–66:00]

• After two weeks of agonizing, Val describes a breakthrough: when she finally sits alone in silence, clarity comes suddenly and decisively. She realizes the dance studio isn’t her true path right now—the “yes” belongs to her film project.

  • “The answer just totally arrived… When it was a no, not right now, it was just like, yeah, that's right. There was no like, but am I just taking the easy way out? Am I quitting something because it's hard? … this was like a deep, clear, gut intuition thing.” (59:56, Val)

• Pete connects Val’s process to creative resistance, referencing “The War of Art” by Steven Pressfield:

  • “Resistance is like an aspect of your ego... Another thing comes along and you change horses in the stream.” (61:30, Pete)
  • They liken the business opportunity to “the perfect date on paper,” but Val says about her film: “I wanted to sit on his face… there’s an undeniable chemistry.” (64:43, Val)

• Val realizes she’s a “seasonal being” and needs novelty and growth, not long-term business maintenance.

  • “It's one of my favorite things about show business… you do a thing and then it ends… It's always something different.” (63:00, Pete)
  • “I'm a seasonal being… I don't want to be necessarily doing the same thing for years and years.” (63:36, Val)

5. Relationship Lessons & Role Reversal

[66:00–76:00]

• Pete discusses his tendency to avoid discomfort—even when it would help Val grow.

  • “I'm going to work on trying to be more comfortable with you being uncomfortable, because that can be okay.” (73:29, Pete)

• They reflect on their role reversal (“Usually I’m the one ruminating, but this time Val needed to stew”) and agree it was healthy for both.

• They also discuss the challenge and excitement of supporting Val if her movie takes off, including the potential for being apart during a film shoot.

6. Privilege, Opportunity, and Self-Empowerment

[76:21–80:59]

• The conversation concludes with musings on privilege, “nepo babies,” and the reality that opportunity means little without courage and action.
  • “I know hundreds of people that received those privileges… money, support, community, education, access, and did Dick. Most people don’t get in the car… they just love knowing they have one." (77:57, Pete)
  • “If we're talking about Tony Robbins-ing it, it's not a foregone conclusion. Support is essential and we need to give it. But it doesn't mean you don't deserve credit.” (78:52, Pete)
• Pete praises Val's courage to own her creative desire, imagining her as "a blood covered Amazonian warrior with a fresh puma pelt on her back and a vibrating singing beaver." (79:39, Pete)

Notable Quotes & Memorable Moments

• On vulnerability:

  • "It's vulnerable and it's crispy and it's honest, which I think is really special. So be sure to listen to the second half." [00:20 — Pete]

• On quirky teachers:

  • “He had a walrus mustache… he was like a human Birkenstock.” [11:11 — Val on her favorite teacher]

• On spiritual doubt:

  • “That vision of doubt is made of the Matrix code... You’re given awareness and time and space and this fucking insane miracle... and with the ink we write, 'There's no God, there's no point. This is stupid.'” [28:23 — Pete]

• Val on overthinking:

  • “I only see all sides of things, and it can be very paralyzing.” [54:03 — Val]

• Pete on creative resistance:

  • “Resistance is a genius... one of the forms is: another thing comes along and you change horses in the stream.” [61:30 — Pete]

• Val on intuition:

  • “I let my body, like, process it… I went from hours before being like, ‘what am I gonna do?’ to having such calm clarity.” [65:00 — Val]

• On the right opportunity:

  • “It’s like a date where you’re like, ‘He’s perfect on paper’... but the date with your movie is like, I wanted to sit on his face.” [64:43 — Val]

• On privilege and agency:

  • “A lot of people leave that car [privilege] in the driveway. Some people get in the car, and they still deserve credit for getting in the car.” [78:39 — Pete]

Key Timestamps

• Intro & Episode setup – 00:00–05:37
• Riffing: coffee, school, weird teachers – 05:37–25:00
• Spirituality, perception, doubt – 23:22–33:44
• Hollywood strikes / financial anxieties – 43:43–47:45
• Val considering buying a dance business – 48:02–54:00
• Enneagram, processing tough decisions – 54:03–56:30
• Val’s breakthrough: honoring her “no” – 58:53–60:17
• Creative resistance / War of Art discussion – 60:39–63:55
• Seasonal nature & fulfilling creative paths – 63:55–66:00
• Relationship, discomfort, & independence – 66:00–76:00
• Privilege, merit, and agency – 76:21–80:59

Tone & Language

The episode maintains Pete and Val’s hallmark playful, gently self-deprecating, conversational tone. The dialogue is peppered with bits of absurdist humor, raw honesty, and affectionate ribbing. Even as they discuss worries and doubts, there's a spirit of open-hearted curiosity and gratitude.

Final Takeaway

This uniquely candid episode offers a masterclass in real-time self-exploration and partnership—showing how big decisions are rarely clean, how authenticity often requires uncomfortable sorting, and how the best “yes” is the one that survives uncertainty, discomfort, and honest self-inquiry.

“I hope it inspires and comforts... How rare it is in real time to unpack and actually be vulnerable and grow.” [80:46 — Pete]