The Bert Show
Hosted by Pionaire Podcasting
Episode: Full Show PT 3 — Friday, December 5, 2025

Episode Overview

This episode dives into the complexities of “quarter life crises” among young adults, featuring vivid, real-life stories from both listeners and the Bert Show team. The cast explores the challenges of navigating early adulthood, including family tension, career dissatisfaction, relationship struggles, and listeners’ perspectives on making big life changes. Later, the show pivots into a discussion about “cush” jobs—those rare positions where people get paid to do almost nothing—and ends with a lively segment about repeated engagements and what that might reveal about relationships.

Main Discussion: Quarter Life Crisis

Tracy’s Story: Family, Relationships, and a “Funk”

(01:33–04:10)

• Tracy is feeling “down” due to ongoing conflict with her father who recently discovered she’d been living with her boyfriend, Scott, for a year and a half.
• Her father hasn’t spoken to her directly—he only sends Bible links via email.
• Scott suggests Tracy respond with equally random links, like movie times.
• The situation is complicated by her father’s expectations of “traditional” behavior, e.g., believing Scott should have sought permission.
  • “It’s just like the modern man to let the woman fall on the knife for him.” —Tracy’s father (03:16)
• Tracy counters: “I don’t know if it’s so much as the modern man or a barbaric and archaic view to think that my man needs to fight my battles with my father for me.” (03:42)

Ramona’s Story: Breaking Off, Moving On

(04:34–12:34)

• Ramona, a 25-year-old caller, shares her own moment of crisis. She:

  • Quit a stable job without notice (via email), broke off her engagement, and plans to move back in with her parents in California to return to school.
  • Admits to suffering panic attacks and uncertainty about her future.
    • “I just quit via email. That’s how bad it was. Oh, God.” —Ramona (07:45)

• Ramona’s dilemma sparks the “quarter life crisis” debate:

  • Show members and callers argue over the legitimacy and maturity of her decisions.

Host & Listener Reflections

• Several co-hosts express empathy, admitting to experiencing similar questioning and anxiety at the same age.
  • “I felt like I went through the same thing at 25 and 26…” —Co-host (05:50)
• Others challenge her:
  • “Grow up, don’t quit over email, suck it up. You’re an adult, get your foot out there, open the doors and make a life for yourself.” —Christina, caller (08:23)
  • “Quarter life crisis in this scenario is an excuse. I mean, because you should have... You’re an adult now.” —Co-host (08:07)

Notable Quotes

• “It’s a realization that life’s not going to be as dreamy as you had hoped—even when you were philosophizing in college.” —Co-host (07:09)
• “She’s going to end up being miserable, then wish she had taken the steps when she was younger.” —Tracy (13:46)
• “If you’re not happy in your career and you weren’t happy in your relationship, I think that she’s not happy.” —Co-host (13:14)

Gender & Generational Debates

• Discussion veers into whether it's appropriate for young adults (especially women) to return home after being independent, with some members arguing it’s responsible under certain circumstances.
  • “I was broke in my 20s and never once borrowed money from my parents because I was an adult…” —Co-host (14:56)
  • “Whatever. When I graduated from college, I was like $30,000 in debt, and I wasn’t making that much a year… What was I supposed to do?” —Tracy (14:41)

The Quarter Life Crisis: Is It Real?

(08:23–22:34)

• Discussion includes direct quotes, literature references (the book Quarter Life Crisis), and debate about whether it’s a real phenomenon or just a “tweener stage” between youth and full adulthood.

• Perspectives include:

  • It’s a crucial time for self-discovery, even if the process is uncomfortable or clumsy.
  • Others assert that “everyone feels this, but not everyone runs home to their parents.”

A Listener’s Bold Moves:

• Ramona’s decision to break up, quit her job, and move home is called both courageous and, by some, impulsive.
• The show collectively agrees, however, that most people in their twenties go through some version of these doubts and that, in two years’ time, each person will be quite different.
  • “In 24 months, she’s gonna be a totally different person.” —Co-host (20:33)

Segment: Cush Jobs—Getting Paid to Do Nothing

(25:15–33:03)

• The conversation turns to people who make a full-time living from jobs with almost no actual work:
  • Stories include someone paid to simply “be in the office,” another recounting how an entire government team has no tasks but can’t be fired (25:15–31:17), and an intern reading books hidden under sales displays.
  • “I get my paycheck couriered to the office… I can do anything I want.” —Tammy, caller (27:41)
  • “I make $500 a week, tax free, just to sit around and do nothing.” —Mary, caller (32:50)
• Hosts and listeners agree that, long-term, this is not satisfying—even if the pay is good.
  • “I know it sounds like a dream thing, but I would… No, I couldn’t do that. I can’t just have nothing to do and be satisfied.” —Co-host (32:40)

Relationships: The Serial Engager

(33:44–40:09)

• The cast discusses the story of Nicky Hilton marrying someone previously engaged multiple times, pondering whether repeated broken engagements are “red flags” in relationships.
  • “Would you break off the relationship knowing that chances were pretty good once you got engaged, they were gonna ask you anyway?” —Host (35:22)
• Callers weigh in:
  • Some say prior engagements mean someone is “afraid to be alone” or “chasing excitement.”
  • Others, like Charity (engaged five times!), say a proposal without a ring doesn’t count, and sometimes “serial engagement” is just about stringing out the relationship.
    • “They feel like if you say you’re engaged, it’s like—okay, yes, we’re finally going to do it. And then… I’m like, okay, I don’t have time for this. I don’t have a ring. You’re not showing me anything. I’m gone.” —Charity, caller (39:12)

Notable Quotes & Moments

• Tracy’s Father on Modern Relationships:
  “It’s just like the modern man to let the woman fall on the knife for him.” (03:16)

• Ramona’s Quarter-Life Epiphany:
  “I don’t hate it. I just kind of fell into it.… If I decide to change careers, I kind of just need to go back to school.” (07:17)

• Listener Christina’s Tough Love:
  “Grow up, don’t quit over email, suck it up. You’re an adult, get your foot out there, open the doors and make a life for yourself.” (08:23)

• On Cush Jobs:
  “She shops online all day and does the Internet part of my research papers. It’s kind of ridiculous.” —Elon, caller (29:07)

• Charity on Engagements:
  “If you don’t have a ring, you’re really not engaged.… He don’t want to marry you.” (39:12)

Segment Timestamps for Reference

• Quarter Life Crisis Introduction / Tracy’s Story: 01:33–04:10
• Ramona’s Call & Crisis: 04:34–12:34
• Listener Reactions / Quarter Life Opinions: 08:23–22:34
• Cush Jobs / Boring Work: 25:15–33:03
• Repeat Engagements / Relationship Red Flags: 33:44–40:09

Final Thoughts

• The show provides a nuanced, often humorous look at the struggles facing twenty-somethings and the tricky path to adulthood. There’s a consensus that while everyone inevitably faces discomfort and questioning, maturity lies in how one handles those moments—whether with impulsivity or with reflection and resolve.
• The candid, back-and-forth style, open phone lines, and deeply relatable stories make this episode a dynamic portrait of the messiness of growing up—one that leaves listeners laughing, wincing, and reflecting in equal measure.