The Jordan Harbinger Show

Episode 1228: You Cut and Run but Parents Treat Ex like a Son | Feedback Friday
Date: October 24, 2025
Host: Jordan Harbinger
Co-Host: Gabriel Mizrahi

Episode Overview

In this Feedback Friday episode, Jordan Harbinger and Gabriel Mizrahi tackle tough listener dilemmas around dysfunctional family loyalties, difficult friendships, career pivots in the face of financial strain, and the age-old question: when is the best time to travel and see the world? The guys blend heartfelt empathy, sharp advice, and their signature banter as they help listeners dissect core issues beneath the surface of advice-seeking questions.

[01:31] Pre-Question Banter: Gabe’s Baltic Adventures & The Value of Home

Key Points:

• Gabriel is podcasting from Stockholm, recovering from a “booze cruise” between Helsinki and Sweden, expecting chaos but experiencing an uneventful mini-vacation with moments of self-reflection and Zoom therapy mid-voyage.
• The conversation humorously highlights the unpredictability of travel and the toll of constant movement, with Gabe describing hitting a “wall” of homesickness and fatigue.
• Both hosts reflect on the rejuvenating value of staying with old friends, finding “soft landings,” and the importance of occasional rest.

Memorable Quotes:

• Jordan: “It's like the equivalent of I need to get across the room. I'm going to walk on my hands to get there. Like, no, no, no.”
• Gabe: “The weirdest thing that happened on the boat was probably me doing zoom therapy at 9pm from my room.” (07:00)
• Gabe: “I have a whole new appreciation for...sitting down at a dinner table with people you know for years and having a soft landing.” (09:44)

[10:08] Q1: Parents Siding with Your Ex—How to Maintain Boundaries?

Listener’s Situation: A woman left her neglectful, possibly unfaithful partner, found happiness with a new man, but her parents now seem to have adopted her ex. They house him, help him legally, and even seem to prefer his company to their daughter’s. The listener’s attempts at healthy boundaries are met with pressure from family to “forgive and heal,” leaving her feeling unsupported and isolated.

Highlights of Discussion:

• Jordan & Gabriel’s Response:

  • Both are clearly stunned and saddened by the parental neglect and inappropriate emotional behavior recounted by the listener (e.g., kids involved in marital affairs, being left alone for weeks as children).
  • The hosts agree the parents’ choice to side with the ex is deeply bizarre and insensitive, regardless of any unseen circumstances.
  • They discuss possible unspoken dynamics (“Are her parents missing key info about what happened? Are they repeating patterns from their own dysfunction?”) but ultimately conclude the parents’ behavior is out-of-bounds, regardless.

• Advice for the Listener:

  • Accept that proximity to her family may always come with emotional costs, but she can choose which boundaries to set.
  • Learn to politely but firmly deflect family meddling: “I'm going to kindly ask you one time to not pressure me to handle this the way that you want me to.” (19:11)
  • Consider sharing more with her parents about what the ex did and why the marriage ended—if it feels safe—since her secrecy might be part of why they’re siding with him.
  • Ultimately, therapy for herself and her son is a huge win (“Thank you for doing that for us...that’s great news.” (16:06))
  • Empower herself to continually re-evaluate how much contact and vulnerability she maintains with her parents and extended family.
  • Frame her lens not just as “Why do they make me pay the price?” but “How do I keep them from hurting me so much?” The focus shifts from their (unreliable) change to her own empowered choices.

Notable Quotes:

• Jordan: “Your mother and father were not good parents. I can confidently say that a childhood like this has got to leave a mark.” (12:07)
• Gabriel: “She's kind of a victim of her own evolution…the stronger and healthier you become, the more the unresolved stuff crops up.” (18:32)
• Jordan: “There’s a version of this that’s more like Zen acceptance.” (21:21)
• Gabriel: “Their behavior isn’t conscious malice. They're just doing whatever they want, and not thinking about what it means for anyone else.” (22:20)

Timestamps:

• Breakdown of listener’s background: [10:08]–[12:43]
• Hosts' analysis & major insights: [13:19]–[24:25]

[28:22] Q2: How to End a Draining, One-Sided Friendship—Even When Your Friend Is Grieving

Listener’s Situation: A listener has maintained a quarter-century-long friendship with a woman who is self-centered and rude. After suffering a tragically loss (her own son), the friend is even more draining, and the listener feels guilty for wanting out.

Highlights of Discussion:

• The age-old problem: is it wrong to cut ties with someone who’s suffering?
• Jordan is clear—grief does not excuse years of bad behavior.
• Gabriel points out the telling detail that the friend scheduled a deep talk about problems a month out—not really the mark of someone invested in repair.

Advice for the Listener:

• Go into the conversation with low expectations; share your feelings for your own closure, not to “fix” your friend.
• Deliver your message with honesty and non-combative language (“Present her with the facts...but don’t go overboard.” (35:11))
• Sample script provided (see transcript at 35:26 for details): state your appreciation for the history, then the specific issues, and your need for change.
• Be prepared for anything—if the friend is contrite, good; if not, you have your answer.
• Both agree: “Your job is to go on record with her, largely for yourself, and then give her a chance to show you what kind of person she is.” (36:35)

Notable Quotes:

• Jordan: “She's lucky that you've put up with her bullshit for so long.” (30:38)
• Gabriel: “One of the most common red flags ever—being rude to waiters and service people.” (28:46)
• Gabriel: “I think the takeaway here might be: manage your expectations with old Charlene.” (32:24)

Timestamps:

• Setup & initial advice: [28:22]–[31:27]
• Sample script & closure: [35:26]–[37:17]

[39:00] Q3: Stuck in a Trade, Stuck in Debt, Stuck in Self-Doubt—Should I Chase a New Career or Settle?

Listener’s Situation: A 37-year-old father of three is barely getting by financially as a tradesman and has tried to pivot into being a mortgage broker without much success. He worries he lacks ambition and is tempted to give up—but is demoralized at the thought of wasting the energy and money spent on his new credential.

Highlights of Discussion:

• The hosts quickly reframe the “path of least resistance” self-label: “You’re not lazy. That’s not what I’m hearing at all…Your actions don’t match the label you’ve applied to yourself here.” (43:13)
• Unpacks the deeper fear beneath “laziness”—shame, vulnerability, uncertainty.
• The real work isn’t picking trades vs. mortgages, it’s learning to tolerate new, scary feelings and persist through growing pains.
• The solution isn’t looking for a career where everything is “easier,” but rather learning to “build up your capacity to bear them—the uncomfortable feelings.”

Advice for the Listener:

• Identify and confront the feelings you're avoiding (e.g., fear, shame, confusion).
• Stick with the new challenge a bit longer, but talk openly about the feelings that come up; do the work in therapy or with trusted loved ones.
• If, after pushing through the discomfort, mortgages aren’t for you, it’s OK to let go—just don’t quit because of fear.
• “What needs to change is your relationship with yourself.” (48:44)

Notable Quotes:

• Jordan: “It’s not the tasks that we’re avoiding, it’s the feelings that the tasks stir up in us.” (45:13)
• Gabriel: “Ambition is definitely a real quality, but it’s not the full story, and it’s probably not the thing that’s holding him back.” (48:20)
• Jordan: “Give this a real go. Chip away at this mortgage game while you feel these feelings.” (48:44)

Timestamps:

• Listener’s story: [39:00]–[40:28]
• Deep dive into motivation: [43:13]–[47:04]
• Advice, closure: [48:44]–[49:30]

[55:27] Q4: Should I Travel Before or After College? How Young Is Too Young to Hit the Road? (Student, 17)

Listener’s Situation: A 17-year-old torn between the conventional path (college immediately after high school) and his lust for adventure and world-travel, seeks advice: does the order matter?

Highlights of Discussion:

• Both Jordan and Gabriel strongly affirm the immense value of travel “while you’re too young and poor to realize that the whole experience is actually kind of unpleasant, which a lot of rugged travel is. But that’s the price of admission for an experience that is so rich.” (64:32)
• The complications of adult life pile on quickly—the earlier you travel, the lower the opportunity cost and the more open you are to certain transformative discomforts.
• There is no one right way: take gap years, defer college, travel in summers, or after graduation—just generate lots of options.
• Apply to colleges to keep doors open; see if you can defer.
• Gabriel notes, “Don't get too locked into this idea that it's one or the other.” (61:31)
• The life-changing value isn’t just in travel, but in building and maintaining connections along the way.

Notable Quotes:

• Jordan: “Every five-year period that goes by, the level of complication in my life goes up.” (57:05)
• Gabriel: “It's a gift to see the world as early as possible and open yourself up to new influences early on." (62:17)
• Gabe: “Best advice I can give: sit with the question, talk to people, especially older people who have traveled, and just see what your heart is telling you to do—at a stage of life when you can really afford to listen to your heart.” (65:30)
• Jordan: “There’s no magical window. But the types of experiences you tend to have, the time frame you get to fully enjoy them, that does change.” (67:07)

Timestamps:

• Listener’s background: [55:27]–[56:58]
• Advice, anecdotes, closing wisdom: [56:58]–[68:31]

Additional Memorable Moments

• Gabe’s therapy-at-sea anecdote (07:07 & 07:53), highlighting the intersection of modern travel, technology, and self-care.
• The hosts’ riff on induction stoves and hostel life (36:18–36:51 & 63:16–63:54) as examples of their natural, relatable humor.

Episode Takeaways

• With family: Boundaries are essential, even if others don’t understand. Authentic connection sometimes means distance.
• With friends: It’s okay to walk away from relationships that drain you, even if someone is suffering. Deliver your truth kindly and accept the outcome.
• With career changes: The hardest part isn't learning new skills, but tolerating the discomfort of change. Face the feelings, don’t just rearrange your résumé.
• With travel and life choices: Act early if you can, but don’t stress over perfect timing. Growth never goes out of style.

Useful Segments & Timestamps

• [10:08] – Family treating the ex better than their own daughter
• [28:22] – Considering ending a long, draining friendship
• [39:00] – Career crossroads and overcoming self-doubt
• [55:27] – When is the best time to travel?

Tone

Warm, direct, slightly irreverent, generous with empathy but unafraid to call out harmful patterns. The hosts balance humor (“more like Princess Cruises with that luggage,” “simmering pot of dick”) with thoughtful, actionable advice.

Notable Quotes

• Jordan: “She’s lucky you’ve put up with her bullshit for so long.” (30:38)
• Gabriel: “People who want you to heal and forgive, but have no appreciation for the history or details—ridiculous.” (17:30)
• Jordan: “If they're not going to change…she has to change.” (23:12)
• Gabriel: “The opportunity cost is about as low as it’s ever going to get for you at your age.” (65:30)