Laugh Lines with Kim & Penn Holderness

Episode: "Open Door, Not Empty Nest with Gretchen Rubin"

Date: September 16, 2025
Guest: Gretchen Rubin

Episode Overview

In this heartfelt and humorous episode, Kim & Penn Holderness open up about the emotional rollercoaster of sending their firstborn to college, exploring the transition from “empty nest” to Gretchen Rubin’s “open door” approach to parenting. With special guest Gretchen Rubin—bestselling author and happiness expert—they unpack the complex feelings, habits, rituals, and identity shifts involved in this new parenting chapter. The trio delves deep into how to cope, reframe the experience, and find fresh happiness, all while maintaining their signature wit and warmth.

Key Discussion Points and Insights

1. The Emotional Impact of the College Drop-off

Timestamps: 05:53 – 09:59

• Kim’s honesty: Kim shares how she’s been struggling since dropping off their daughter at college, comparing the aftermath to "summer camp should be over and I'm gonna go pick her up." The reality of the absence hits hardest on weekends, especially Sundays, which used to be reserved for mother-daughter rituals.
  • “It was like, oh, crap. I thought I was getting better. Like, I was bragging to my friends. I'm like, I haven't cried in two days.” (07:31, Kim)
• Penn’s affirmation: Penn reassures Kim, normalizing her feelings and emphasizing that sadness and longing are to be expected.

2. Listener Connections and Solidarity

Timestamps: 12:09 – 13:47

• Voicemail from a listener: A mom shares her own experience dropping off her son, echoing Kim’s feelings and highlighting the universal nature of the grief and pride of launching a child.
• Dad wisdom: Penn recounts the advice his father gave him: “Always be honest and don’t get pregnant,” using humor to lighten the mood.

3. Reflection on COVID and Family Content Creation

Timestamps: 15:04 – 18:15

• The hosts reflect on how their content and family dynamics shifted during the pandemic, with Gretchen noting how it “really defined the Holderness family as like, let's make people laugh.” (17:01, Gretchen Rubin)
• They discuss the possibility of AI and the future of in-person connections.

4. Introducing Gretchen Rubin and the "Open Door" Framework

Timestamps: 22:24 – 25:06

• Gretchen reframes the "empty nest" as an “open door,” emphasizing hospitality, ongoing connection, and new beginnings:
  • “I like open door because it captures this idea of hospitality... and a sense of possibility, whereas empty nest just feels very left behind.” (24:09, Gretchen Rubin)

5. The Role of Habits and Self-Care in Emotional Transitions

Timestamps: 25:56 – 33:21

• Self-nurturing habits: Gretchen explains she leans on healthy habits (sleep, exercise, connecting with loved ones, reading childhood books) during stressful times.
• Coping strategies: Kim seeks advice on breaking the cycle of comfort eating and doomscrolling.
  • Gretchen distinguishes between treats that truly refresh versus those that leave you feeling worse:
    • “We really want to say, oh, going for a long walk is going to make me feel better. Sitting down and doom scrolling is going to make me feel worse. Let me make a choice based on that.” (27:05, Gretchen Rubin)

6. Creating New Rituals and Traditions

Timestamps: 33:55 – 36:56

• Gretchen advocates for “new rituals”:
  • “We say goodbye to our children many times... marking these transitions can be really great.” (36:56, Gretchen Rubin)
• She shares her own practices: a "signature shoes" shopping trip and plans for a special Fourth of July.

7. Healthy Communication and Boundaries with College Kids

Timestamps: 37:09 – 40:38

• How often should you check in?
  • “I think once a week is plenty, really.” (37:52, Gretchen Rubin)
  • Open-ended, non-invasive “check-ins” are healthiest.
• Beware of “interviewing for pain”—a pattern where parents repeatedly fish for negative updates, which can pressure kids to report stress or sadness.

8. Shifting Parental Identity and Finding a New Self

Timestamps: 43:03 – 45:12

• Reclaim old identities, dig deeper into neglected passions, or cultivate entirely new ones.
  • “I don't know who I am anymore”—how to begin redefining yourself post-kids.

9. The Happiness Project: A Toolkit for Transition

Timestamps: 45:26 – 48:53

• Gretchen explains the Happiness Project and how focusing on two foundational areas—your body and relationships—can help you thrive in this new phase.
  • “Everything is easier when we have energy. And our physical experience will always color our emotional experience.” (45:26, Gretchen Rubin)
  • "The most important thing for our happiness is strong relationships." (47:35, Gretchen Rubin)

10. The Four Tendencies and How Personalities Affect the Transition

Timestamps: 53:02 – 58:13

• Gretchen outlines her Four Tendencies framework (Upholder, Questioner, Obliger, Rebel) and connects it to how parents might handle the “empty nest” differently. Kim is an Obliger, Penn a Questioner.
  • "Obligers... may find it hard to organize their time for themselves because it's an inner expectation." (55:58, Gretchen Rubin)
  • "Questioners... sometimes get up in their heads... But sometimes you do [feel emotions], even if it might not be rational." (57:58, Gretchen Rubin)

11. Managing Mixed Feelings as a Couple—Splitting Ambivalence

Timestamps: 59:17 – 62:30

• The phenomenon of “splitting ambivalence”—when one partner plays the cheerleader and the other the mourner, instead of both feeling the full range of emotions together.
  • “That can be bad because then you start acting out a role... you don’t want to get stuck in those roles.” (59:22, Gretchen Rubin)

12. Supporting Fathers and Diverse Emotional Experiences

Timestamps: 63:08 – 64:34

• Men often lack support structures to process these transitions. The group encourages more open male friendships or simply shared activities as connection.

Notable Quotes & Memorable Moments

• Gretchen Rubin, on the open door concept:

  "I just feel like it has a more kind of... freshness and a sense of possibility, whereas empty nest just feels very left behind." (24:09)

• Kim Holderness, on the loss of routine:

  "Sundays are usually around my family and my kids, happily. And so when she was gone, I was like, whoa, what do I do now?" (60:39)

• Penn Holderness, on splitting ambivalence:

  "I feel like the other person can't be feeling it. They have to, like, wait until they have some time to..." (58:45)

• Gretchen Rubin, on kids’ happiness:

  "We always say, like, parents always say, like, you're only as happy as your least happy child. But I think for some children, it's, I'm only as happy as my least happy parent." (40:29)

• Gretchen Rubin, on new traditions:

  "I'm a huge fan of new traditions. Okay. Oxymoron. But, yeah, they have to start sometime." (33:55)

Key Takeaways

• Reframe “empty nest” as “open door”: Focus on hospitality, transitions, and new opportunities—for both parents and kids.
• Embrace mixed emotions: It’s okay to feel both grief and hope, or sadness and relief.
• Habits matter in hard times: Lean into healthy rituals rather than short-term coping (cake, wine, doomscrolling).
• Create new traditions: Rituals help mark time and give structure and anticipation, even after old ones fade.
• Relationships remain central: Support from friends, partners, and community is vital.
• Redefine yourself: This stage is an opportunity to reclaim old passions or start new ones—it's an identity shift, not a loss.
• Communication boundaries: Give space for kids to experience their new life, and avoid over-monitoring or probing for negative updates.
• Support for fathers: Dads may need intentional opportunities or reminders to connect and process together.

Timestamps for Important Segments

• 05:53 – Kim describes post-drop-off grief and rituals
• 17:01 – Gretchen on the Holderness family’s impact during COVID
• 22:24 – Gretchen Rubin’s introduction
• 24:09 – The “Open Door” vs. “Empty Nest” concept
• 27:05 – Habits for happiness during transitions
• 33:55 – Establishing new family traditions
• 37:52 – How often to check in with college kids
• 40:29 – The pressure of maintaining happiness for/by your kids
• 45:26 – The Happiness Project methodology
• 53:02 – Four Tendencies and parental transition
• 59:17 – “Splitting ambivalence” as a couple after kids leave
• 63:08 – Supporting fathers through the transition

Episode Tone and Style

Candid, empathetic, informed, and consistently lightened with humor and self-awareness—signature Holderness style, amplified by Gretchen Rubin’s wise, accessible expertise.

Further Resources

• Gretchen Rubin’s Books: “The Happiness Project,” “Better Than Before,” “The Four Tendencies,” and “Secrets of Adulthood”
• Happier with Gretchen Rubin Podcast
• Five Things Making Me Happy Newsletter
• Personality quiz & tools: gretchenrubin.com

“We say goodbye to our children many times and... it happens over and over and over in our life as parents.”
— Gretchen Rubin (66:25)

Summary by Laugh Lines Podcast Summarizer, preserving the heart and humor of Kim, Penn & Gretchen’s conversation for empty nesters and open-door parents everywhere.