Episodes

June 10, 2025

Five Moms: What is Motherhood Like for an Enneagram 5?

What happens when you're a Five and a mom? This week’s episode is a special podcast takeover by Enneagram experts Sam E. Greenberg, PhD and Melissa Kircher—both Fives and both moms. They swap stories, laugh about their quirks, and get painfully honest about the challenges and strengths of navigatin…

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May 21, 2025

Informational Obsessions: Why do Enneagram 5s Love to Fall Down Rabbi…

Some rabbit holes are deeper than others, and as Fives we often fall in headfirst. In this episode, we explore the obsessive way Fives pursue information: how it starts, what fuels it, and what happens when it spirals out of control. We share personal stories of late-night research binges, conspira…

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April 29, 2025

Emotional Intelligence: How Do We Develop Empathy and Awareness as an…

We Fives often pride ourselves on intellect, but emotional intelligence is a whole different skill set. In this episode, Sam E. Greenberg, PhD. joins us to explore what emotional intelligence actually means, why it's challeng...

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April 22, 2025

Friends of Fives: What's it Like to Be Lifelong Friends with an Ennea…

Fives often feel like outsiders, but what if the group we’ve always longed for already exists? In this episode, we invite two longtime friends to join us for a candid conversation about what it’s really like to be friends wit...

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April 15, 2025

[LIVE] Do Fives Secretly Want to Be Seen?

In this live episode, we explore a surprising tension many Fives feel: the deep desire to be known and understood, and the equally strong instinct to hide. We unpack what’s really behind our aversion to vulnerability, how our...

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April 8, 2025

Friendship: Why is it Hard to Make Friends as an Enneagram 5?

Fives pride ourselves on independence, but friendship requires letting people in. In this honest and deeply personal episode, we explore what friendship means to us as Fives—and why it’s so complicated. We share stories of ho...

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March 27, 2025

After Thoughts: Intuition

This is an After Thoughts episode, an unstructured, unedited debrief of everything we didn't say in the last episode—this time unpacking our conversation on intuition . And boy, does this one take some turns... We get into ho...

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March 20, 2025

Intuition: Can You Trust Your Gut as an Enneagram 5?

Fives rely on analysis and clarity, but intuition offers something logic can't: a deeper wisdom that defies explanation. In this episode, we explore what intuition is, why Fives struggle to trust it, and how embracing it can ...

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March 13, 2025

[LIVE] Can Enneagram 5s be Expressive and Outgoing?

Can Fives really be expressive and outgoing? The stereotype says no—but we’re here to challenge that idea. In this episode, we unpack the myth that Fives are always quiet, reserved, and withdrawn, and we share our own experie...

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March 6, 2025

Anxiety: How Do We Handle Feeling Anxious as an Enneagram 5? (And Wha…

Fives value logic and control, but anxiety challenges both. In this episode, we explore how Fives experience anxiety, why we often rationalize instead of feeling it, and how avoiding it can make things worse. We share persona...

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April 9, 2024

Attachment Styles

What's your attachment style as a Type 5? In this season finale episode, Sam E. Greenberg joins us again to walk us through Attachment Theory and what we can learn about being a Five by studying the different Attachment Style...

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April 2, 2024

Convenience vs. Connection

What keeps Type 5s from connecting? In this episode, we delve into Josiah's experience of identifying and dismantling the things that were holding him back from connecting with others, and why connection is so important for F...

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March 26, 2024

On The Spectrum

Are you on the spectrum or are you a Type 5? In this episode, we join Sam E. Greenberg to explore the overlap of traits between being a Five and being on the autism spectrum. We also talk through Cody's experience of being di...

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March 19, 2024

Commitment

How do Type 5's feel about commitment? In this episode we share how we've handled various types of commitment as Fives and how we might approach commitment in a way that doesn't burn us out. If you've ever struggled with comm...

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March 12, 2024

Incompetance

How do Type 5s feel about incompetance? In this episode, we delve into why we get so triggered when people around us are incompatent, why Fives have a fear of incompetance, and what steps we can take to start overcoming this ...

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March 5, 2024

Family Dynamics

How do Type 5s handle being part of a family? In this episode, we delve into what family life was like growing up as Fives, how useful the internal family systems framework is, and what we want our own family dynamics to be. ...

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Feb. 27, 2024

Therapy

What do Type 5s think about therapy? In this episode, we sit down with Liz Landry, friend of the show and licensed therapist, to talk through what to expect from therapy as a Five, what has held us back from going to therapy ...

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Feb. 20, 2024

High Fives

What are Type 5s like when they're high? Maybe that's a question you've never asked, but this is our most requested episode. And it's a bunch of nonsense, so you're welcome :-) Want to know what other Fives are saying about t...

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Feb. 13, 2024

Low Fives

How do Type 5s deal with feeling down? In this episode, we dive into what it feels like to be depressed as a Five, various triggers that cause us to feel down, and some techniques we've used to climb back out of the abyss. If...

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Feb. 6, 2024

Levels of Health

What are the nine levels of health for a Type 5? In this episode, we join once again with our good friend Sam E. Greenberg, PhD (a.k.a the Enneagram Sexpert) to deep dive on the levels of health and what they mean for Fives. ...

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Jan. 30, 2024

Conspiracy Theories

What do Type 5's think of conspiracy theories? In this episode, we dig into Josiah's philosophy of conspiracy theories and why they're so important for Fives (and everyone, according to him). So grab your tin foil hat and joi...

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Jan. 23, 2024

Politics

How do Fives feel about Politics? To kick off Season 4, we unleash our inner anarchists and share our own political journeys, as we resist the urge to burn the system down and instead focus on building something new. If you h...

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Sept. 27, 2022

Subtypes

Why are some Type 5's so different from others? In this season finale episode, we bring back Sam Greenberg, aka the Enneagram Sexpert , to deep dive on the Social, Sexual, and Self-Preservation subtypes of Type 5 and how inst...

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Sept. 20, 2022

Uncertainty

How do Type 5's deal with uncertainty? In this episode, we talk about how we handle uncertain times as fives and what we can do to thrive rather than spiral. Want to know what other Fives are saying about this episode? Visit ...

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