Enneagram Five

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, conspiracy rabbit holes, and the paradox of being both empowered and paralyzed by too much knowledge. We also look at what pulls us out—how conne...

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 challenging for Fives, and how our relationships have pushed us to grow. We share real-life stories about misreading emotions, struggling to stay in our bodies, and the surprising benefits we've discovered fro...

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 with a Five. From hilarious stories to hard truths, we explore the highs and lows of maintaining deep, long-term friendships—especially when you tend to live in your head.

We reflect on shared histories, missed conn...

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 subtypes shape this dynamic, and what it takes to show up even when we’d rather stay in our heads.

We also check in on how we’re actually doing, share what we’ve been researching lately (spoiler: lots of ChatGP...

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 how our personalities have made friendship harder, how we’ve grown to value it more, and the unexpected ways we’re learning to show up more authentically and connect more deeply.

From childhood loneliness to cold p...

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 how our Five wings shape the way we approach intuition, with Josiah leaning more into the mystical side while Cody stays grounded in practicality. That leads us into a discussion on how our worldviews have shi...

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 positively influence our lives. We share our personal experiences with intuition, examine how it's different from emotional decision-making, and discuss unconventional theories that stretch our underst...

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 experiences of learning to express ourselves in the world. Plus, we introduce a new structure for our live episodes, featuring a mix of community engagement, deep dives, and a little bit of fun.

We also announce huge c...

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 personal stories, unexpected ways anxiety manifests in the body, and strategies that have helped us manage it—including some unconventional ones.

We also dive into the tension between self-reliance and vulnerability, t...

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 Styles.

If the Enneagram has helped you as a Five and you're curious about another framework you can use to better understand yourself, then this episode is for you.

Want to know...

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 Fives.

If you've ever found it difficult to connect with others as a Five, then this episode is for you.

Want to know what other Fives are saying about this episode? Visit en...

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 diagnosed with Asperger's and how that shows up for him as a Five.

If you've ever wondered about the difference between being a Five and being on the spectrum, then this episode i...

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 commitment as a Five, this episode is for you.

Want to know what other Fives are saying about this episode? Visit enneagramfive.com/36 to join the conversation!

The New...

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 fear.

If feeling incompatent has ever held you back as a Five, then this episode is definitely for you.

Want to know what other Fives are saying about this episode? Visit enneagramfiv...

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.

And we talk about Josiah's hair for like 20 full minutes for some reason.

Want to know what other Fives are saying about this episode? Visit enneagramfive.com/34 to join the conv...

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 in the past, and how to find a therapist that works for you.

If you've ever considered therapy as a Five but have been on the fence about it, then this episode is for you.

Note: ...

This is is our most requested episode to date, so we gave the crowd what they wanted.

And it's a bunch of nonsense, so you're welcome :-)

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RECOM...

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 you've ever struggled with depression as a Five, then this episode is for you.

Want to know what other Fives are saying about this episode? Visit enneagramfive.com/31 to jo...

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.

If you've ever wondered why one moment you feel like a sage and the next moment like a schizoid, then this episode is for you.

PS. Go follow Sam on Instagram at @ennea_gasm!
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