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 ChatGPT experiments), and talk about our current areas of growth. Plus, a tough “Would You Rather?” question that gets right to the heart of the Five dilemma.

IN THIS EPISODE:

🔹 Red, Yellow, Green Check-In – Why Cody’s been low-key overwhelmed and Josiah spiraled from a simple question at breakfast.
🔹 Current Curiosities – Both hosts have been down the ChatGPT rabbit hole, from building home servers to creating custom action figures.
🔹 Debunking the Myth – Do Fives really hate vulnerability, or are we just afraid of being misunderstood and depleted?
🔹 Subtypes and Being Seen – How self-pres and social instincts shape our comfort (or discomfort) with vulnerability.
🔹 Would You Rather – Constant curiosity with anxiety… or total peace with no drive to explore?
🔹 Growth vs Comfort – Josiah talks about adult kickball and the challenge of showing up without overpreparing. Cody shares his reluctant quest to get good at sales—and why he still tears up at award shows.

LINKS & RESOURCES:

💻 Join the Beyond the Mind beta group: enneagramfive.com/beyondthemind
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💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/45

JOIN THE CONVERSATION:

📢 Do you want to be known—but find it hard to be vulnerable? What does that look like for you as a Five? Share your thoughts in the community!

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

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➡️ #27: Subtypes

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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 plunges and community-building, we dive into the vulnerabilities, narratives, and patterns that shape our relationships, and what it looks like to break through them.

IN THIS EPISODE:

🔹 What Is Friendship? — Redefining friendship as a commitment to grow together, even on different paths.
🔹 Growing Apart (and Together) — Why outgrowing people is normal—and how we’ve navigated seasons of distance and reconnection in our own friendship.
🔹 Inner Circle Criteria — Cody’s candid process for moving people from acquaintance to close friend (including the role of "not annoying him").
🔹 The Five’s Castle — Why we’ve built walls around ourselves and what finally helped us start letting people in.
🔹 Loneliness and Belonging — The pain of feeling like we don’t fit anywhere—and how showing up as our full selves changed everything.
🔹 The Power of Ritual — How a weekly ice plunge ritual (yes, seriously) gave Josiah a real-life model for consistent, embodied friendship.
🔹 Letting People Love Us — From church wounds to substance use to old narratives about being “too much,” we explore what’s kept us from connection—and what’s finally helping us open up.
🔹 Practical Steps for Building Friendships — What’s working for us now, from simple check-ins to shared interests to just being a little more brave.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/44

JOIN THE CONVERSATION:
📢 What’s your experience with friendship as a Five? Has it come easily, or has it felt like a mystery you’re still trying to solve? Come share your story in the community.

The Newsletter Built for Fives

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🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

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➡️ #27: Subtypes

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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 shifted over time, especially in relation to religion, belief, and questioning what’s "real."

Somehow, we also end up talking about remote viewing, telepathic kids, quantum entanglement, and whether intuition is just a hidden ability we’ve ignored. Plus, there's a completely ridiculous moment where we somehow guess each other’s thoughts—twice in a row.

If you've ever wondered whether intuition is legit or just pattern-seeking run amok, this episode might give you something new to think about. 

Or at the very least, you’ll get to hear us blow our own minds in real time.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/43

JOIN THE CONVERSATION:

📢 How do you experience intuition as a Five? Have you learned to trust it, or does logic still win out? Drop a comment in the community!

The Newsletter Built for Fives

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🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

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***

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➡️ #27: Subtypes

***

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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 understanding of time and consciousness.

We also dive into the tension between intuition and logic, the creative insights intuition can unlock, and practical ways Fives can learn to tune in and trust themselves more deeply.

IN THIS EPISODE:

🔹 Struggling to Trust Intuition – Why recognizing and trusting intuition is challenging for Fives who value logic and clarity.
🔹 Intuition vs. Rationality – How intuition often feels irrational, causing internal conflict and doubt about decisions.
🔹 Fear of the Unexplainable – How the inability to logically explain intuitive decisions can lead to shame and self-criticism.
🔹 Creativity and Intuition – How intuition fuels creativity, flow states, and spontaneous inspiration.
🔹 Retrocausality & Intuition – A mind-bending theory suggesting intuition might be insights sent from our future selves.
🔹 Practical Intuition – Examples of intuition guiding career decisions and creative endeavors, along with strategies to strengthen intuitive awareness.
🔹 Learning to Listen – Why practicing intuition in small, low-risk situations helps build trust and reduces anxiety over intuitive choices.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/42

JOIN THE CONVERSATION:

📢 How do you experience intuition as a Five? Have you learned to trust it, or does logic still win out? Drop a comment in the community!

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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***

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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 changes to the podcast, including moving to a weekly format, merging our live episodes into the main show, and shifting our focus toward personal growth strategies for Fives—because understanding yourself is only the beginning.

IN THIS EPISODE:

🔹 Big Changes! Josiah is now full-time with Enneagram Five, the podcast is going weekly, and we’ve revamped our format.
🔹 Red, Yellow, Green Check-in – How are we feeling this week? (Spoiler: Job transitions bring clarity.)
🔹 Current Curiosities – Cody goes deep on Birkenstock clogs (yes, really), while Josiah dives into growing a newsletter and internet marketing strategies.
🔹 Debunking the Five Stereotype – Why Fives can be expressive and outgoing, and how personal growth expands what’s possible.
🔹 Would You Rather? – Unlimited knowledge with no one to share it with, or deep relationships but struggle to learn new things? (We’ve got thoughts.)
🔹 Growth vs. Comfort – The hard but necessary work of feeling emotions in the moment and breaking old Five patterns.

LINKS & RESOURCES: 

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/41

JOIN THE CONVERSATION: 

📢 What’s your take—can Fives really be expressive and outgoing? Have you ever surprised yourself (or others) by stepping outside the stereotype? Drop a comment in the community!

***

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

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***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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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, the impact of anxiety on relationships, and the surprising power of learning to let go. 

IN THIS EPISODE:

🔹 Recognizing Anxiety as a Five – How we’ve unknowingly lived with anxiety for years without acknowledging it.
🔹 Anxiety and the Body – Why Fives often disconnect from physical sensations, and how anxiety forces us back in.
🔹 The Anticipation Trap – How Fives can get stuck in anxious loops about things that never actually happen.
🔹 Coping Strategies – From breathwork to cold plunges to medication, what’s helped us and why.
🔹 The Power of Letting Go – The surprising link between disintegration to Seven and finding freedom from anxiety. 

LINKS & RESOURCES: 

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/40

JOIN THE CONVERSATION: 

📢 What’s your experience with anxiety as a Five? Have you found ways to manage it effectively? Drop a comment in the community!

*** 

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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***

SAY THANKS:

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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 other Fives are saying about this episode? Visit enneagramfive.com/39 to join the conversation!

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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***

SAY THANKS:

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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 enneagramfive.com/38 to join the conversation!

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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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 is for you.

Want to know what other Fives are saying about this episode? Visit enneagramfive.com/37 to join the conversation!

The Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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***

SAY THANKS:

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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 Newsletter Built for Fives

🔹 Get weekly insights tailored for your overactive mind.
🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

📷 Connect on Instagram
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***

SAY THANKS:

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