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 connection, embodiment, and purpose help break the loop.

IN THIS EPISODE:

🔹 Obsession as a Coping Mechanism – How fear, curiosity, or meaning-seeking can launch Fives into obsessive research.
🔹 Personal Rabbit Holes – From sharks and UFOs to ancient civilizations and gorilla sexuality, we share some of our most intense information obsessions.
🔹 Productivity vs. Paralysis – When does research become a tool for action—and when is it just a distraction?
🔹 The Cost of Obsession – How our informational fixations can isolate us, disrupt relationships, and interfere with real life.
🔹 Recovery Tactics – What helps us stop the spiral: embodiment, social anchors, and learning to trust gut feelings.
🔹 Using Our Powers for Good – The surprising ways our research has helped others and even landed us jobs.
🔹 Knowing When to Stop – Why learning to pause is just as important as learning to dig deep.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/48

JOIN THE CONVERSATION:

📢 What’s your favorite informational rabbit hole you’ve gone down? Did it help or hurt? 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.

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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 from learning to feel more deeply.

We also dig into the shadow side of emotional intelligence, the ways different types approach emotions, and practical advice for Fives who want to build this vital skill.

IN THIS EPISODE:

🔹 Defining Emotional Intelligence – What it really means and why it's not just about understanding feelings intellectually.
🔹 Relationships as Teachers – How close relationships with Fours, Twos, and Sixes have accelerated our emotional growth (sometimes painfully).
🔹 Emotional Blind Spots – Real stories about misreading cues, confusing neutrality with happiness, and accidentally sending the wrong signals.
🔹 Building Emotional Intelligence – Why somatic work, creativity, and tolerating discomfort are critical for Fives—and what’s helped us the most.
🔹 Emotional Manipulation – How emotionally intelligent people can sometimes use their skills for manipulation, and how to spot it.
🔹 Moving from Intellectualizing to Feeling – Why staying in our bodies instead of our heads opens a deeper, richer emotional world.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/47

JOIN THE CONVERSATION:

📢 How has emotional intelligence shown up in your life as a Five? Have you found ways to grow it? Share your stories in the community!

The Newsletter Built for Fives

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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 connections, and the emotional work required to sustain meaningful relationships over time. If you've ever struggled with investing in friendships, drifting apart from people you care about, or wondering whether you're too much (or not enough), this one is for you.

IN THIS EPISODE:

🔹 Friendship from the Outside In — What it’s like to be friends with a Five, from the perspective of a Seven and a Two.
🔹 Drifting, Reconnecting, and Reconstructing — Why friendships with Fives often fade and rekindle, and what holds them together long-term.
🔹 Anxiety, Energy, and Avoidance — How social anxiety, overthinking, and energy management affect how Fives show up in friendships.
🔹 From Judgement to Acceptance — How shared religious backgrounds shaped our self-righteousness, shame, and eventual emotional growth.
🔹 The Power of Being Seen — Why honest feedback from close friends is vital—and how it can transform your relationship with yourself.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/46

JOIN THE CONVERSATION:

📣 What has your experience been like maintaining friendships as a Five? Do you relate to the cycles of connection and withdrawal we talked about? 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.

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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
📩 Get the weekly newsletter: enneagramfive.com/newsletter
💬 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.

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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.

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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.
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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.

***

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➡️ #27: Subtypes

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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!

***

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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.

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➡️ #27: Subtypes

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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.

***

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➡️ #27: Subtypes

***

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