Hard work is a virtue… until it becomes a trap.

In this episode, we explore how Fives relate to hard work, motivation, and the stories we’ve inherited about what effort should look like. We unpack our personal histories (lazy labels, blue-collar expectations, engineering hacks, and chronic fatigue) and how all of that shaped our relationship to discipline and purpose.

We also dive deep into the myth of "working smarter not harder,” the allure of flow state, and the surprising ways hard work can become a source of love, not just labor.

IN THIS EPISODE:

• Strategic Laziness — How Fives use systems, automation, and over-engineering to avoid work… and why that’s not always a bad thing.
• Hard Work as Avoidance — Why we sidestep tasks that feel like a grind, and how that resistance often masks deeper fears.
• The Flow State Trap — How chasing peak performance can become its own form of procrastination.
• Redefining Discipline — Moving from obligation to alignment, and why discipline matters even when inspiration doesn't show up.
• Motivation Through Meaning — How caring for others (and ourselves) gives effort a new purpose, from parenting to partnership to podcasting.
• The Work of Love — What diapers, depression, and doing the laundry taught us about what love actually is.
• From Avoidance to Integration — How doing the hard emotional work helped us stop running and start liking ourselves.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/55
📚 Books mentioned:
• The War of Art by Steven Pressfield
• The Creative Way by Seth Haines

JOIN THE CONVERSATION:

📢 What’s your relationship to hard work as a Five?
Do you avoid it? Chase flow state? Redefine it?
Share your story with us in the community!

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***

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➡️ #27: Subtypes

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Fives crave clarity, but expectations make everything fuzzy.

In this episode, we wrestle with how expectations shape our creative process, our friendships, and our self‑story—often without us noticing. We start with the behind‑the‑scenes saga of trying (for the third time!) to record this conversation, then follow the thread into dread before hitting “record,” unspoken agreements in friendship, and how TV taught many of us what relationships “should” look like. Along the way, we share small shifts that reduce spiral time and increase real connection.

IN THIS EPISODE:

• When Expectations Jam Creativity – How pre‑loading a conversation with “it has to be great” creates dread, stalls energy, and makes us over‑analyze instead of talk.
• Friendship Without Guesswork – The cost of unspoken expectations (e.g., slow replies, differing communication rhythms) and the relief of naming needs directly.
• Seeing Yourself Through Someone Else’s Eyes – How imagining others’ perceptions fuels spirals—and simple checks to return to reality.
• Independence Isn’t the Goal – Moving from “don’t burden anyone” to chosen interdependence: sharing burdens to build connection, not to outsource regulation.
• TV-Trained Expectations – The West Wing, Friends, Scrubs, The O.C.—how pop culture scripts set unrealistic standards for friendship, family, and community.
• Proximity and Belonging – Why neighbors and repeated contact create the “just walk in” ease so many Fives want—and how to cultivate it on purpose.
• Comparison, Career, and Age – Spotting the Instagram version of other people’s lives, reframing late starts, and noticing what you actually prioritized.

LINKS & RESOURCES:
📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/54

JOIN THE CONVERSATION:
What expectation are you ready to drop this week, of yourself or someone else? Tell us what shifts when you name it 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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In this live episode, we dig into a common belief about Fives that seems flattering on the surface but gets more complicated the deeper you go. We talk about what listening actually looks like for us, why presence is harder than it seems, and how emotional bandwidth plays into the equation.

We also share what’s been lighting up our curiosity lately (spoiler: it includes alien documentaries, tornado footage, and an obsessive dive into Pokémon Emerald), and debate a Would You Rather that pits emotional exposure against slow internet. It got intense.

To wrap things up, we reflect on where we’ve been growing (and where we’ve been hiding) and what happens when we stop waiting for the perfect conditions and just show up.

IN THIS EPISODE:

• Red, Yellow, Green – COVID recovery, job burnout, and existential aging
• Current Curiosities – Pokémon stats, weather disasters, and the nerdy joys of lighting setups
• Myth Busting – The difference between appearing to listen and actually being present
• Would You Rather – Hourly emotional check-ins or research with throttled internet? You have to pick.
• Growth vs. Comfort – Hosting with no agenda, launching without overthinking, and saying yes before everything feels safe

LINKS & RESOURCES:

🚀 Join the Fully Five Accelerator: enneagramfive.com/ffa
📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/53

JOIN THE CONVERSATION:
Do you consider yourself a good listener as a Five? What makes it easier (or harder) for you to stay present in conversation? Come share your experience 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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Break free from observer mode with a proven growth framework and the weekly support of people who truly understand how your Five brain works.

🚀 ​See if you're ready for FFA

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RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

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SAY THANKS:

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Fives often imagine themselves outside of time, but aging has a way of forcing us back into reality.

In this episode, we explore how Fives experience getting older—from bodies that don’t bounce back the way they used to, to the existential weight of midlife, to the surprising hope that comes with perspective. We share stories about family, health, autonomy, and regret, but also about the freedom, wisdom, and community that emerge when you stop trying to outrun time.

IN THIS EPISODE:

• The Rift Between Mind and Body – Why our inner age often feels younger than our actual age, and how the body reminds us otherwise.
• Facing Mortality – From fears of losing parents to confronting our own decline, what aging stirs up for Fives.
• Autonomy and Midlife Crisis – How delayed gratification can turn into foregone gratification, and why midlife forces us to re-evaluate.
• Regrets and Religious Conditioning – How past choices shaped our thirties, and what it means to soften instead of harden as we grow older.
• Community and Connection – Why relationships, novelty, and shared experiences keep us alive and vibrant.
• Hope for the Future – Stories of resilience, learning to take care of ourselves, and what we’re actually looking forward to in our forties and beyond.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/52

JOIN THE CONVERSATION:

📢 What’s your experience of getting older as a Five? Do you feel younger in your mind than in your body, or the other way around? 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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RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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Some people think procrastination is just poor time management, but for Fives it’s often much deeper.

In this episode, we explore how procrastination shows up for us in uniquely Five ways, from building things up in our heads until they feel impossible, to putting off the projects we care about most because they expose our deepest fears and insecurities. We swap ridiculous (and relatable) stories, dig into the hidden reasons we delay, and share the mindset shifts and habits that have actually helped us follow through.

We also talk about the surprising role of friction, how “just five minutes” can break the cycle, and why sometimes the best way to beat procrastination is to take the focus off yourself.

IN THIS EPISODE:

• Ridiculous Procrastination Stories – From expired tags to year-long delays on a two-minute phone call, and what these moments reveal about our thinking.
• Layers of Delay – How fear, insecurity, and perfectionism intertwine to keep us from starting (especially on the things that matter most).
• The Inconvenience Factor – Why even tiny deviations from our plan can feel like massive obstacles.
• Facing the Gap – The discomfort of starting when your current skills don’t match your vision—and how to move through it.
• Removing Friction – The power of shaping your environment so starting feels effortless.
• Raising the Stakes – Using public deadlines and external accountability to get things done.
• Shifting the Focus – How putting attention on helping others can quiet the inner critic.
• The “Five-Minute Rule” – The small, simple commitment that can break the spiral of inaction.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/51

JOIN THE CONVERSATION:

📢 What’s your most absurd example of procrastination as a Five? And what helps you finally take action? Share your story 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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***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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CONNECT:

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SAY THANKS:

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Fives are known for their sharp minds, but does that mean we think we’re smarter than everyone else?

In this live episode, we take on a common misconception about Fives—arrogance—and explore where it comes from, why it isn’t the whole story, and what’s really going on beneath the surface. Along the way we share personal updates, talk about growth edges, and wrestle with a brutally hard “Would You Rather?”

IN THIS EPISODE:

• Red, Yellow, Green Check-in – Why both of us are finally feeling green again (after months of chaos) and what’s been shifting behind the scenes.
• Current Curiosities – Cody’s deep dive into Call of Duty loadouts, Josiah’s obsession with Bitcoin tech (and Cody’s honest boredom about it).
• Myth Busting – Do Fives really think they’re smarter than everyone else? How pattern recognition, fear of incompetence, and over-reliance on intellect fuel this stereotype.
• Would You Rather – Speak every thought out loud in real time, or never be allowed to explain your reasoning ever again?
• Growth vs. Comfort – How we’re leaning into emotional vulnerability, building physical fitness habits, and still avoiding certain growth edges.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/50

JOIN THE CONVERSATION:

Do you ever feel like people assume you think you’re smarter than they are? How do you handle that tension? Share your experience 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.

***

JOIN THE FULLY FIVE ACCELERATOR (FFA):

Break free from observer mode with a proven growth framework and the weekly support of people who truly understand how your Five brain works.

🚀 ​See if you're ready for FFA

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

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SAY THANKS:

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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 navigating motherhood as a Five. Whether you’re a Five parent yourself or trying to understand one, this conversation pulls back the curtain on what it’s really like to raise kids as a deeply introspective, energy-conscious, intellectually driven Five.

IN THIS EPISODE:

🔹 Default Parent Syndrome – Why being a Five mom often means being the default parent—and how that impacts your energy, identity, and sanity.
🔹 Sensory Overload & Rage – The lesser-known side of Fives: what happens when you can’t escape and everything’s too much.
🔹 Guilt, Shame, and Nontraditional Roles – From not cooking to setting hard boundaries, the tension between how we parent and how we think we “should.”
🔹 What Fives Bring to the Table – The gifts of deep listening, strong memories, curiosity, and the refusal to parent based on trends.
🔹 Partner Dynamics – Navigating life with assertive kids and extroverted spouses, and learning to advocate for your needs.
🔹 Community & Complexity – Why finding parenting community can be hard for Fives—and why it’s still worth it.

LINKS & RESOURCES:

🌀 Sam’s work: https://enneagramsexpert.com/
🌱 Melissa’s coaching: https://enneagrampaths.com/
📩 Join the weekly newsletter: https://enneagramfive.com/newsletter
💬 Join the community: https://enneagramfive.com/community
🗒 Full transcript and show notes: https://enneagramfive.com/49

JOIN THE CONVERSATION:

📢 Are you a Five mom, or parenting with one? What parts of this conversation resonated with you? Come 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.

***

JOIN THE FULLY FIVE ACCELERATOR (FFA):

Break free from observer mode with a proven growth framework and the weekly support of people who truly understand how your Five brain works.

🚀 ​See if you're ready for FFA

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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CONNECT:

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***

SAY THANKS:

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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

🔹 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.

***

JOIN THE FULLY FIVE ACCELERATOR (FFA):

Break free from observer mode with a proven growth framework and the weekly support of people who truly understand how your Five brain works.

🚀 ​See if you're ready for FFA

***

RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

***

CONNECT:

📷 Connect on Instagram
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💼 Connect on LinkedIn
📹 Subscribe on YouTube

***

SAY THANKS:

💜 Leave a review on Apple Podcasts
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