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!

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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RECOMMENDED NEXT EPISODE:

➡️ #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.

***

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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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.

***

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
🧵 Connect on Threads
💼 Connect on LinkedIn
📹 Subscribe on YouTube

***

SAY THANKS:

💜 Leave a review on Apple Podcasts
🟢 Leave a rating on Spotify