Enneagram Five

Has anyone ever told you that you’re not really a Five? In this episode, Cody stages an intervention (armed with four years of transcripts, Enneagram books, and a surprising analysis from ChatGPT) to settle an ongoing debate: Is Josiah actually a Five… or a Three in disguise? What starts as a lighthearted experiment turns into one of the most personal and revealing conversations we’ve ever had about identity, burnout, belonging, and what it really means to grow beyond your type. IN THIS EPISO...

Fives are proud of being “smart.” But what if that thing we trust most is also the thing holding us back? In this episode, we talk about the difference between intellect and intelligence, and why Fives tend to obsess over one while ignoring the other. We get into why being analytical can make you feel powerful but also isolated, emotionally numb, disconnected from your body, and limited in real life. We also share how we’ve been building other forms of intelligence like emotional awareness, b...

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 c...

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 s...

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 e...