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Fully Five: A Newsletter for Enneagram Fives

Go from overthinking to fully engaging, without losing your Five edge. Join 700+ Enneagram Fives getting practical, research-based strategies to help you stop retreating and start living, in your inbox for free every Saturday.

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Featured Post

What Fives really fear when emotions show up

Fully Five Newsletter Issue #040 What Fives really fear when emotions show up ↓ Last week, I was on a research call with a Five who admitted something I’ve heard in different words from almost every Five I’ve talked to. She said, “If I let myself feel what’s actually here, I’m afraid it will swallow me. And then if something comes up and someone needs something from me, I won’t have anything left.” She wasn’t talking about a meltdown. She wasn’t talking about panic or rage. She meant ordinary...

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Fully Five Newsletter Issue #000 Having emotions doesn't drain you... suppressing them does. ↓ A few months ago, I hit a wall. I wasn’t tired from lack of sleep. I’d been working out, eating well, keeping my schedule tight. On paper, everything looked fine. But inside, I felt heavy. Sluggish. Like I was trying to run my system on battery saver mode. So I did what most of us do when feel drained: I pulled back. I canceled plans. Got quiet. Tried to “recharge” alone. Except the more space I...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #038 Why movement gives you more energy (not less) ↓ As Fives, we tend to think of rest as stillness. Quiet. Calm. Motionless. But stillness doesn’t always equal rest. Often, it’s just stagnation disguised as recovery. For the past few weeks inside the Fully Five Accelerator, we’ve been running group Pomodoro sessions. Twenty-five minutes of deep work, five minutes of break. Repeat. Simple, but effective. At first, I didn’t want to stop for the break. When I’m in...

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Fully Five Newsletter Issue #037 You’re not indecisive... you’re trying to eliminate regret. ↓ Last year, my son’s bike got a flat. No big deal, right? Just replace the tube. Except it had been decades since I’d fixed one, and I couldn’t remember what kind of tools it needed or which repair kit to buy. So I did what any Five would do: I opened twenty tabs and started researching. I compared patch materials, valve types, CO₂ inflators vs. hand pumps. I read every review like I was studying for...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #036 Why the smartest people usually make the slowest progress ↓ For 12 years, I researched how to become a full-time creator. I read every book, joined every course, listened to every expert who promised to reveal the secret. I built spreadsheets, outlined business models, optimized workflows. I could tell you the pros and cons of every possible platform, content strategy, and monetization path. But I never actually created. Because no matter how much I learned,...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #035 You don’t need more quiet—you need better quiet ↓ As a Five, I take pride in my ability to be still. To retreat. To rest. To think. Solitude feels like a sanctuary in a noisy world. It’s where we recover from overstimulation, reconnect with our inner world, and finally exhale after carrying too much for too long. But sometimes, that same stillness starts working against us. We stop using it to restore and start using it to hide. Today, we’re exploring how to...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #034 Why detachment isn’t strength ↓ As Fives, we tend to take pride in our ability to stay calm under pressure. When things get chaotic, we keep our cool.We don’t melt down. We think clearly. And in a world that often feels emotionally overwhelming, this self-control can feel like a superpower. But here’s where it gets tricky: what looks like resilience is often just detachment. Emotional detachment isn’t bad in itself. It can be useful, even protective. But when...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #033 Your boundaries don’t have to be walls ↓ Quick note: this week's newsletter includes a special announcement from our friend Sam E. Greenberg, so make sure to check that out below. I used to think boundaries were just about saying no. That they were big, bold declarations to the world: “Don’t come any closer.” And in some seasons, they needed to be. I was depleted, overwhelmed, constantly saying yes when I meant no. So I did what most of us do when we first...

A man sitting on outdoor steps, smiling broadly. He has short hair and a beard, and he is wearing a blue plaid shirt. The background is softly blurred, suggesting a sunny day.

Fully Five Newsletter Issue #032 Stop trying to earn joy ↓ I used to think joy was a reward. Something that came after the work was done. After I’d figured everything out. After I’d earned the right to rest. But the more I started paying attention, the more I realized: I wasn’t just deprioritizing joy—I was avoiding it. Not because I didn’t want to feel good. Because joy felt… inefficient. When your default mode is problem-solving, joy can seem like a distraction. A luxury. Something to be...

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Fully Five Newsletter Issue #031 You don’t need to ‘understand’ your emotions to process them ↓ I used to think I had to figure out my emotions before I could do anything with them. Like I had to trace each feeling back to its source, analyze it from every angle, and extract some kind of insight. Only then would I be allowed to feel it. But over time, I’ve learned something that’s hard to accept as a Five: understanding isn’t required. Insight is helpful, yes. But it’s not a prerequisite for...