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Fully Five: A Newsletter for Enneagram Fives

Go from overthinking to fully engaging, without losing your Five edge. Join 580+ 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

You're not an overthinker—you're an emotional escape artist.

We don’t retreat into our minds simply because we love thinking. We do it because thinking feels safer than feeling. We tell ourselves we’re just “rational” people—objective, logical, detached. But that’s only part of the story. Beneath the surface, something else is happening: we’re using our minds as bunkers to keep us ‘safe’ from emotions. Today, I’m going to show you why this habit is isolating you and how to break free from it so you can live more fully. Overthinking isn’t about loving...

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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...

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 #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...

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 #030 The real reason you still haven’t started that thing ↓ I used to think I was afraid of failing. That if I took action (put something out there, started the project, joined the conversation), I’d mess it up. Look foolish. Prove I wasn’t as competent as I hoped. But over time, I realized something else was going on. I wasn’t afraid of failing as much as I was afraid of what would happen if it worked. Because I’d been down that road before... the one where...

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 #029 Your nervous system isn’t broken, it’s sensitive by design ↓ I have a confession: I always sit facing the exit when I go places. And when I can’t, I feel a constant tingle in the back of my neck. It’s a habit from childhood, something about needing to know I could leave if things got too intense. But the truth is, it’s not just a habit. It’s a nervous system strategy. As a Five, I’ve always been sensitive to my surroundings. Too much noise, too much emotion,...

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 #028 Stop rehearsing in your head ↓ Have you ever wondered what it would feel like to step into the world with confidence, not second-guessing yourself, but energized, engaged, and fully present? Yesterday, we had our very first Accelerator call, and it taught me something incredible about what happens when a group of Fives show up for each other. We open up, big time. And even better: it energizes us and boosts our confidence to open up in other parts of our...

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 #027 You don’t need more motivation—you need better energy management ↓ For most of my life I thought I was lazy. Finding motivation to do anything other than binge-watch anime felt like a herculean task. I struggled to make meaningful progress on any of my goals. I could sleep 18 hours and still feel tired the next day. It took everything I had just to get out of bed in the mornings and go to work or school. I hated this about myself, but I just accepted that’s...

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 #026 Why your mind won’t let you rest ↓ If you’re like most Fives, relaxation isn’t relaxing. It’s unsettling. You sit down to rest, and your mind instantly starts working. Tasks you forgot. Problems you haven’t solved. Loops of planning, fixing, scanning. I recently looked at the answers from the 170 Fives who’ve taken our Personal Growth Playbook questionnaire, and the data is clear: the vast majority of us can’t relax without our minds hijacking the moment. This...

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 #025 Loneliness isn’t the absence of people, it’s the absence of resonance ↓ I’ve never been afraid of being alone. What I feared was being surrounded by people and still feeling lonely. That feeling... the one where you’re in a room full of conversation, but none of it lands, is something most Fives know too well. We crave connection, but not just any connection. We want resonance. The spark you feel when someone meets you in the deep end of an idea, or when...