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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

Privacy isn’t the problem

Fully Five Newsletter Issue #051 Privacy isn’t the problem ↓ For years, I told myself I'm just a “private person.” I like quiet. I like solitude. I like not having to perform socially when my battery is already at 12%. But if I’m honest, that’s not the whole story. A lot of the time, I’m not avoiding people... I’m avoiding the feeling of being seen. Today we’re talking about why vulnerability feels so risky for Fives, what it costs us, and how to practice connection without feeling like...

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 #050 When “fake it till you make it” actually works ↓ For most of my life, “fake it till you make it” sounded like terrible advice. It felt dishonest. Performative. Like pretending to be something I wasn’t yet. And as a Five, the idea of summoning energy or emotion I didn’t genuinely feel always triggered resistance. If it’s not real, don’t do it. If I don’t feel it, don’t express it. Recently, I decided to test that belief. The experiment I didn’t expect to love...

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 #049 You're not actually built to do it all alone ↓ I always do my own laundry. My wife offers to help sometimes, but I never let her. On the surface, it's partly about control. I want things done a certain way. But if I’m honest, it’s more about how accepting help can make me feel: exposed, dependent, vulnerable. Then the other day, my 4-year-old saw the pile of laundry on the bed and asked if he could help. At first I winced, but then he looked up at me with...

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 #048 The subtle cost of "let me think about it" ↓ A few days ago, I caught myself saying, “Let me think about it,” for the third time in the same hour. Not out loud, just internally. It was one of those days where nothing was technically wrong… but everything felt slightly harder than it needed to. By the afternoon, I was tired in that specific way only a Five understands. Not sleepy. Not burnt out, exactly. Just mentally fried. Today we’re talking about the subtle...

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 #047 Which “fact” about you died last year? ↓ You know, I’ve never really been into zodiac stuff. But, a few days ago I saw a post about transitioning from the Year of the Snake to the Year of the Horse, and it hit me harder than I expected. It said: Snake represents “shedding old patterns.” Horse represents “embodiment and action.” And suddenly, 2025 snapped into focus. Last year didn’t feel like steady progress. It felt like being dragged through a series of...

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 #046 Why you hate New Year's resolutions ↓ Every December, I feel the same quiet resistance in my body. People start talking about “big goals” and “fresh starts,” and part of me wants that too. But another part of me is already tired just thinking about it. I don’t actually hate New Year’s. I hate the feeling of signing an invisible contract I'm worried my future self can’t keep. So I stall. I research systems. I compare planners. I write out elaborate strategies...

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 #045 Your life has its own autophagy ↓ For the past few weeks, I’ve been experimenting with a 36-hour fast every Thursday. I finish dinner Wednesday night, don’t eat all day Thursday, and break the fast Friday morning. At first, it was a logistics problem in my head: Will my energy crash? Will I still be able to get work done? Will I turn into a monster around my family by 8pm? But this week, something else became obvious. The fast didn’t just change how my body...

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 #044 You're not stuck because you can't take action ↓ Some of the most exhausting days in my life look, from the outside, like I “did nothing.” I stayed home.I scrolled a little.I thought about things.I imagined different futures.I opened the project, then closed it. By the end of these days I feel drained and disappointed, and the story that shows up is always the same: “I’m stuck. I can't seem to take action on anything.” But if you watch closely, those days...

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 #043 The question you’re not smart enough to ask ↓ Earlier this week, I found myself in a familiar place. Already behind on the things I wanted to finish in December. Frustrated that everything was taking longer than I swore it would. Trying to convince myself that if I could just work a little smarter, I’d catch up. This is one of my default patterns. I overestimate my available capacity. I underestimate the effort a project will take. And when the gap between the...

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 #042 Why you don’t feel grateful (even when you are) ↓ We just celebrated Thanksgiving in the States. Which means many of us spent the week talking about gratitude, thinking about gratitude, or trying to muster up gratitude while sitting at a table full of people who quietly drain the life out of us 😉 And earlier this week, a Five in FFA shared something that put words to a very familiar experience. She said, “I know I’m grateful. I just don’t feel grateful. So...