Enneagram Five Newsletter Issue #018 You’re not lazy, you’re just not resting ↓ This weekend, I’m renting a local Airbnb and having a bro weekend with a few of my oldest friends. No responsibilities. No kids. Just video games, junk food, and goofing off like it’s 2004. It’s a Father’s Day gift to myself and honestly, a survival strategy. Because as a Five, I’ve learned something the hard way: most of the things I do to “rest” don’t actually help me recover. They just keep me comfortably...
5 days ago • 2 min read
Enneagram Five Newsletter Issue #017 Why being the “smart one” is a trap ↓ Growing up, I never felt like I fit in. I chalked it up to being wired differently. I was analytical, introspective, always thinking a few layers deeper than everyone else seemed to be. And eventually, I decided that maybe I just wasn’t meant to belong. But that wasn’t the full story. What I didn’t realize back then was that I had stopped trying. Not because I didn’t care, but because I cared too much. I was terrified...
12 days ago • 2 min read
Enneagram Five Newsletter Issue #016 You’re not stuck because of lack of discipline ↓ For most of my life, I struggled to consistently exercise. I knew it was good for me. I had all the information. I even paid for personal training. But it never stuck. Because deep down, I didn’t believe I was the kind of person who enjoyed working out. I told myself I wasn’t built for it. That I was too in-my-head. That it just wasn’t me. Then one day, I tried something different. I started telling myself:...
19 days ago • 3 min read
Enneagram Five Newsletter Issue #015 Boredom isn't the problem, it's the answer ↓ As you already know, the mind of a Five is both a refuge and a trap. We retreat into it to feel safe, in control, and less vulnerable. But the more we stay in our heads, the harder it becomes to inhabit our lives. Being present challenges that habit. It asks us to stop analyzing and start experiencing. To be with what is, without escaping into thought. And the doorway back to presence often starts with something...
26 days ago • 3 min read
Enneagram Five Newsletter Issue #014 Why cringe is the bridge to confidence ↓ Recently, I shared with you how everything in me wanted to skip my first kickball game. New people, loud bar, unfamiliar activity, and my nervous system said nope. But, I went anyway. What I didn’t tell you is what happened next. Each week, the same pattern played out: I’d show up, fumble through, and leave feeling a bit awkward and unsure. I’d second-guess how I acted, what I said, whether I fit in at all. And...
about 1 month ago • 2 min read
Enneagram Five Newsletter Issue #013 The “perfect plan” is a trap ↓ You already know that overthinking keeps you stuck. But if you’re anything like me, even knowing that can become another thing to analyze. We trick ourselves into thinking we need to “figure it all out” before we begin. That once we have a clear plan, once we’ve mapped every step and anticipated every risk, then we’ll feel ready. But what if that moment never comes? The truth about readiness You will never feel 100% ready to...
about 1 month ago • 2 min read
Enneagram Five Newsletter Issue #012 Why Fives resist help (even when we want it) ↓ I always do my own laundry. My wife offers to help sometimes, but I never let her. Part of it is 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 those blue puppy-dog...
about 2 months ago • 2 min read
Enneagram Five Newsletter Issue #011 Why you’re so hard on yourself (and how to stop) ↓ I’ll never forget the first time my author coach, Azul, called me out. We were on a call going over a draft I had submitted. He gave some thoughtful feedback, then paused and gently said:“Josiah, you’re really hard on yourself.” I laughed it off in the moment. But after we hung up, I sat there replaying his words in my head. “Am I really that hard on myself?” I wondered. And immediately, without thinking,...
about 2 months ago • 3 min read
Enneagram Five Newsletter Issue #010 What if your gut is smarter than your brain? ↓ If you're like most Fives, you’re good at seeing patterns. You can talk yourself out of most decisions. And when something doesn’t feel quite right, you start collecting data until you find a reason that does. But what if the discomfort you’re trying to explain is reason enough? This week, we’re talking about something most Fives can have a hard time trusting: intuition. That quiet gut-level sense that...
2 months ago • 3 min read
Enneagram Five Newsletter Issue #009 Overstimulated? Try this sound-based reset. ↓ If you’re like me, you’ve spent much of your life trying to think your way to calm. You analyze. You troubleshoot. You optimize.But your nervous system? It’s still screaming. Unfortunately, we don’t always realize when we’re overwhelmed until it’s too late—until we snap at someone we care about, or spiral into shutdown mode, or can’t sleep because our minds won’t stop replaying everything that went wrong that...
2 months ago • 3 min read