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...
3 days 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...
10 days 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...
17 days 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,...
24 days 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...
about 1 month 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...
about 1 month ago • 3 min read
Enneagram Five Newsletter Issue #008 The surprising shift that happens when you show up ↓ Last week, I did something I really didn’t want to do: I signed up to play adult kickball. And as the game got closer, my brain tried everything it could to talk me out of going. Not because I was tired. Not because I didn’t have time. But because of a very specific kind of internal resistance (one that Fives know well). This week, we’re talking about what happens when you show up—even when every part of...
about 2 months ago • 3 min read
Enneagram Five Newsletter Issue #007 You’re not protecting yourself—you’re neglecting yourself ↓ Last week, we talked about sensory overload: how our nervous systems get overwhelmed and how retreating into our minds feels like the only option. But there’s another layer to this… When we don’t know how to communicate our needs in a way others can receive, we tend to do one of two things: silently endure until we snap, or disappear completely. In both cases, we’re left depleted. And often,...
about 2 months ago • 5 min read
Enneagram Five Newsletter Issue #006 I didn’t realize I was overwhelmed until I snapped at my kid ↓ It happened over tortilla chips. My son was sitting next to me, happily crunching away, and out of nowhere I snapped at him. The sound felt like nails in my brain. He looked up, confused and hurt, and I immediately felt ashamed. He hadn’t done anything wrong. I just suddenly realized how overstimulated I was. My nervous system had been quietly screaming for hours, and I didn’t notice it until...
about 2 months ago • 4 min read
Enneagram Five Newsletter Issue #005 You’re not avoiding people—you’re avoiding vulnerability ↓ As Fives, we have a reputation for preferring solitude. And for the most part, it’s true. We need space to think, to recharge, to exist without external demands. But if we’re honest, there’s often something deeper at play... We’re not just avoiding people. We’re avoiding vulnerability. Emotional and social engagements require openness, which can feel like a threat. Not a physical one, but a...
2 months ago • 3 min read