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,...
5 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...
12 days 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...
19 days 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...
26 days 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 1 month 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 1 month 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...
about 2 months ago • 3 min read
If you've ever hesitated to take action because you felt unprepared, you're not alone. Cody and I sat on the first Enneagram Five podcast episode for six months because I was convinced we needed perfect systems in place before releasing it. I kept waiting to feel "ready," but that moment never came. When we finally put it out, it took off like a rocket all on its own, proving all my extra preparation was just a way for me to torture myself. That's when I learned that waiting for the perfect...
2 months ago • 3 min read
Last time, we explored why we get stuck in our heads as Fives, even when it makes life harder. But there’s a lingering question: How do you engage more fully with life without betraying who you are as a Five? That’s what we’re diving into today. The double-edged sword of intellectual identity If you’re like most Fives, your intellect is more than just a tool—it’s how you understand yourself. Your curiosity, your ability to analyze, your relentless pursuit of knowledge. These aren’t just...
2 months ago • 3 min read