You’re not socially awkward—you’re emotionally cautious


Enneagram Five Newsletter

Issue #022

You’re not socially awkward—you’re emotionally cautious

In high school, I used to think there was something wrong with me.

I’d go to youth group and feel completely out of place. Everyone else seemed to flow so easily in conversation—making jokes, telling stories, jumping into social games—while I stood off to the side, overthinking every possible thing I could say.

For years, I assumed I was just socially awkward.

But looking back, I wasn’t struggling with social skills. I was struggling with emotional safety.

Social situations didn’t feel unsafe because I lacked words or charm. They felt unsafe because they carried emotional risk: What if I said something dumb? What if I got it wrong? What if someone saw how unsure I felt underneath my intellectual front?

It wasn’t ineptitude. It was caution. And it makes sense.

Today, we’ll explore why emotional caution gets misinterpreted as awkwardness, and I’ll show you how you can begin showing up more fully in conversations without abandoning your sense of safety.

Why social situations feel risky for Fives

As Fives, we tend to approach the world like scientists. We observe, analyze, and test before we engage. That works beautifully in many areas of life, but in social settings, it can backfire.

Because relationships aren’t experiments you can safely observe behind glass. They’re full of mess, emotion, and unpredictability. Which means the more emotionally cautious you are, the more you may default to staying on the sidelines.

But here’s what that can look like from the outside:

  • Quiet in group settings
  • Holding back your perspective until it’s “perfect”
  • Defaulting to logic when conversations get emotional
  • Downplaying personal stories or skipping them entirely
  • Feeling drained after even minor interactions

Over time, this can create a story in your mind that you’re just “not good” at socializing. But that’s not what’s really going on here.

The real issue is trust, and how little of it we extend to ourselves in emotional spaces.

Social caution is a form of self-protection

You might think you’re socially awkward, but really, you’re protecting yourself from exposure.

You’ve learned that emotional openness can backfire. That being seen is risky. That connection requires a level of vulnerability you don’t always feel equipped to handle.

So instead of opening up, you curate.

You stay vague. You stay quiet. You wait until the moment feels completely safe, and that moment rarely comes.

This isn’t because you’re broken.

It’s because you’re wired for safety. And social vulnerability can feel like stepping into chaos.

But here’s the secret: You can train yourself to feel safe enough to open up.

Not all at once. Not everywhere. But in small, low-stakes ways.

A practical way to open up without overexposing yourself

If the idea of “being more vulnerable” sounds terrifying, here’s a reframe that might help:

You don’t need to make some grand confession. You just need to share a little more than you normally would.

Try this script in your next casual interaction:

“This is random, but something I’ve been thinking about lately is…” “That reminds me of something I’ve been wrestling with…” “Honestly? It’s been kind of a weird day. I’ve been feeling _____.”

You don’t have to go deep. You just have to go one layer down.

Think of it like emotional resistance training. You’re not maxing out. You’re just warming up.

And every small rep makes connection feel a little less threatening.

You’re not awkward. You’re discerning.

That social caution you carry? It comes from wisdom.

You know connection is powerful, and potentially painful. You’re not reckless with your inner world, and that’s a strength.

But caution becomes a prison when you never test the lock.

The goal isn’t to become someone you’re not. It’s to let more of who you actually are come through. Because connection isn’t about putting on a show, it’s about offering a signal. And someone out there is waiting to feel less alone by hearing you speak up.

So, pick a low-stakes moment this week to practice sharing one layer deeper than usual.

You don’t have to impress anyone. Just reveal something true.

Josiah Goff

Say hi 👋🏻 on Instagram, Threads, or LinkedIn

Whenever you're ready, here are some ways to go deeper:

Join the Five Community (Free) – Connect with other Fives on the same path. Join here

📘 Get your Personal Growth Playbook (Free) – In just 5 minutes, get a customized plan designed to help you grow as a Five, without feeling like you have to become a different person. Get your playbook

🎓 Master Connection as a Five – Learn practical strategies with The Art of Connection course. Get the course

🧠 Work with Me 1:1 – Personalized coaching to help you break through your biggest challenges. Book a session

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