Why you’re so hard on yourself (and how to stop)


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, a voice inside me snapped back:
“I don’t know. But if you are, you shouldn’t be—because you know better than that!”

It hit me like a punch to the gut.

Even in questioning if I was too hard on myself, I was being too hard on myself!

It was such a perfect illustration of the problem Azul was pointing out. The part of me that thought self-criticism would fix me was actually the part keeping me stuck.

Today, I’m going to show you that while being hard on yourself might feel useful as a Five, it’s actually a sophisticated form of self-protection that’s costing you more than you realize.

The Five flavor of self-criticism

It’s worth noting: lots of types can struggle with being hard on themselves.

But a Five’s self-criticism looks different.

For types like Ones or Threes, self-criticism is often about being good or successful in the eyes of others.

For Fives, it’s about being competent enough to survive.

We criticize ourselves not because we want praise or status, but because somewhere deep down we believe that spotting every flaw, fixing every weakness, and outthinking every mistake is the only way to stay safe.

Self-criticism becomes a survival strategy.
We tell ourselves it’s discipline.
In reality, it’s a form of control.

And the catch is: it doesn’t work.

Why beating yourself up isn’t making you better

When you’re hard on yourself, it feels like you’re holding yourself to a “higher standard.”

But what’s really happening is:

  • You create a baseline of anxiety that slowly erodes your energy and confidence.
  • You train your brain to associate action with punishment, making it even harder to move forward.
  • You stay stuck in self-monitoring instead of learning through experience.

Self-criticism tricks you into thinking you’re improving.

But in reality, it keeps you locked in hesitation, shame, and fear.

A new way to think about self-improvement

Here’s the shift:
Improvement doesn’t come from hating the parts of you that are messy, slow, or imperfect. It comes from working with them.

Fives thrive when we treat ourselves the same way we treat our favorite subjects: with curiosity, patience, and respect.

Imagine if you approached your own growth like an experiment:

  • Observation without judgment: “Hmm, interesting. That didn’t go how I planned. What can I learn?”
  • Iterative improvement: “Okay, version one wasn’t perfect. Let’s try again with what I know now.”
  • Trust in the process: “Mistakes aren’t signs of incompetence. They’re part of the learning curve.”

Self-compassion isn’t laziness. It’s fuel.

It’s what actually gives you the resilience to keep going when things get hard.

Your small step this week

Next time you catch yourself being hard on yourself, pause.

Instead of tightening the screws even more, ask:
“What would it look like to learn from this, instead of punish myself for it?”

Write down your answer.

And if you’re feeling brave, share it in the community.

It’s a small practice, but over time it rewires how you relate to yourself—and how willing you are to keep showing up for your own growth.

Because you don’t need to be harder on yourself to become who you’re meant to be.

You just need to be willing to stay in the game.

Josiah Goff

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