Hi Reader,

An old client of mine was constantly terrified of failing.

Every week, she’d bring me a new variation of the same worry:

“What if this product doesn’t work?”
“What if my investors lose faith in me?”
“What if I just… can’t pull it off?”

On paper, she was doing great: Her company was growing fast and had just closed a Series A. Like every founder, she ran into some speedbumps here and there. But even when she succeeded, her anxiety never went away.

Every win seemed to create more fear, not less. And she knew that this anxiety was hurting her company. She was playing to not lose rather than to win.

One day I asked her, “What if your fear isn’t about failure? What if it’s about pleasure?”

She laughed. “What do you mean?”

I said, “You’ve built a life where every time you start to feel good, you find something to be afraid of. What makes you think that’s fear of failure rather than fear of enjoyment?”

She got quiet.

When I asked her to describe what happens in her body when things start going well, she said, “I tense up. My shoulders get tight. It feels like I shouldn’t go there or that there’s no point in going there.”

So I invited her to slow down, breathe, and simply begin to notice what pleasure actually felt like in her body. Within a few minutes, she began to cry.

“It’s weirdly uncomfortable,” she said. “It’s so big that my system doesn’t know how to handle it. It doesn’t feel like I deserve it.”

At that moment, she realized: She felt so unsafe because safety itself felt foreign.

The fear of having nothing to fear

Most people think they’re afraid of failure. But often what they’re really afraid of is what happens when everything is working.

They’re terrified of what is left when there’s no more fight, no more problem to solve.

This can sound counterintuitive. “Why wouldn’t I want to feel good?” is often the response I get.

But if you learned from a young age that to be safe you had to stay alert, deep pleasure and ease can feel foreign, even dangerous.

As a result, we unconsciously recreate struggle: Manufacturing endless stress, sabotaging our joy, and telling ourselves stories about why we just need to stay vigilant... even when the vigilance prevents growth. A soldier who is vigilantly keeping watch is defending, not growing.

The way to work with this is by learning to receive pleasure. It’s like building an atrophied muscle. At first, it feels awkward, even wrong. You might dissociate or feel the urge to run back to what's familiar—even if familiar means anxious.

But just like any muscle, it gets stronger with practice. And as you’re able to allow more ease in your life, you will discover that you have far more energy when you’re not spending all of it creating tension just to feel safe.

Big Love,

Joe

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