There’s a version of 2 a.m. that many introverted leaders know too well.

You’re replaying something you said in a meeting. Wondering whether you came across as confident enough. Questioning whether you’re really cut out for leadership.

For a lot of us, anxiety isn’t a moment.

It’s a loop.

And the harder we try to wrestle it into submission, the tighter it seems to hold on.

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My guest this week is Cara Lai—a meditation teacher whose work has appeared on Dan Harris’ 10% Happier. Before teaching mindfulness, she spent years caught in her own cycle of social anxiety.

What she discovered surprised me.

The answer wasn’t more discipline. It wasn’t self-improvement. It wasn’t finding the perfect morning routine.

It was compassion.

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I’ll admit, “self-compassion” can sound a little soft in a leadership conversation.

It didn’t after this one.

Cara’s point is simple: the loop only begins to loosen when we stop trying to eliminate our fear and start relating to it differently.

Instead of treating anxiety like an enemy to defeat, we meet it the way we’d meet a friend who’s struggling.

Everything else—the meditation cushion, the timer, the eight-minute practice—is just scaffolding for learning that one skill.

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The second idea that stayed with me was Cara’s perspective on vulnerability.

Leadership advice often frames vulnerability as something courageous you occasionally choose.

Cara sees it differently.

When leaders can honestly say, “I don’t know,” or “I’m struggling with this too,” they create psychological safety for everyone around them.

That’s not weakness.

It’s one of the strongest signals of confidence a leader can send.

The illusion is that control creates authority.

Often, control is simply what we reach for when we’re afraid.

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The third takeaway is the one I think most people need to hear.

You don’t need an hour to meditate.

You don’t need a cushion.

You don’t need a retreat.

You need a minute.

Maybe eight.

Maybe three.

Cara suggested something wonderfully ordinary: practice while you’re brushing your teeth.

For those few moments, shift from doing to receiving. Notice the sensation of the toothbrush. Feel your feet on the floor. Let yourself step out of planning mode and back into the present.

That’s where the practice actually begins.

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If you’ve ever been the quiet leader lying awake at 2 a.m., wondering whether you’re built for this, I think you’ll find something valuable in this conversation.

Not because it promises to make anxiety disappear.

But because it offers something more realistic—and, ultimately, more powerful.

A different relationship with it.

Listen wherever you get your podcasts.

Connect with Cara:

Cara Lai’s Website

The Introverted Leader

The Way Out of Anxiety Isn’t More Control