What Are You Avoiding Right Now?

“The best things in life don’t scale.” — Ryan Levesque

This Week’s Scare Your Soul Challenge: Do It Tomorrow

Bottom Line: The things you’re proudest of doing today might be the most sophisticated way you’re hiding from the thing that actually scares you.

Dear Courageous Soul,

About five days ago, I gave a keynote at South by Southwest.

For those who haven’t been, it’s an experience unlike anything I’ve ever seen.

Thousands of people descending on Austin, Texas.

Sessions on every topic imaginable, live music everywhere, thought leaders from around the globe.

It was busy, hot, heady, and for me, beyond nerve-wracking.

Not because I lacked confidence in my talk.

But reading the list of other presenters and their topics — mostly about AI — I started to worry.

Would a talk about the most personal, human things about me and about them feel irrelevant?

In a city of Waymos and Tesla robot bartenders, would anyone care about texting a friend five brave things before bed?

In the end, the talk was a major success.

I knew it from the moment I began, in a crowded room on the second floor of the Line Hotel, that this topic, “Microdosing Courage,” would land squarely in the hearts, not the heads, of the audience.

I’m proud to say that it did.

But something happened afterward that I haven’t been able to stop thinking about.

I shared an Uber with a man who had given a talk earlier in the day.

Smart, accomplished, deeply respected in his field. We started talking about my keynote, and he said something that surprised me:

“I don’t think I could come up with five things that scared me today.”

Five brave things. It’s one of my main takeaways from the talk — the practice I’ve shared with my friend Carly for thirteen years now.

So I pushed the string a little. I shared some of the things that had really pushed me that day.

None of them, he said, would have pushed him. He’d felt comfortable all day.

And that was my in.

“I think you might have selected this experience because it felt comfortable,” I said.

“You’re in a room of your peers, talking about something you have mastery over, having great conversations, giving a keynote with slides built just for you. So — if you’re being honest — what are you avoiding right now?”

He thought for a while.

“Well,” he said. “I should be making more calls to my company’s investors. I need to raise another three to four million dollars. And I haven’t made those calls.”

He said he’d probably get to it in the next few months.

Then he said it: “I’m just not a good fundraiser.”

And you could feel it land — on him, not just on me.

He was scared.

This was outside his comfort zone. He knew it had to happen, but there was uncertainty in it, and uncertainty felt hard. It was much easier to spend the day with peers, exchanging ideas about the future.

I asked him: “What would happen if you picked up the phone tomorrow — not in three months — and called one investor?”

“Well... I could do that, I suppose.”

And then there was silence.

A couple of minutes of it, just the two of us in the back seat of an Uber, speeding through the Austin night, while he sat with something he hadn’t expected to find on the way home from a tech conference.

I didn’t say anything else.

He was already doing the work — sitting in the discomfort instead of running from it.

And I knew he would make that call. Maybe not the next morning. But soon. Because once you see the thing you’re avoiding, it’s very hard to unsee it.

That’s what this work is about.

Not standing on a stage. Not big dramatic leaps.

Finding the thing — the relationship, the conversation, the call, the truth — that means everything to you and is sitting on the other side of fear. And just doing it.

Not in three months. Tomorrow.

And then this landed in my LinkedIn inbox, from a woman I’d met at my talk:

Him in the Uber, sitting with a phone call he’d been avoiding for months.

Her in the airport, buying a toothbrush and changing her trajectory.

Two completely different people.

The same process of saying yes to what scares us.

You already know what yours is.

The call.

The conversation.

The email.

The decision.

The trip.

The thing you’ve been telling yourself you’ll get to in a few months.

You don’t need a few months. You need four seconds of honesty.

What would happen if you did it tomorrow?

PS — Everything I shared in my SXSW keynote — the fear response, the daily practice, the framework for finding what you're avoiding and moving toward it — I put it all in one place. It's free. It's yours.

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