Better Problems · Issue 09

A movie set outside my gym. One rumor, one PA, one fist bump.

October 1, 2026 · 4 min read

When was the last time you watched an opportunity walk past and said nothing?

I walked out of the gym last week into a full movie set. Trailers, lights, a PA holding back foot traffic.

My usual move is to find a way in, something personal. A shirt, some jewelry, the shoes. But he worked in production, and production people wear all black, nondescript by design. I had nothing. So what am I supposed to say? Nice eyes 🤷🏽‍♂️

I decided I had to be interesting

I walked up and said, "Hey, I heard you're looking for extras. I started this rumor."

He looked at me. "We are?"

"I dunno. What do you think?"

He was confused, then laughed. I knew I was on.

So I confessed. "No, I'm actually trying to make that rumor up so I can get on set. If you're looking for any extras, just let me know."

"Well," he said, "today's the last day, so we're wrapping up."

"Okay, cool. If anybody calls in sick or can't make it, find me. I'll be here for another hour."

He laughed. We fist-bumped. We went our merry ways.

What is the next time?

If you're afraid to shoot your shot, ask yourself three questions. When is the next time I can pursue an opportunity like this? What can I do almost immediately to pursue this? And if this is not the route I want to take, what route do I want to take?

Take my movie. If I didn't want to ask that guy, there are casting sites you sign up for and pay for. If that feels more comfortable, go for it.

But be honest about what you're choosing. I'd still have to do something uncomfortable, like auditioning, which I have no idea how to do. The discomfort isn't avoided. It's postponed.

You have to try

A seven-second ask is how I got mentioned in Forbes. I was speaking at an event, and a Forbes journalist was in the green room to interview a headliner. He tried to approach them, but they were busy. He said it out loud, so I said, "Well, I'm here." That was the whole ask.

The research backs it up. When people were sent out to ask strangers for favors, they predicted they'd need to approach 20 people to get one yes. The real number was about 10. Across the studies, people underestimated their odds by about half, and face-to-face asks worked best. You are wired to think the answer will be no, and you're wrong about that half the time.

I've made a habit of this. I once asked Charlamagne tha God in a bathroom, "Can I interview you?" I introduced myself to Jason Feifer at my kids' gym class. Same move every time: seven seconds, say the thing.

It even works in hard conversations. The other day I told my wife, "Hey, you probably don't want to hear this right now, but I'm going to try to apologize and see if it lands." I padded the stats in how I set it up. It worked anyway.

The moral: you have to try. If you won't, ask yourself why.

Is it because you might get embarrassed? Maybe you will. But they won't remember your question for the rest of their life.

Is it because you think you're not good enough? The best way to find out is to ask. If they say no, ask why not. Then you know what to work on before the next ask.

Is it because you think the other person is going to say no? They might. But if you ask, the answer is yes or no. If you don't ask, the answer is already no. You're starting at no, so you might as well shoot your shot. You have nothing to lose.

Think about what you're losing by not trying. The speaking engagements you never apply to. The partnerships you never pursue. The hobbies you never go after. The conversations you never have.

Between sets

The rest of my workout, I waited for that PA to walk over, invite me on set, and show me my trailer. It was nice to think about.

This newsletter was written between sets. Literally. I stayed busy between the wanting and the wishing.

Gordie

The production is called Gordie. You won't see me in it, because I didn't get on set.

I still see it as a win, because I tried. They shoot on my street, by my gym, all the time. So going forward, I'm asking every time.

I heard so many stories about this just happening from other Hollywood celebrities, and it just feels to me like, if I try enough, it's inevitable that it'll happen. That's how I felt about so many things. It just seems like, yes, I could be a good fit for this, and yes, I do want this, and it's possible. If I just try hard enough and long enough, it just feels almost inevitable.

This week's card: SHOOT YOUR SHOT

Today, make one ask in person that you have been rehearsing in your head. Not a DM. Not an email. In person. Say what you want plainly. If the answer is no, you spent seven seconds. If the answer is yes, it changes something.

Play guide: Pick the ask you have talked yourself out of at least three times this month. Walk up. Say the words. Then screenshot this card and post what happened, yes or no. Report the attempts, not just the wins.

Now it's your turn. What's one thing you want to shoot your shot on this week?

Try a Send It card on your own decision

Read this issue in the Better Problems archive

Run the test on your own decision.

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Originally published in Better Problems on LinkedIn.

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The three questions and the card are free. The keynote and the call are how I make a living.