Being Bold
Why Taking a Risk Sometimes Creates the Only Magic That Matters
December 2025. I’m driving home from a holiday gig, the kind I’ve done dozens of times. Same client. Same group. Same general rhythm to the night. These are the gigs that are comfortable. Tonight, something happened that I can’t stop thinking about because it only worked once. And that’s exactly why it mattered. I want to talk about taking risks in your work. The kind that can’t be repeated. The kind that reminds you why live performance is still special.
I was working a small group when a guy, let’s call him Dan, started engaging. Dan was skeptical, but in an enjoyable way. He wasn’t combative. Arms crossed, smile just barely there, eyes watching closely. At some point, I asked him to think of a celebrity. But for whatever reason, I genuinely couldn’t get it. I tried. I missed. I stalled. And eventually admitted defeat. I told him, honestly, “I can’t get it.”
Dan didn’t believe me. He kept saying, “No, no, you’re gonna get it. This is all part of the act.” And I had to double down and say, “I promise you, I’m not. I’m not going to get this.” And that was that. On paper, that should’ve been the end of the moment. That happens sometimes in live performance. You take the loss and keep going. But as I walked away from that group, something started forming in my head. What if the trick wasn’t over?
After the interaction ended, I circled back briefly and asked him one last question, quietly, without any fanfare: “Who was the celebrity?” He told me: Josh O’Connor. Now, here’s where things shift. In my case I keep a small photo printer. It’s not part of a set routine. It’s there for special situations where something could become unforgettable. I pulled out my phone, found a photo of Josh O’Connor, printed it, and wrote two things on the back: the words “Nailed it.” My original thought was to try to get this into his pocket. But as I watched Dan move through the room, I realized that would be a terrible use of my time. I could spend the rest of the night stalking one guy, waiting for the perfect moment, or I could do something smarter. I could ask for help.
So I pulled aside one of Dan’s friends. Someone who knew my style and trusted me. I showed him the photo and said, “Do you think we could get this into his pocket?” He paused for a second and said, “Actually… he keeps his Zyns in his pocket. Do you want me to put it in the tin?” And immediately, I said yes. That was the risk. Because once I handed that photo to someone else, I lost control. I had no way of knowing if it would work. And importantly, this wasn’t a trick I could repeat. This was a one-shot decision.
The photo was planted. I went back to working the room. I didn’t watch. I let it go. About fifteen minutes later, Dan came running up to me. He was holding the photo. He stopped the group I was with and said, “I don’t know how this happened. But this guy made a photo of the celebrity I was thinking of appear inside my pocket. Inside my Zyn tin.” He told the story like he had just witnessed a miracle. He hugged me. And I can guarantee you that he talked about that moment for the rest of the night. Here’s the important part.
I’m never going to perform that trick again. At least not the same way. Not consistently. And that’s exactly why it worked. We spend so much time in magic trying to make things repeatable. We want methods we can trust. And that’s all important. But there’s another layer to this work that doesn’t get talked about enough. Sometimes the most meaningful moments come from decisions you can’t replicate. Moments where you choose boldness. Tonight, I chose to take a risk knowing it might not pay off. I chose to trust someone else. I chose to let go of control. And in doing so, I gave one person a story they’ll probably never forget.
That’s the part I keep coming back to. If I hadn’t made that choice, the night still would’ve been good. I still would’ve done strong magic. But I wouldn’t have this story. And this is bigger than magic. Whether you’re an athlete, a musician, an artist, a performer, there are moments where playing it safe keeps you moving forward, but it doesn’t move anyone else. And then there are moments where one bold decision creates something that couldn’t have existed any other way. You can’t plan those moments. You can only recognize them when they appear and decide whether or not to step into them.
Tonight reminded me that sometimes the best work we do is the most human. Those are the moments people remember. Because sometimes, the magic isn’t in the method. It’s in the decision.
’Til next week, keep driving!
Jason