In life and business, it’s easy to get caught up in what doesn’t go according to plan. And boy oh boy, have I been guilty of that. A missed goal, a wrong turn, or an unexpected outcome can quickly overshadow the milestones we hit along the way. But when we take a moment to step back, we often see there’s plenty worth celebrating—even when the picture isn’t perfect.
As I write this, I’m sitting in the Rocky Mountains hosting a destination trivia event with Sporcle. It’s something we’d never attempted before. Along with our hotel partner, we envisioned hundreds of fans traveling to a special location for a weekend of trivia and camaraderie playing games all weekend about a niche topic.
The hotel owner, a huge Sporcle fan, had a vision of a full city takeover by trivia enthusiasts. For our first year, we set a bold yet achievable goal: attracting 200-250 attendees. When the event finally arrived, attendance landed closer to 100. At first, we couldn’t help but feel a twinge of disappointment.
But then we paused and took stock of what actually happened.
Just the act of trying something new was a win. We brought together eight of our best staff members to host a unique weekend experience. They are hear, rising to the challenge and have made the event feel big and memorable, no matter how many people attended. That is a win.
And then there was the first night. As we looked out into the room, full of participants laughing, connecting, and celebrating their shared passion, it hit us: they didn’t care about our attendance goals. They were just happy to be there, in a space created for them to fully embrace their fandom alongside like-minded people.
Having a more intimate crowd created incredible opportunities for what we like to call “unreasonable hospitality.” We handed out swag, sat and played games with attendees, and had countless moments to connect on a deeper level.
One of my favorite stories involves my colleague Derek (shoutout to Chief Rabbit). Early on, he introduced himself to a table of four women who had traveled in for the weekend. He offered to help them with anything they needed during the games and our digital answering system. Playfully, they replied, “Well, if you want to buy us a round of drinks, we will take that.”
A few minutes later, Derek spotted them at the bar ordering their round. Without hesitation, he cut to the front of the line, pulled out his credit card, and covered their drinks. They were floored.
That moment wasn’t just about the drinks. It was about making them feel seen, valued, and part of something extraordinary. And that’s a win.
Even more, it reminded us why we were there. It wasn’t about attendance numbers or revenue goals—it was about creating moments of connection and joy. That’s the kind of win I will always take.
It’s a lesson I’ll carry with me: success isn’t always measured in numbers. It’s found in the faces of the people we serve, the moments of joy we create, and the willingness to take risks and try new things.
We took the win—and we’re better for it.
In Practice:
Celebrate Small Milestones: Whether it’s trying a new project or reaching an incremental goal, pause to acknowledge the effort it took to get there.
Shift Perspectives: If something doesn’t meet your expectations, ask yourself, “What went well? What did I learn?”
Focus on Impact: Remember, the people you serve don’t see your behind-the-scenes goals. They see the experience you create for them—and that’s often the biggest win of all.