A Leadership Lesson from Colonial Williamsburg
There's something magical about Colonial Williamsburg in December. The choirs singing, chestnuts roasting over open fires, crowds gathered in anticipation of the Grand Illumination fireworks show—it's the kind of experience that fills your soul with the glory of the season.
But my biggest takeaway this Christmas wasn't the fireworks.
It was a trash can.
Walking back to my hotel through the historic district, I stopped in my tracks. There, beside the glowing fires and bundled-up crowds, sat a rustic wooden barrel—not even a modern trash can, but a vessel with character that fit the colonial aesthetic perfectly. And on top of it? Coffee cups stacked like little soldiers standing at attention. Someone had arranged the overflow so neatly, so intentionally, that it looked almost like art.
Even the Chick-fil-A bag on the ground wasn't tossed carelessly—it was placed, positioned with purpose alongside the other items that wouldn't fit. Behind it all, the beautiful, historic Williamsburg street stretched out, gorgeous lights streaming through the December night—magic and mess existing side by side.
And I thought: Isn't that just like life?
The Trash Didn't Magically Disappear
Here we are in 2026, and guess what? Most of us are still carrying trash from 2025. The disappointments. The unfinished business. The relationships that didn't work out the way we hoped. The goals we didn't hit.
January 1st doesn't come with a cosmic garbage truck that hauls away everything we'd rather forget.
But here's what I learned from that Williamsburg trash pile: There's trash, but it doesn't have to be ugly. Your transitions through the tough stuff should still be beautiful.
It's all about how you position it.
Four Steps to Deal with Your Trash (Beautifully)
1. Pick It Up
You can't organize what you won't acknowledge. That mess from last year? Those failures, frustrations, and fumbles? Pick them up. Own them. Stop pretending they're not there or hoping someone else will deal with them. Leadership starts with taking responsibility for what's in your space—even the stuff you didn't put there. You can't make something beautiful if you won't touch it.
2. Put It in a Place
Everything needs a home—including your baggage. Don't let last year's garbage scatter across every area of your life. Contain it. Maybe that means scheduling time to process it. Maybe it means having that hard conversation. Maybe it means writing it down and deciding what to do with it. Give it a designated spot instead of letting it blow around like litter in the wind. Even a rustic barrel can hold overflow with dignity when someone cares enough to use it.
3. Give It Structure
Think about a clean desk versus a cluttered one. The papers might be the same, but structure changes everything. Stack your trash neatly—like those coffee cups lined up on the barrel lid. What lessons are in that pile? What can be recycled into wisdom? What simply needs to be set aside so you can move forward? Order brings clarity, and clarity brings peace. The mess doesn't disappear, but it transforms into something you can live with—maybe even something that tells a story.
4. Let It Go When the Truck Comes
Here's the thing about trash—it's meant to be temporary. Structure it, yes. Learn from it, absolutely. Make the transition beautiful, by all means. But when the time comes to release it? Let it go. Don't become so attached to your neatly organized baggage that you forget the whole point is to eventually be free of it.
Surround Yourself with Tremendous People
Here's what really struck me about that Williamsburg trash pile: Someone cared. They didn't just chuck their garbage and walk away. They took the extra thirty seconds to stack it with consideration for the next person. They created order in the midst of overflow. They made beauty out of what could have been an eyesore.
That's a tremendous person.
Tremendous people don't dump their junk everywhere and expect others to deal with it. They care enough about our collective surroundings—our teams, our families, our communities—to handle even life's overflow with intention. They understand that the trash is part of the journey, but it doesn't have to define the landscape.
They make a trash pile look like a work of art.
Who are you surrounding yourself with? People who carelessly toss their baggage into your space? Or people who, even when life overflows, take the time to stack things with care?
Your 2026 Challenge
This year, I challenge you to be the person who neatly stacks the trash. Deal with your stuff. Give it structure. And remember—your hard seasons, your disappointments, your transitions through the tough stuff? They don't have to be ugly.
Make the journey beautiful, even when it's messy.
And for goodness' sake, hang around people who do the same.
Because the trash from 2025? It's still there.
But oh, what a difference positioning makes.
What "trash" are you carrying into 2026 that needs some structure—and some beauty? I'd love to hear from you.
