Leave Room for the Unexpected
Photo by Nizar F
One of the things I realized recently is that some of my favorite memories came from plans that didn't work out.
Before a recent trip, I had researched cafés I wanted to visit, activities I wanted to try, and places I didn't want to miss. I enjoy planning, and having an itinerary gives me something to look forward to.
But when I looked back on the trip, I wasn't remembering the plans. I was remembering the unexpected.
A café I found because I decided to take a different road. Staying somewhere a little longer simply because it felt right. A conversation I never expected to have. Even the mishaps—a flooded room on my first night, getting sick, a rescheduled activity, and falling off an electric skateboard—have somehow become the stories I laugh about the most.
Somewhere between making plans and living them, I had forgotten that not everything worthwhile can be scheduled.
It made me wonder: Do I approach work the same way?
When did I start believing that every deviation from the plan meant something had gone wrong?
We spend so much time building project plans, timelines, strategies, and processes—and we should. They give us direction. But somewhere along the way, many of us begin to believe that if something doesn't go according to plan, then something has gone wrong.
A client changes direction.
A meeting takes an unexpected turn.
A proposal comes back with revisions.
A deadline moves.
Instead of seeing these moments as part of the process, we often treat them as interruptions to it. Then it struck me.
Maybe we've confused professionalism with seriousness.
I had a similar thought while reading Project Hail Mary by Andy Weir. What stayed with me wasn't only the science or the impossible challenges. It was the main character, Ryland Grace's mindset. Every solution created another problem. Every plan had to change. Yet instead of becoming overwhelmed by what wasn't working, he remained curious about what might.
He didn't waste time wishing reality matched the original plan. He worked with the reality in front of him. Isn't that what good work asks of us, too?
The teams I've enjoyed working with most weren't the ones where everything went perfectly. They were the ones where someone could admit a mistake without fear, everyone would laugh for a moment, and then immediately ask, "Okay... what do we do next?"
There's a lightness in teams like that.
Have you ever noticed that the teams you enjoy working with most aren't usually the ones with the fewest problems? They're the ones who make even difficult days feel manageable.
Not because they don't care.
Because they trust that together, they'll figure it out.
That kind of culture doesn't ignore responsibility. It simply refuses to let every setback become heavier than it needs to be. It creates space for curiosity instead of blame, perspective instead of panic, and progress instead of perfection.
John Lennon is often credited with saying, "Life is what happens to you while you're busy making other plans." Whether we're travelling, building a business, or leading a team, I think the same idea applies. Some of the most meaningful moments happen in the space between the plan and reality.
Planning gives us direction. But flexibility is often where the best stories—and sometimes the best work—begin.
So perhaps the question isn't: How do we make work more fun?
Maybe it's: How do we stop making every unexpected moment feel so heavy?
Maybe that's what "keeping things fun" really means.
Not making work entertaining.
Not avoiding responsibility.
But leaving enough room for curiosity, perspective, and even laughter so that every unexpected turn doesn't feel like failure.
After all, if some of life's best memories come from the plans that changed...
Why should work be any different?
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Fundamental of the Week #10: KEEP THINGS FUN
Our day-to-day work problems are small compared to those facing most of the world. Laugh every day; don’t take things too seriously.
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