I love those unexpected moments of wisdom that come from random conversations with people you have seen many times but never had an opportunity to speak with them. There is so much to learn if we simply slow down and listen to how others have navigated the stories of their lives.

Recently, I found myself talking with an employee at a well-known resort who has worked there for more than 35 years. As we talked about leadership, organizations, and people, she offered a perspective shaped by decades of experience.

“It doesn’t matter whether it’s corporate America, a nonprofit, a for-profit business, a large organization, or a small one,” she said. “They’re all the same.”

She described organizations as one giant chessboard. There is always a king. There is always a queen. There are people with different levels of influence and responsibility. And there are plenty of pawns. A life of success, she explained, comes from understanding the board. 

Then she delivered the line that has stayed with me:

“The secret to a long and happy career is knowing when to be still and when to move.”

These are simple, blunt, and memorable words of wisdom. 

The more I think about it, the less I hear it as a call to stay silent and the more I hear it as a lesson in awareness. This is knowing when and where to move based on what is happening around you. This looks like reading the room and understanding the board, while recognizing which moments require action, which require patience, and which require an intentional pause.

There is wisdom in knowing that not every battle needs to be fought, not every opinion needs to be shared, and not every hill is worth dying on.

After all, on a chessboard, the most successful players are not always the ones who move the most. They are the ones who understand the board well enough to know when a move matters.

If we pause to listen, these are the moments of learning that can stick with us the longest and have deep impact. 

As I walked away, what struck me most was that she shared her insights with joy, humility, and gratitude. This was not from a place of anger or frustration, but from a genuine appreciation for the lessons she has learned along the way.

Today, and every day, how can we pause long enough to truly listen to the wisdom of others?

A Lesson on Leadership from Raccoons