Knowing When It’s Time to Move On
This week, I found myself walking through a building that has been part of my life for more than 26 years. As I looked around, memories came flooding back. I thought about the young woman who started a business from a two-bedroom apartment and couldn’t have imagined where the journey would lead.
I thought about the long days, the celebrations, the lessons, the friendships, and the countless decisions made within those walls.
I thought about my children. Long before they had first jobs, they were spending time in the office with me, being raised in it. There were seasons when I was building a business while raising a family, balancing conference calls and deadlines with snacks, playpens, and little feet running through hallways. They grew up alongside the business in many ways. It wasn’t just where I worked. It was part of their childhood.
I thought about the people, too.Not just employees, but people who became part of our story. People we celebrated with, learned from, laughed with, and spent years walking alongside. After enough years, the lines between coworkers and extended family begin to blur. Shared experiences have a way of doing that.
As I stood there reflecting, I realized I wasn’t thinking about a building. I was thinking about a chapter of life.
For a long time, I thought this chapter was the legacy. Not the building itself, but what it represented.
The business. The years invested. The growth. The life built around it.
But leadership has a way of teaching us lessons we don’t always expect. Sometimes what we believe is the legacy turns out to be the training ground for it.
The building wasn’t the legacy. The company wasn’t the legacy. The legacy is what remains after the season ends. The values our children carry with them. The relationships built over decades. The lessons learned through responsibility. The character formed through hard decisions. The wisdom gained by showing up year after year. And perhaps most importantly, the ability to recognize when a season has given you everything it came to give.
That realization has had me thinking about leadership in a different way. We’re often taught that leadership is about perseverance. About staying committed. About seeing things through. And sometimes it is. But leadership is also about discernment. It’s about knowing the difference between a season that still needs your stewardship and a season that has completed its work. Many people know how to begin. Many know how to endure. Far fewer know how to leave well.
We stay because we’re loyal. We stay because we’re grateful. We stay because we’ve invested years of our lives.We stay because history carries weight. Yet there comes a point when leadership requires us to ask not what we can continue carrying, but what is wisest to carry forward. Because life changes. Priorities change. Families grow. Health matters. New opportunities emerge.
The person you are at 50 is not the person you were at 21, nor should they be. Leadership isn’t just about honoring the commitments that shaped us. It’s also about honoring the people we’ve become because of them.
Sometimes the next right decision creates more space for family. Sometimes it protects your health. Sometimes it opens the door to new work, new impact, or a different way of contributing. Sometimes it simply reflects a deeper understanding of what matters most.
That isn’t quitting. That isn’t failure. That’s stewardship.
A Reflection for You
As you think about your own leadership, I want to leave you with three questions:
What am I holding onto simply because it’s familiar?
What season has given me everything it came to give?
What would I choose if I made my next decision based on wisdom rather than obligation?
Those questions aren’t always easy. But they often reveal where growth is waiting.
This week, as I reflected on 26 years, I wasn’t focused on an ending. I was focused on gratitude. Gratitude for the people. Gratitude for the memories. Gratitude for the lessons. Gratitude for a chapter that shaped my life in ways I am still discovering. And gratitude for the reminder that leadership isn’t about holding on forever.
It’s about stewarding each season well, carrying forward what matters most, and having the courage to step into what comes next.
Lead well,
Mairin Moore Cane