All good things do come to an end . . . including all executive leadership roles. This post takes readers behind the curtain to understand the complexities and dynamics and benefits of engineering a great ending. Michael Le Roy Associates and MyNextSeason work in partnership to plan and support boards and presidents who want to finish well.

We do not offer nearly enough blessings to one another as we go about our hurried days. Blessings can be a prayer, but they are also affirmations, encouragements, and expressions of hope that we may delight in your good fortune. . . Today, I am thinking about leaders that are taking on new roles as well as those who have been serving in leadership roles for many years. May John O’Donahue’s blessing “For a Leader” be a blessing to you this day.

As I moved into leadership roles and started working with people making big decisions about “retirement,” I realized I was making some significant, erroneous assumptions about the meaning of this concept. As an early and mid-career professional, I understood retirement as “the act of leaving one’s job and ceasing participation in the workforce.” Without examining my assumptions, I imagined retirees as people with almost unlimited discretionary time, low golf handicaps, and time to work through a great reading list in sunny places while the rest of us worked through the winter. But just as the red maple leaf is not nature’s only harbinger of Fall, retreat from the workforce describes only one aspect among many possibilities.

In 2018, six years into a college presidency and thirteen years into my work as a senior leader in higher education, I took a long walk. I walked out my front door and then seven miles to the airport in Grand Rapids with my backpack on, my phone turned off, and the hope that I could walk 542 miles from the French-Spanish border to the Atlantic Ocean.