Dr. Andy Szeto: Leadership After the Title
- 5 hours ago
- 4 min read
After dinner, we made a second stop for coffee at 7th Avenue Donuts & Diner in Park Slope, Brooklyn, a neighborhood institution known for its fresh, handmade donuts. It was late on a Thursday evening, the eve of my new friend’s final day at work. By the time we left the diner, he would be only hours away from retirement after a distinctive career in district leadership and a lifetime of service to some of the most marginalized students in our school system.
I was fascinated by the story of how his career began, in part because it almost did not happen at all. What followed was decades of work shaped by persistence, purpose, and a deep commitment to students too often overlooked by the system. At one point, he described himself as boring. He was far from it. The evening offered a fascinating look back at the life he had built and ahead to a future filled with possibilities.
We had already spent hours talking over dinner, but neither of us seemed ready for the evening to end. Our discussion went far beyond retirement or leadership. We talked about health, family, identity, the passage of time, and the choices that come with a major life change. Because we both work in district leadership, however, I kept returning to one question: what happens to leadership when the title is gone?
He spoke candidly about the freedom that was now close enough to feel real. His first plan was to travel back to his homeland, where he could reconnect with people and places that had long been part of his story. Beyond that, the details were less settled. We talked about activities he might pursue, lessons he might take, and ways he could use the time that would soon belong more fully to him. He also planned to continue teaching part time. He was ready to leave the daily demands of full-time district leadership, but not necessarily the parts of his professional life that still gave him meaning.
Throughout the evening, he jokingly called me “the kid” a few times. We laughed, but the comment also captured the difference in where we were in our careers. At the same time, we shared more than I had expected. We both came to this country as immigrants, began from relatively humble circumstances, built careers through hard work, and found another avenue for service through college teaching. Our paths were not the same, but there was enough common ground for his transition to feel unexpectedly personal.
At one point, he looked at me and asked, “What are you thinking?”
“I’m thinking about my own future,” I said. “In some ways, it feels like I’m looking at myself a few years from now.”
Of course, “a few years” was not quite accurate. Retirement is still at least a decade away for me, and I have little wisdom to offer about that stage of life. What the evening gave me was something different. It pushed me to look further ahead than I normally do and to consider how much of my identity has become intertwined with my professional roles.
Across the different work I do, I mostly enjoy my professional life, even though I would not pretend to enjoy every part of it. There are schools to support, students to serve, courses to teach, articles to write, and ideas taking shape. Retirement still feels distant, but the questions raised that night no longer do.
I have written before about leadership without a title and leadership before one. I have often argued that it is not confined to a position, an office, or an organizational chart. That evening, however, I found myself considering another dimension of the idea: leadership after the title.
It is easy to say that a title does not define us while we still have one. I do not yet know what it feels like when the role is actually gone. I can only wonder which parts remain, which parts we are relieved to leave behind, and whether the sense of purpose built over a career can take on a different form.
My friend’s plans offered one possibility. He would travel, explore interests that full-time work had left little room for, and continue teaching part time. The position would end, but the habits of service, mentorship, and advocacy developed over decades would not simply disappear.
That may be what I found most compelling. Throughout his career, he had devoted himself to students who were often overlooked or underserved. Retirement would close one chapter, but it would not erase the person he had become through that work. The title might fall away, yet the values behind it could remain.
Perhaps that is what unsettled me. A professional role does more than describe what we do. Over time, it can shape how others see us and how we understand ourselves. When that structure is removed, the question is not simply how we will fill our days. It is what remains when the meetings, deadlines, authority, and recognition are no longer there.
I am not offering an answer. This is not a retirement lesson or a set of recommendations. It is a reckoning prompted by sitting across from someone about to enter a chapter that still feels distant to me.
When we left the diner, he was only hours away from his final day in district leadership. Mine remains years away. I did not leave with a retirement plan or a philosophy about what comes next. I left with a question that I suspect will not easily fade: when the title is finally gone, what part of the leader remains?
Lead Forward is an exclusive feature by Dr. Andy Szeto on The Worthy Educator. Check back regularly for new insights for aspiring leaders!
