When working with leaders approaching retirement—or any transition into a new phase of life—I often see a subtle but powerful shift in mindset. Where there was commitment to growth and expansion, our dialogues sometimes surface a quite different sense of anticipation: that of quiet decline. It’s understandable. After decades of high performance, the narrative starts to whisper: “Maybe it’s time to wind down.”
Increasing Capacity
Yes, there are changes that happen. I can’t sprint as fast as I used to or pull back-to-back all-nighters. Joints creek.
In my thirties, I had a mentor who taught me about increasing usefulness with age. Which is a very different mentality than the “three score years plus ten, and you’re done” that was the culture I grew up in. He spoke about new capacities coming on line, abilities that, in younger life, we didn’t even know were important, and this has proven to be my experience.
While I see fewer clients than I used to and travel less for meetings, my presence is more deeply felt, I understand people and situations quicker and more completely, and whatever wisdom comes through seems to be more impactful.
Using Limited Time to Focus Priorities
Coming from the idea of limited time has its benefits. One invariably moving exercise I have used in retreats is to give each person seven post-it notes and ask them to write their seven most important priorities. Could be a person, project or experience.
Then we have four rounds of sharing: If you had just 5 years left to live, which two would let go. Then 5 months, 5 days. What would you do with that time? With 5 hours left… there is just one post-it note, one priority remaining. It’s a clarifying way to prioritize what matters most—and reorder or let go of what doesn’t. You may have done something similar.
But then we flip it.
What if you had 100 years left?
With whom would you surround yourself? What will you create? How do you love? Who might you mentor? What legacy would you shape if time were not an issue? This question reframes everything. Instead of managing decline, you begin designing your future through the lens of longevity, usefulness, and lasting impact. It connects you with the full depth of who you are.
This shift isn’t just conceptual. It exposes the very strategy by which you have been living, and recalibrates it. It frees you from self-imposed limits. Opens up a fresh runway—where age brings not irrelevance, but greater value.
Give it a try. You might be surprised how much possibility returns when you stop counting down—and start thinking longer. Let me know what you are discovering about increasing usefulness with age.
Best,
David Lesser