Leadership of a Certain Age: Embracing Chaos, Clarity, and Change
Share
“I’m of a certain age, you see, when life becomes poetic…”
Leadership, like life, evolves. In our early years, we often believe that being a strong leader means being decisive, certain, and always in control. We strive for clarity, for perfection, for a clean line from point A to point B. We fear mistakes, we fear ambiguity, and above all, we fear the messiness that leadership inevitably brings.
But then something shifts.
Maybe it’s age. Maybe it’s experience. Maybe it’s just exhaustion from trying to hold everything so tightly. Either way, we arrive at a new truth: chaos is not the enemy. It’s the medium. It’s the canvas. It’s the storm that carves the shore.
From Fear to Fluidity
"What used to seem the world’s true end, now harmless though frenetic…"
Leaders who’ve been tempered by time start to see crisis differently. Where younger versions of ourselves might have scrambled to control every outcome, the wiser version learns to stand in the storm without losing ground.
The frenzy of missed deadlines, shifting strategies, resignations, reorganizations—it all feels less personal now. Less like a collapse, more like a remix. We recognize that the end of one plan is often the beginning of a better one. Leadership becomes less about mastery and more about movement.
Wisdom Isn’t Clarity—It’s Comfort With Confusion
"Now I don’t mind confusion much because I finally get it…"
There’s a profound kind of leadership that emerges when we stop needing to have all the answers. We trade rigid confidence for curious presence. We listen more. We ask better questions. We tolerate the unknown long enough for new truths to emerge.
Great leaders—of a certain age or not—understand that confusion is not failure. It’s a gateway to creativity. It’s where the most human solutions come from.
Leading Through Chaos
"Chaos makes the world go round, yields beauty if you let it."
Let’s be clear: embracing chaos doesn’t mean becoming passive or careless. It means leading from a place of humility and trust—in your people, your instincts, and the unfolding process. It means trading micromanagement for mentorship. Trading control for clarity of vision.
When leaders stop resisting chaos and instead partner with it, something transformative happens:
- Teams feel safer to try bold ideas
- Innovation increases
- Culture deepens
And perhaps most importantly, the leader herself feels freer—less burdened by the illusion of perfection
Leadership That Ages Well
To lead of a certain age is to recognize that experience is not just measured in years, but in how well we’ve learned to let go. It’s leadership with laugh lines, with stretch marks, with a memory of mistakes turned into momentum.
So whether you’re 35 or 65, maybe the question isn’t how old are you?
Maybe the better question is:
How open are you to letting leadership be poetic?
To seeing beauty in the mess?
To leading with more presence and less performance?
That’s the kind of leadership that truly ages well.
Of A Certain Age
I’m of a certain age, you see, when life becomes poetic
What used to seem the world’s true end, now harmless though frenetic
Now I don’t mind confusion much because I finally get it
Chaos makes the world go round
Yields beauty if you let it