Rudyard Kipling, in If (1910), offers one of the most quoted and quietly demanding tests of character: “If you can meet with Triumph and Disaster / And treat those two impostors just the same.” It sounds noble, even simple. In reality, it is anything but. Leadership teaches you that emotional balance is not a personality trait but instead it is a discipline, learned painfully, moment by moment.
I was reminded of this recently while attending a funeral of a family member in support of a colleague. Funerals are places of vulnerability, stripped of hierarchy, titles and performance. They ask only presence and humanity. Outside, I encountered a former colleague. Professionally and personally, I had always treated him with kindness and support. He greeted me warmly, enough that a current colleague beside me would have assumed all was well.
And then came the side swipe. Unexpected, pointed, performative. Delivered publicly, quietly, but with intent. Not loud enough to provoke a scene but sharp enough to land. Anyone who has led for long enough knows the moment, the split second when instinct offers rebuttal, defensiveness, correction, or the tempting satisfaction of a verbal counter‑punch.
Instead, I thought of Michelle Obama’s simple and demanding mantra: when they go low, we go high. I smiled, wished him well, and walked away.
It was absolutely the right thing to do. It aligned with my values, my integrity, and the leader I choose to be. And yet, as I walked away, there it was: the sting. The heaviness. The quiet ache that comes not from the insult itself, but from absorbing it in silence.
That is when I remembered the title of my yet‑to‑be‑written leadership book: The Pain of Leadership. It is unlikely to fly off the shelves of Waterstones or any independent bookstore I imagine! It lacks sparkle. But it tells the truth.
Leadership pain rarely looks dramatic. It is not the obvious things like inspection, school budget balancing or constant public accountability. Rather, it is the cumulative weight of moments like this: this injustice when you offered genuine care and support, when eaten bread is completely forgotten and you choose restraint when retaliation would be easier; dignity when ego wants airtime; long‑term character over short‑term satisfaction.
Kipling calls Triumph and Disaster “impostors” for a reason. Both lie to us. Triumph whispers that we are untouchable; Disaster tells us we are diminished. Leadership maturity comes from refusing both narratives. Neither applause nor provocation should dictate who we become.
Walking away that day did not mean the moment didn’t matter. It did. But leadership is understanding that not every blow deserves a response, and not every truth needs defending in the moment. Sometimes the most powerful statement is composure. Sometimes the bravest act is silence. And as native American writer Leonard Peltier writes, ‘Silence is a message. Silence screams.’
The pain of leadership lies in this paradox: doing the right thing does not always feel good, immediately. But it does something far more important. It allows you to keep walking forward without dragging bitterness behind you.
And perhaps that is what Kipling was really teaching us. Not indifference, but mastery. The steady courage to meet both triumph and disaster – and to remain yourself when either one tries to test you. Leadership inevitably brings its own pain. I suspect most often, when the leader genuinely cares.


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