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The Strange Solitude of Leadership

Most of the men who come to Man-UP! Life Coaching are either in positions of leadership or are aspiring leaders: business owners, corporate managers, creatives, family men, and more. While I was training to be a coach I observed that society has, in some ways, a backward understanding of leadership.

Consider the fourth quarter of a playoff football game. In such a high pressure situation, it is common to hear an announcer say something like: “This is where leaders are made,” or “This is where minds are tested.” But the announcers are wrong. The fourth quarter of a playoff game is where leaders are observed, not where leaders are made or tested.

Sun Tzu famously notes in The Art of War, “Every battle is won or lost before it is ever fought.” A subtle truth of leadership is that it begins–and is tested–in moments of solitude. Paradoxically, leadership is a solitary endeavor. Leaders might speak in front of an audience of people, yet it is “lonely at the top.” Why is that?

One reason, perhaps, is that leadership of a healthy organization requires competence. Continuing our football analogy, the captain of an American high school football team is, nine times out of ten, the team’s best athlete. And to be “the best” is, by definition, also to be alone.

What of that tenth team, though? The team on which some young man has such a curious set of “intangibles” that his teammates vote, “We know he’s not very strong or fast… but he’s our captain.” The loneliness that guy feels is captured in my use of the word “intangibles.”

People who are interested in bearing the burden of leadership are rare. People who are capable of competent leadership are rare. And people who understand the strange solitude of leadership are rare.

One of the privileges of being a coach is being able to observe a group of immensely talented individuals wrestle with their solitary moments in the dark. It is enlightening to watch a client reach the resolution of some internal conflict or reframe the problem before him. By my account, those are the moments when leaders are made.

If you’re still reading this, you are probably finding yourself represented in my words. Perhaps you are looking for a trusted partner who understands your peculiar burden. Or you might be somewhere on the ladder of competence, wondering what it’s going to take to climb to the next rung. Or, you’re finding yourself in pitch blackness and would like to borrow our flashlight. In any case, I’m glad you’re here.


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