On Leading with Greatness

In some ways, I feel my writing is spinning in place as I age in place, so I’ve decided to take a few months off—at least—as I consider my next move and enjoy my summer. Summertime is the perfect time to take time.

The best artists, like the best leaders, never treat their work as finished. They master their craft, then break it, reworking, searching, risking public failure rather than coasting on what already worked. Let's call that restlessness unsettlement. It's a value leaders and artists share more deeply than any other.

This episode makes the case for it: not repetition, not persistence for its own sake, but the discipline to keep moving toward something not just different but better and the nerve to smash your own best work when there's somewhere else to go.

Bob Dylan, John Coltrane, and Henry Threadgill supply the evidence. The lesson isn't "lead like an artist. The stakes and the processes are worlds apart. It's narrower and harder: be self-aware but not self-satisfied, disciplined in a way that's true to yourself, and willing to build, break, and build anew.

So much information, and so little time to review it, which is to say nothing of comprehending and intelligently responding to it. We drift in a world awash in information, gulping it down as quickly as possible in hopes we don’t drown.

Yet, “leaders are readers,” or so they say. Leaders gain knowledge and a degree of understanding by guzzling information.

What does a person’s behavior suggest about their level of competence?

The most competent among us aren’t hyper-confident and are often riven with self-doubt, which you might not realize if you aren’t close to them or you actually are them. I’m not talking about imposter syndrome. The self-doubt a competent leader experiences is an entirely healthy and even necessary element of their competence.

Most leadership advice suggests that empathy is a key component to effective leadership, and I won’t disagree. Leaders empathize to improve their ability to communicate and to compromise. But…

Empathy is not inherently good. Empathy can be a component of morality, but it’s not moral in itself.

Have you ever considered the inherent value of taking action and getting things done? We sometimes refer to comic book heroes as “action heroes,” but do you think action is heroic in and of itself?

Leaders understand that justice is a key leadership value and that it must expand beyond mere retribution toward a more holistically just future.

Leaders know that silence enhances pain, trauma, and injustice. Silence is the tool of the cruel. Leaders stand tall as its sworn enemy.

The truth is that the player who attempts to bluff always does so from a position of deficiency. You wouldn’t be bluffing if you placed a high bet on, say, a straight or a flush unless you somehow knew for a fact that your opponent held four of a kind. Therefore, bluffing is always a de facto admission of weakness even when the player wins.

Leadership and writing have some direct parallels, not the least of which is that when done well, people don't notice.