The Courage of Despair

Leadership calls for making tough choices. They’re often unpalatable; this is part of what makes them tough. People dislike change, especially when it requires trading predictable (even if less than ideal) outcomes for the unknown. But sometimes progress calls for a bold leap forward, regardless of how terrifying it seems. What to do?

In The Art of War (5th century B.C.), Sun Tzu wrote:

When you surround an army, leave an outlet free. This does not mean that the enemy is to be allowed to escape. The object is to make him believe that there is a road to safety, and thus prevent his fighting with the courage of despair.

The courage of despair. Archetypical image: Cortés’s ships burning off the coast of Veracruz; his men’s choices reduced to pushing into the unfamiliar or dying alone, marooned. A powerful situation that instigates coherent action; not a hectic, desperate flailing, but a single-minded drive towards a particular direction.

A tricky move to pull off. Cortés’s men probably hated him after he eliminated their path back to “safety.” How do you get people to continue following you after such a gesture? You craft a new identity. No longer a group of rag-tag mercenaries with disparate aims; we’re now a tribe hell-bent on survival. (Again, Sun Tzu: “When I let go of what I am, I become what I might be.”) For this to work, everyone must be committed to the new path — the leader included. After his order was carried out, Cortés, too, was stranded.

I’ve most often experienced the courage of despair in its opposite: the irresoluteness of confidence. A formerly successful team continues operating as before, even when their context has changed radically. Instead of facing the facts and starting in a bold new direction, the leader hedges his or her bets. Unable to grasp — and act on — the urgency of the situation, the team continues in “business-as-usual” mode; their options gradually whittle away; their former cash cows become emaciated. When the moment of reckoning arrives, they’re unprepared. Catastrophe ensues. (I’m ashamed to admit: I’ve been the waffling leader.)

There’s no fighting “as if” your life depended on it. It either does, or it doesn’t. In today’s world, most leaders will not be called on to turn choices into literal life-or-death scenarios. But fostering courage and action will sometimes call for closing off comfortable choices in favor of moving towards new, unfamiliar directions.