Fortune Favors the Bold… Or Does It?

“Fortune Favors the Bold.”
Or does it?
Audaces, Fortuna, Iuvat”
A Latin proverb that is also happens to be the motto of my Naval Academy class of 1992.

When I first graduated and became a Marine Corps officer it was these types of inspirational quotes that drove myself and my fellow Marines forward to take decisive action. Often those bold decisions played out well. Other times they failed majestically. What I failed to realize and only came to learn years later is that leadership encompasses dichotomies and not absolutes. The way a leader assesses and makes decisions is through awareness and observing. The opposite dichotomy to boldness is timidity. Many would agree that being timid rarely brings forth the success a leader seeks, but it can also inspire patience to become more situationally aware before taking bold action.
Years ago, when I was working with defectors (spies) that had decided to work with us in the FBI I asked a Russian SVR Colonel what made him such a bold risk taker. He laughed at me, slapped me on my shoulder good naturedly and assured me he was no bold risk taker. He explained how he had been patient, assessing the world, politics, his situation, and his families for many years. He agreed his choice to defect was bold, but not reckless or without patient contemplation and massive situational awareness.

The greatest and most impactful leaders are bold and decisive, but they do not act impulsively or reckless without situational awareness. Learn to balance the dichotomy.