This is a talk from October, 2009 at the US Military academy by William Deresiewicz. Highly recommend the original transcript over the notes below.

Deresiewicz, William. “Solitude and Leadership: If you want others to follow, learn to be alone with your thoughts.” The American Scholar 79, no. 2 (2010): 20-31. See https://theamericanscholar.org/solitude-and-leadership/↗

Motivation

If you want others to follow, learn to be alone with your thoughts.

Leadership appears to be a busy endeavour. E.g. Abraham Lincoln surrounded by the admirers and people who follow him. Purpose of a military school is to teach leadership, e.g. on the lines of commanding a platoon.

Solitude on the other hand is rare. We rarely spend time on our own. For a generation that doesn’t have the liberty to be physically alone (privacy), solitude, i.e., being alone with thoughts is even rarer.

Solitude is a necessity of leadership. Let’s learn why.

Not leadership

Does being a leader, I wondered, just mean being accomplished, being successful? Does getting straight A[s] make you a leader? I didn’t think so. Great heart surgeons or great novelists or great shortstops may be terrific at what they do, but that doesn’t mean they’re leaders.

Leadership is often incorrectly associated with aptitude, excellence, or achievements. Excellence or achievements are primarily related to setting a goal and doing whatever it takes to achieve them. Education teaches us the later. Often achievement is seen as making it to the top of whatever hierarchy (or bureaucracy) we care about.

This snake ladder game and conflating our love for power with leadership is a mistake. There are two interesting observations.

Why is it so often that the best people are stuck in the middle and the people who are running things - the leaders - are the mediocrities? Because excellence isn’t usually what gets you up the greasy pole. What gets you up is a talent for maneuvering.

Second, what are the behaviors a bureaucracy rewards?

Getting along by going along. Being whatever other people want you to be, so that it finally comes to seem that, like the manager of the Central Station, you have nothing inside you at all. Not taking stupid risks like trying to change how things are done or question why they’re done.

Unfortunately, our focus is training the next generation to keep the routine going. This is a crisis because all we have are people…

Who can answer questions, but don’t know how to ask them. Who can fulfill goals, but don’t know how to set them. Who think about how to get things done, but not whether they’re worth doing in the first place.

The challenge

What we don’t have, in other words, are thinkers. People who can think for themselves. People who can formulate a new direction: for the country, for a corporation or a college, for the Army - a new way of doing things, a new way of looking at things. People, in other words, with vision.

This is the secret sauce, a vision. It is not possible to walk this path by being a conformist, lost in the crowd who have already been bought in to the status quo. We must be able to think independently, creatively and flexibly. Apply these skills to ambiguous situations, and walk the paths never taken before.

There is another necessary ingredient.

No, what makes him a thinker - and a leader - is precisely that he is able to think things through for himself. And because he can, he has the confidence, the courage, to argue for his ideas even when they aren’t popular. Even when they don’t please his superiors. Courage: there is physical courage, which you all possess in abundance, and then there is another kind of courage, moral courage, the courage to stand up for what you believe.

Leadership is being able to think for yourself and the courage to act on your convictions.

Not thinking

How do you learn to think? Well, here’s how you don’t.

Do not multitask. Thinking requires singular concentration on one idea. Spreading yourself thin with attention dispersed through various contexts is the exact opposite of our path.

Distractions take your focus away from the questions worth pondering (the dilemmas). E.g. am I doing the right thing with my life? Am I happy etc. Answers to the worthy questions are rarely external.

Thinking is developing an idea about a topic.

I find for myself that my first thought is never my best thought. My first thought is always someone else’s; it’s always what I’ve already heard about the subject, always the conventional wisdom. It’s only by concentrating, sticking to the question, being patient, letting all the parts of my mind come into play, that I arrive at an original idea. By giving my brain a chance to make associations, draw connections, take me by surprise.

Sticking to one question, being one with one idea, to the exclusion of everything else. This is Solitude.

Finding yourself

”Your own reality - for yourself, not for others.” Thinking for yourself means finding yourself, finding your own reality.

But we get lost in the external.

you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. You are creating a cacophony in which it is impossible to hear your own voice, whether it’s yourself you’re thinking about or anything else.

How to practice Solitude? Introspection, deep concentration, active reading and friendship. Deresiewicz draws a parallel of talking with yourself i.e. introspection with an intimate conversation with another. Later leads you to discover yourself through articulating ideas in a long deep conversations.

Connecting the dots

A leader must find answers to the outstanding dilemmas. These are deep questions that are barely answered by the conversations on the surface, e.g. twitter, the facebook feed or the newspaper. Finding an answer requires vision, new ways of doing things. A vision must be equally matched with enormous courage and conviction to stand up for your ideas.

Developing such clarity requires focus, concentration and patience to dwell upon the intricacies to nurture an idea. Books are your friend. They’re timeless reflection of someone’s solitude. Articulation, in the form of long conversations or thinking out loud, also helps generate clarity.

You must be ready for the moment of crisis where all of us need you. You must make the decisions, alone. Time to prepare for these is now.

Solitude is the essence of leadership.