Memorial Day Weekend provides us all with an opportunity to remember the lost leaders of the past and hopefully gain some overdue leisure time.
Leadership and leisure are surprisingly related.
Please enjoy the most remarkable reading, watching, and listening I’ve encountered on these topics.
“Long Weekends and Leadership”
[7 minute read]
“This is the main question, with what activity one’s leisure is filled.”- Aristotle
When you hear “great leader” who do you think of? Someone who “leads by example” sounds like the right gut response. In terms of discipline and commitment, I always think of gravel-voiced former Navy SEAL Jocko Willink. Amusingly, he tweets a picture of his wristwatch every day at 4:30 a.m. before his workout. His mantra is “discipline equals freedom.”
It’s not for everyone, but it really seems like Willink embodies his own philosophy. David Foster Wallace tried to articulate the mysterious quality possessed by genuine leaders.
“If you’ve ever spent time in the military, you know how incredibly easy it is to tell which of your superiors are real leaders and which aren’t, and how little rank has to do with it. A leader’s real “authority” is a power you voluntarily give him, and you grant him this authority not with resentment or resignation but happily; it feels right. Deep down, you almost always like how a real leader makes you feel, the way you find yourself working harder and pushing yourself and thinking in ways you couldn’t ever get to on your own.”
A resonant phrase I heard recently that really stuck with me was: “you can’t bring through what you haven’t lived.” We can intuitively detect hypocrisy. Chinese philosophy scholar and professor of embodied cognition Edward Slingerland’s book Trying Not to Try discusses the Taoist concept of “de.” This is a kind of charisma emanated by people who are acting in effortless harmony with the world around them. Slingerland thinks we are drawn to these people because we have evolved to detect subtle signs of insincerity; of talking the talk without walking the walk.
Why does the cowboy hero win when the villain always draws first? By drawing first, the villain has to act consciously, the good guy reacts to him unconsciously. Unconscious reactions tend to be faster. Funnily enough, physicist Niels Bohr practiced this with his students using toy guys. He won every time, despite drawing second.
Lying takes conscious effort and is often betrayed by unconscious signals, hence the development of polygraph tests. Polygraphs can be fooled with conscious training, but we still cannot lie unconsciously.
Genuine sincerity results from a deeper, embodied manifestation of our own nature. And this is where the importance of “leisure” comes in.
Leisure and leadership seem like awkward bedfellows. Our culture has fetishized diligence and activity as the apotheosis of Western virtue. The utterly exhausting “morning routine of the billionaire” has become a clichéd genre entirely of its own. It always strikes me as mistakenly copying someone else in hope of replicating their unique path to success.
Josef Pieper’s book Leisure, The Basis of Culture explains this concept in some detail. Leisure in this case doesn’t mean idleness or a piña-colada-soaked vacation, it means something a little more profound. Pieper describes leisure as “a form of that stillness that is necessary preparation for accepting reality.” Essentially- a man who can truly put himself at leisure is in harmony with himself and everything around him. This essential nature can be detected by others. Slingerland encapsulates the conclusions of the great Taoist sages:
“All of these thinkers tell us that, if we can just get into a state of complete spontaneity and unselfconsciousness, everything else will work out. We will be in harmony with Heaven. We will possess de, a charismatic power that brings social and political success, and we’ll move through the physical world with supernatural ease.”
William Deresiewicz wrote one of the defining speeches on leadership, delivered at the United States Military Academy at West Point in 2009. For Deresiewicz, the key to leadership is concentration:
“You can just as easily consider this lecture to be about concentration as about solitude. Think about what the word means. It means gathering yourself together into a single point rather than letting yourself be dispersed everywhere into a cloud of electronic and social input.”
We are all so continuously distracted by external e-mail alerts and notifications that we lose track of our own internal conscience and guidance. Deresiewicz describes the moment in Joseph Conrad’s Heart of Darkness where the protagonist Marlow encounters the unsettling, faceless bureaucrat. The man who has nothing left inside of him; he has completely given himself over to the machine. He is no longer himself. Instead, it is concentration on the solitary work of fixing his boat that saves Marlow.
Deresiewicz argues that the link between concentration, solitude, and leadership is that times of incredibly difficult decision-making, we are often our most alone. In those moments, only profound self-knowledge allows us to make the right decision. A moment of conscience that allows for the kind of virtue and harmony that the Taoists describe. You can achieve that through Pieper’s definition of leisure:
“Leisure is not justified in making the functionary as “trouble-free” in operation as possible, with minimum “downtime,” but rather in keeping the functionary human … and this means that the human being does not disappear into the parceled-out world of his limited work-a-day function, but instead remains capable of taking in the world as a whole, and thereby to realize himself as a being who is oriented toward the whole of existence.”
Related reading, listening and watching.
- Watch: The Fallen of World War II by Neil Halloran (18 minute video).
- Why Watch. This is probably my favorite video on the internet. I watch it at least once a year, either on U.S. Memorial Day or U.K. Remembrance Day. Nothing I’ve ever seen has dispassionately visualized the almost incomprehensibly appalling loss of life in World War II. The section on the Soviets made me surprisingly emotional. A powerful educational video to show teenagers or older kids.
- Read: “Leisure, the Basis of Culture: An Obscure German Philosopher’s Timely 1948 Manifesto for Reclaiming Our Human Dignity in a Culture of Workaholism”- by Maria Popova (18 minute read).
- Why Read. I believe Popova’s Brain Pickings is one of the highest ROI sites out there, and this is an amazing piece synthesizing today’s themes.
- Read: “Solitude and Leadership” by William Deresiewicz (45 minute read).
- Why Read: I first found this article as a response to the question “what’s the best thing you’ve read online that’s over 5 years old.” And it is indeed an awesome speech.
- Listen: Hardcore History by Dan Carlin (Looooong podcast series)
- Why Listen: This podcast series is marathon-length episodes narrated by Dan Carlin, the only man alive with a more masculine voice than Jocko Willink. These podcasts are for real history nerds. The most famous series is about World War One- “Blueprint for Armageddon.” It introduced me to battles I’d never even heard of before but were staggeringly costly, like Operation Michael or the Brusilov Offensive. The latter produced an estimated 2.3 million casualties.
Have a great, leisurely, long weekend.