Dear Fellow Travelers,
Welcome back to the Perennial Leadership series, where we’re exploring ancient lessons for modern leaders. Here are the first two volumes: How to Lead Yourself Like Socrates and How to Lead with Simplicity Like Epicurus, in case you missed them.
As a reminder, if you’d like to become a member, there are a few ways to do so: (1) subscribe for $5 a month or $39 a year; (2) use this 50% discount link if you need assistance; and (3) if you can’t afford it, please accept a complimentary membership.
Be wise and be well.
Perennial Leadership
Perennial Leadership is an eight-part series that argues effective leadership emerges from within—not from tactics or titles, but through continuous effort to develop your character, attention, and inner life. Each meditation offers a philosophical insight, illustrated with historical examples and practical exercises designed to introduce ancient lessons for modern lives.
How to Lead by Letting Go (Lao Tzu)
Legend says that Lao Tzu, weary of the noise and ambition of court life, left society behind, riding westward on a water buffalo. At the border, a guard recognized him and begged him to write down his wisdom before he vanished.
Lao Tzu agreed, sat down, and wrote a short book. The Tao Te Ching (or The Way of Virtue) was born—a slim volume that has influenced philosophy, spirituality, and leadership for over two thousand years.
Its central paradox is simple and striking:
What is soft is strong
What is humble is powerful
What is quiet is transformative
Lao Tzu teaches that the world responds better to harmony than to force. A leader who pushes, strains, and clings ultimately exhausts themselves and others. In contrast, a leader who listens, adapts, and lets go naturally earns others’ trust.
1. The Strength of Not Forcing
Wu wei is often translated as “non-action,” but that can be misleading. It doesn’t mean laziness or passivity. It means not forcing—moving with the natural flow of things instead of against it.
Lao Tzu writes:
“The Master does nothing, yet nothing remains undone.”
— Tao Te Ching
This is the paradox: when you stop trying to control everything, more becomes possible. When you loosen your grip, other people step up. When you remove unnecessary pressure, energy can flow where it is needed.
The leader who practices wu wei is not disengaged. They are attentive without being frantic. They watch carefully, listen deeply, and act at the right time.
Instead of constantly intervening, they ask things like:
What wants to happen here?
What direction is this already moving in?
What is the simplest, clearest step that actually helps?
Phil Jackson and the Zen of Leadership
A modern example of wu wei in action is Phil Jackson, the “Zen Master” coach of the Chicago Bulls and Los Angeles Lakers. Jackson led his teams to 11 NBA championships, not by dominating his players, but by cultivating calm, trust, and shared responsibility.
He wrote:
“The most effective way to get players to perform at a high level is to free them from fear.” — Sacred Hoops
