Ryan Holiday knows there’s more to stoicism than its common definition as a synonym for spartan (cold, rigid, brutally harsh). He knows that if it really was just that stereotype, the philosophy wouldn’t have lasted so long. Nor would he be able to write numerous illuminating articles and two best-selling books on it. Which is why it is so disappointing that he could not pay Stoicism's Eastern cousin, Zen Buddhism*, a modicum of the same respect--dismissing it in a few sentences with the straw man stereotype of the monk-recluse alone in his garden on a cliff.
What Ryan does not mention is that feudal Japanese life, like caste-based Indian life or Imperial Chinese life--all lives Zen and Buddhism made better--was anything but a holiday. It was a grueling, hierarchical and wretched existence full of familial obligations and draconian laws. These were the ties that bound people together in a land where resources were scarce and disaster was always a couple of bad harvests and a disgruntled warlord's rebellion away. It would be very easy under such repressive and oppressive regimes for leaders to tyrannize their subjects and engage in needless bloodshed, as many did.
But there was one group of people whom the daimyos and despots not only feared, but who were capable of changing their hearts and slaking their bloodlust: Zen monks. Those gardens weren't celestial pleasure domes where Orientalists like Coleridge might have escaped from reality, but places of meditation where emperors and commoners alike sought advice, gained mental clarity and even sparked creativity, not unlike the bedside of Marcus Aurelius or the olive tree under which Socrates and his friends sat.
Warriors. Peasants. Merchants. Poets. Governors, shoguns, even matrons and prostitutes were all practitioners. Stoicism may have been for men of all professions, but Zen really was for everyone.
But I'm not blaming Ryan. It's easy for us in this productivity-obsessed age to dismiss the seemingly frivolous, pointless simplicity of Zen. Just as the gilded potentates of ancient Asia dismissed the austere and stoic Romans. But that would be a mistake. For in both cases simplicity heightened effectiveness, and in Zen's case frivolity was the point. It made digestible a much more expansive view of the world; one that realized that peasants, princesses and even emperors suffered and that paradoxically the key to the most serious business of all--saving souls--lay in being okay with our reality, and even having fun with it.
Zen is disciplined play.
It's a discipline that helps you approach big problems with the lightness of being that you would have if your life were a game. Get good enough at zazen and you could even unlock "enlightenment". A state of mind that's virtually impossible to describe, although you can get close with psychedelics. You may catch a glimpse immediately after you crack one of those silly lateral thinking problems, ride the Mavericks wave, or 'get' a really funny joke. Only it lasts longer because the eureka is on a much more profound level, what Mihaly Csikszentmihalyi and Steven Kotler describe as the most intense level of flow. It will also make you a better person by the simple fact that 'oneness' is impossible without empathy and compassion. And the best part about it is you can get there without paying a dime--just be still.
Like Stoic philosophers, Zen teachers understood that most suffering is self-imposed, but Zen teachers also realized that you can't convince somebody to lighten up without first making them experience lightness. Deep change requires cognitive dissonance. Just as you can brainwash someone into servitude, you can also mindfuck them into freedom. It's why the greatest Zen masters were also phenomenal practical jokers. Or why it's not uncommon for students who finally 'get' a koan they've been puzzling over for weeks or even years to burst into laughter.
It's no wonder people from all walks of life wanted Zen wisdom. Zen made life fun.
Contrast this with Stoicism's most avid follower, Cato, who never laughed, was viewed as a bore even by his closest friends, and failed to change the mind of his greatest enemy, Caesar. Cato's own inner turmoil led him to literally tear his insides out when the world didn’t go his way. Can such a man truly be said to have mastered himself in the face of life's vicissitudes? I'm not going to speculate on whether the Roman republic might have survived had Cato been better company. But you don't have to live in a society like Japan's, where people agonize for weeks over the precise way to phrase a request for help, to see that we could all use some profound cosmic humor.
Socrates became the wisest philosopher in the Western world because he alone was open-minded enough to admit that he knew nothing. Similarly, Zen teachers will tell you they have nothing to teach. But that doesn't mean we have nothing to learn. Which is why, on the subject of Zen, a practice that has helped millions find long life and success no matter how harsh or repressed their surroundings, Ryan Holiday would do well to follow their example.
*I’m far from an expert. So for a good intro to Zen, check http://www.zen-buddhism.net/ and pick up Zen Mind, Beginner’s Mind. For an explanation of Zen that makes sense within our modern context, look for Alan Watts’ Zen videos on Youtube and his book, The Way of Zen.