The Excited Stoic

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Derek Wyatt is one of my mentors/motivators when it comes to doing business things. A while back, when I was really struggling for motivation and perspective, he suggested a few books that I could read. I didn’t have to read them all, just the ones that I thought spoke to the problem I was having.

So I read two: The War of Art and The Obstacle is the Way. And after enough bus commutes to read both of them, he asked me what I thought.

My opinion, then and now, is that The War of Art felt too aggressive, too militant. (Big surprise, with that title.) Its thesis, as I interpreted it, was that resistance to creativity and creation needed to be confronted head-on, battled in an aggressive and constant war, and with enough pushing it could be defeated, laid to waste.

The Obstacle is the Way, I liked. Its thesis, as I interpreted it, was that trouble was going to happen no matter what, and so battling it head-on is futile and ineffective compared to allowing it to roll over and past you, embracing the chaos and turning life’s slings and arrows into opportunities to do something you never expected.


Many of the talks at XOXO this year incorporated surprise. Not surprising the audience, though that happened from time to time, but the surprises that the speakers had experienced through their careers. Surprise that people could change technology in support of one of its champions. Surprise that a lark of a project could distract someone into a new career. Surprise at the number of people who were so enthusiastic about reinventing comic erotica. Surprise that a life so near its end could be saved.

Many of the talks also incorporated chaos; from the shapeless toxicity of online harassment to the everyday uncontrollability of life itself. And the message, echoed over and over, was that chaos is… well, chaos. It can’t be managed. It can’t be directed. It can’t be fought. So let’s accept it, embrace it, and work with it.

At this point I’m largely repeating Buster’s post. There’s this shift, as we both interpret it, away from getting rid of challenges and roadblocks and towards managing them. We know that the bad is unavoidable, no matter what algorithms try to do for us. We’ve seen how aggravating and ineffectual helicopter parents are. It’s not yet the mainstream, but stoicism is growing.


Since reading The Obstacle is the Way, I’ve been fairly bought in to the idea of Stoicism, the philosophy it espouses. I like spreading it when it makes sense to; partly because I can accurately refer to it as “the ancient art of not giving a fuck”, but also because I think it’s a legitimately helpful way to approach life. And the more I talk about it, the more I remind myself about it, the more it pushes me to apply the ideas to what I’m going through. Sometimes you have to create your own positive feedback loop.

I appreciate that stoicism, unlike mindfulness and meditation, isn’t quite bogged down with any cynical “new age” baggage — baggage that doesn’t exist much in my corners of the world, but baggage that I know exists elsewhere. Maybe stoicism carries the same baggage, but I’ve never seen it. Instead, the image I know about it is more of beardy academics and long-gone civilizations. It’s something Aristotle did, not something I would do. If anything, it’s stuffy.

And so I was immensely pleased to see Nicky Case deliver the heart of the philosophy with such energy. To see Mallory Ortberg give it such comedy. To see Kathy Sierra give it such practicality. To see Eric Meyer give it such heart, and Amit Gupta such hope.

I don’t know that any of them consider themselves stoics, or even know the philosophy exists. All I know is that the speakers, and so much of the audience, seemed to appreciate the ideas that were there. They weren’t stuffy or pretentious (though many were beardy; it is Portland). They were excited by what they heard: that chaos, tragedy, and obstacles may be bad or even horrifying, but the way forward isn’t getting rid of them. Because that’s not possible. Adapting, redirecting, and overcoming… that is.

XOXO illustrations by Brendan Monroe

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