Phil Jackson and Ryan Holiday
Let’s get real—life isn’t a straight line. Rather, I have found that it’s a wild, winding dance of chaos, clarity, and everything in between.
The good news is that often along this unpredictable ride, we stumble upon those rare guides who make us stop, rethink, and step up our game.
I’m not talking about gurus on a mountain or self-help influencers with cheesy catchphrases. I’m referring to true senseis. In Japanese, sensei means “one who has gone before,” but in my world, it’s deeper than that.
A sensei is someone who’s been in the trenches, who’s faced the fire, and who can drop wisdom that shakes you to your core. They’re like human North Stars, helping you navigate the mess without giving you a map.
Unlike a muse, who might light a creative spark, a “sensei” is a guide who gets down in the dirt with you, teaching through action and example.
Two sensei have emerged for me from unexpected places — Phil Jackson, the Zen Master who turned the basketball court into a dojo, and Ryan Holiday, the modern author and Stoic thinker who brings ancient grit to today’s chaotic grind.
Phil Jackson: The Zen Master of the Hardwood
Phil Jackson is the kind of sensei who flips the script on what it means to lead. Dubbed the "Zen Master," he wasn’t just a Hall of Fame basketball coach. He redefined the game.
Jackson brought meditation circles to the NBA, where egos are bigger than the arenas, and taught his players the art of balance—between pushing hard and letting go.
Under his influence, they learned that there’s more to winning than just the score; there’s a rhythm to it, a flow. It’s Taoism in action, the idea of Wu Wei or effortless action—where the most powerful moves come from a place of yielding, stillness, and presence.
Jackson’s approach wasn’t about breaking opponents. It was about breaking down the walls within, clearing the mind, and tapping into something bigger than themselves. That’s why he’s my sensei — he didn’t just teach me how to play. He taught me how to “be” in life.
Ryan Holiday: The Modern Stoic Sage
Then there’s Ryan Holiday, a different breed of sensei but just as potent. This guy takes no prisoners when it comes to mental resilience. He’s the one who’s revived Stoicism for the modern soul, distilling ancient wisdom into tools you can use every damn day.
Holiday teaches that life’s chaos isn’t an excuse, it’s a training ground. His philosophy is like a gut punch to complacency—it challenges you to see obstacles as opportunities and pain as a pathway to growth.
It’s the kind of truth that hits you like cold water, waking you up to the fact that most of what holds you back is all in your head. His work reminds me of Taoist thought, where strength is born from yielding, and power from knowing when to flow and when to stand firm. Holiday’s writings are like a GPS for your soul, guiding you through the noise to find your own path.
Sensei vs. Muse: What’s the Difference?
So, what’s the deal between a sensei and a muse? Think of a muse as a spark—a fleeting moment of inspiration that hits like a lightning bolt. They make you want to create, to move, to do something.
But a sensei? A sensei isn’t here to light you up for a moment; they’re here to transform you. They don’t just inspire—they teach, they challenge, they hold a mirror up to you until you see what’s real.
A muse gets you started, but a sensei keeps you going. A muse might help you write a song; a sensei will make sure you write the whole album, face the critics, and still stay true to yourself.
Finding a Sensei: The Tao of Guidance
Finding a sensei is not like hunting for a mentor on LinkedIn. Rather, it’s about recognizing those who move with a different kind of gravity—those who live their truth in a way that calls you to live yours.
In Taoist thought, a sensei appears when you’re ready, not when you’re searching. They might not be wearing robes or speaking in riddles but are more likely to be coaching a basketball team or writing books on the grit of life.
The key is to stay open, to keep your inner compass tuned to what resonates with your soul, not just what looks good on paper. A sensei doesn’t have to be a master in the traditional sense—they just have to be real, walking the walk they talk.
The Wisdom of Two Sensei
From Phil Jackson, I learned that the real game is internal—if you can’t master yourself, how can you lead others? From Ryan Holiday, I took away that the obstacles aren’t in the way; they are the way.
These two sensei’s—one who was in the high-stakes world of sports, the other in the realm of philosophy—have taught me that wisdom isn’t something you learn — it’s something you live.
So, if you’re looking for a sensei, don’t just look for someone who inspires you. Look for someone who challenges you, who forces you to confront your shadows, who makes you want to grow not just for the applause but for the deeper game of life.
Stay open, stay curious, and let the right guide find you when the time is right. And when they do, take a deep breath and dive in—because that’s where the real journey begins.
Since 2022, I, Diamond Michael Scott, aka The Chocolate Taoist, have delivered uncommon nomadic wisdom to help you live a more interconnected and expansive life.
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