I Ching and the Art of Making Shit Up

Radical Experimentation for Weirdos Like You and Me

I’ve never lived life according to a five-year plan. Or a one-year plan. Or even a “what-are-you-doing-next-week?” plan. I live like a Thelonious Monk jazz arraignment—unscored, moody, and sometimes brilliantly off-key.

At my core, I am a nomadic, Taoist-fueled soul, I’m equal parts philosopher, provocateur, freedom seeker, and spiritual hype man with a soft spot for Peet’s coffee and Puma kicks. My life has been one long experiment in trial, error, reinvention, collapse, renewal, and figuring it all out on the fly—usually while sipping tea and decoding the I Ching.

And guess what? It works. Sort of.

See, while the rest of the world obsessively updates resumes and vision boards, I’ve been wandering bookstore aisles, meditating in Qigong poses, dancing at unexpected pop-up art events, and talking metaphysics with strangers in bougie cocktail bars. There is no GPS for a Taoist life. There’s only presence, improvisation, and the willingness to not know.

This isn’t accidental. It’s by design.

Because I believe with every cell of my being that the greatest path forward in life isn’t the one mapped out in advance—it’s the one you co-create by stepping into the unknown with curiosity, reverence, and just enough absurdity to laugh when it all falls apart.

The Tao Is Not a Business Plan

Let me be blunt…. I’m not here to sell you a formula. I’ve tried formulas. They made me miserable.

Life isn’t a funnel. It’s a field. And it’s meant to be wandered, not optimized.

Some of my greatest awakenings happened not during peak moments of success but in the breakdowns—the in-between places where I had to experiment my way through confusion.

Like the time a few years ago I ended up unhoused in San Diego after a breakup. I sat behind a Whole Foods in Hillcrest, dressed in a sport coat and jeans, calling through my contact list in desperation.

One person answered. A stranger I’d met six months earlier at a bar. He and his dog Audrey picked me up, gave me shelter, and unknowingly became a cosmic sign that I was still held, even in chaos.

You don’t plan for that kind of rescue. You fall into it.

Like Hexagram 29 of the I Ching: The Abysmal (Water). It teaches us that repetition—falling in, getting wet, climbing out again—isn’t failure. It’s flow.

The water doesn’t resist the canyon. It becomes the canyon.

The I Ching as a Spiritual GPS (But One That Sends You on Detours)

If you’re unfamiliar with the I Ching, you’re missing out on the most cryptically honest coach you’ll ever meet. Unlike the neat little advice packages you find on TikTok or in corporate keynotes, the I Ching doesn’t give you answers—it gives you movement.

You ask a question, toss your coins (or yarrow sticks if you’re feeling extra), and you get a hexagram—a six-line symbol representing a state of change.

And that’s the punchline: everything is in flux. Always. The job of the I Ching isn’t to tell you what to do, but how to be with what is.

Want to start a business? The I Ching might respond: “Proceed, but only after proper preparation and humility. Also, wait for the right allies to show up.”

Want to fall in love? “Cool. Just remember, clinging leads to sorrow. Be like fire—burn bright, don’t try to own the flame.”

Want clarity?

It might throw in Hexagram 4: Youthful Folly your way, which is its poetic way of saying, “You don’t know what you’re talking about yet. So shut up, observe, and keep learning.”

This is the heartbeat of my life philosophy, namely, learn by doing, stumble forward, adjust on the fly. And somewhere in that dance, you find your rhythm.

What an Experimental Life Actually Looks Like

Here’s what this Taoist, trial-and-error, jazz-souled way of life looks like in real time:

• I start projects without knowing where they’ll lead. Some become essays. Some become interviews. Some become digital campfires for others to gather around and talk about the Tao of gentrification or the philosophy of snow globes.

• I launch offerings before they’re perfect. Pay-what-you-can Taoist coaching journeys? Wisdom salons disguised as Zoom chats? A zine that looks like it was created by a philosopher on a Chicago train with a Sharpie? Yes, and yes.

• I stop waiting for permission. No more gatekeepers, algorithms, or blue checks. I’ve realized I am the platform. I’m not building an audience—I’m broadcasting a frequency. Those who need to tune in, will.

This doesn’t mean it’s all smooth. Sometimes it’s chaos. Sometimes it’s crickets. But each stumble refines the path. Each misfire teaches me what not to do next time.

And honestly, that’s the best MBA I could ask for.

So What Does This Mean for You?

If you’re stuck, if you’re waiting to feel “ready,” or if you’re clinging to someone else’s map—this is your cue to burn the damn thing. Life is not a test. It’s a tuning fork. And your job is to find your pitch by playing a few wrong notes first.

So here’s some Taoist-infused, I Ching-approved, slightly rebellious advice:

💥 Start before you’re ready. Don’t know what you’re doing? Perfect. That means you’re teachable.

💥 Try wild ideas. Host that dinner. Write that essay. Launch that side hustle no one understands.

💥 Fail weird. Make glorious mistakes that leave you laughing, humbled, and strangely proud.

💥 Consult the I Ching. Not for answers, but for better questions.

💥 Let go of outcomes. Measure success by frequency, not likes. By energy, not applause.

Most importantly, remember this: You’re not here to follow the path.You’re here to be the path.

The Boldest Invitation

If you’ve been playing it safe, this is your moment to go feral.

Make a mess. Write a thing. Say yes to something that terrifies you. Let your curiosity lead you—not to perfection, but to discovery.

This is the essence of The Chocolate Taoist.

It’s poetic. It’s profitable. It’s unpredictable.

It’s where your soul finds resonance in a world gone mad.

So walk with me—not because I have the answers, but because I’ve surrendered the need to chase them.

Let’s build lives that hum.

Let’s become frequencies that heal.

Let’s make it all up—as we go.

Ever feel like you’re making it all up as you go? Good. So am I. And spoiler: that’s where the magic is.

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Diamond Michael Scott

aka The Chocolate Taoist