Subscribe now

On the surface, the ensō is just a circle. But despite its simplicity, it’s one of the most enduring symbols in Zen Buddhism… which is saying a lot since Zen is a tradition built almost entirely on metaphor and symbolism.

Zen uses symbolism to point toward reality — rather than trying to explain it directly. The idea is to set up the conditions for direct experience, which is the kind of experience you gain only from seeing something for yourself — not from being told something.

It’s that “aha!” moment that appears suddenly and unexplainably.

A useful way to think about Zen symbolism is to think of a map. A map can guide you somewhere, but it is not the place itself.

There are a ton of examples of this in Zen — like the finger pointing at the moon, the sound of one hand clapping, or an empty cup. These are all symbols/metaphors that guide the student to some kind of realization without actually trying to explain the thing itself.

The ensō is one of the purest examples of this approach. A single circle, drawn in a single stroke — and somehow one of the most enduring symbols in all of Zen.

So it’s a little hypocritical of me to try to explain it. But I’m going to anyway, for two reasons.

1. Explanation only goes so far. Even the best description of the ensō stays on the surface. The real meaning only arrives when you feel it for yourself.

2. I’m in good company. Some of the most influential Zen masters of the past few centuries have done the same thing — explained the ensō, at least in part. I’ll borrow from their teachings here.

Here are three classic interpretations. I invite you to consider them lightly — and then go draw some circles for yourself.

1. Enlightenment (Satori)

The ensō is often seen as a direct expression of enlightenment — not as an idea, but as a moment.

It’s drawn in one stroke, without correction or revision. There’s no time to think, adjust, or improve it. It just happens.

What shows up on the page when you paint an ensō is immediate and unfiltered — it’s a reflection of your state in that exact moment of time.

In this way, the ensō isn’t something you perfect. It’s something you reveal. It was always there, just waiting to be expressed on the paper. This revelation is much like the experience of enlightenment according to Zen Buddhism.

Enlightenment, in Zen, isn’t a destination you travel to. It’s not something you earn, build, or achieve. It’s already here — obscured only by the effort of looking for it.

Zen masters like Hakuin Ekaku leaned into this concept by painting bold, imperfect circles and pairing them with questions like: “What is this?” or “Is this a rice cake? The moon? A monk’s bald head?”

The point isn’t to actually answer the question — there is no answer. The point is to catch the mind as it reaches for one anyway.

2. Nothingness (Mu)

Sengai Gibon (1750–1837) was a Rinzai Zen monk who used painting and calligraphy as his primary teaching method.

D.T. Suzuki interpreted Sengai’s circles in his book Sengai: The Zen of Ink and Paper, reading them as “figures of formlessness and infinity.”

Sengai’s ensō pointed toward emptiness — not “nothing” in the usual sense, but the absence of separation.

In Zen, that boundary is seen as something we impose — a way of organizing experience. An expression of duality. That division only exists the moment the line is drawn. Without it, there is just space.

The ensō expresses both at once — the emergence of form, and the emptiness it arises from.

3. Naturalness (Shizen)

Shizen is a Japanese word that translates as “naturalness,” but the meaning is closer to something like “self-so” — that which arises on its own.

It’s the way a child acts, spontaneously and without self-consciousness, before they grow old enough to become performative in their action.

When a child dances, they just dance — there is no performance and no expectations.

Over time, we lose this natural spontaneity. We begin to perform for ourselves and for others. We adjust our behavior around expectations, feedback, and the need to get things right. Our action becomes less “self-so.”

The ensō is a way back. A meditation on spontaneous action.

The rules of the form make this possible. The ensō is drawn in one stroke, quickly, with no correction and no second attempt. There is no time to plan, no opportunity to adjust, no chance to revise. Whatever appears on the paper is what arose — unfiltered and self-so.

Masters like Kazuaki Tanahashi, have practiced this for decades. Each circle is a fresh return to the unselfconscious act and a return to childlike spontaneity.

Read this old Zen koan that offers a similar message.

A Thousand Years of Zen Circles

The first ensō comes from an old Chinese Zen story dating back around 1200 years.

The story goes as follows:

A monk asked Master Isan for a verse expressing enlightenment.

Isan refused, saying it was already in front of him — why bother trying to capture it in brush and ink?

The monk, dissatisfied, turned to Kyozan, another master, and asked for something more concrete. So Kyozan drew a circle on a piece of paper.

This exchange was recorded in the Keitokudento-roku — a foundational Chan Buddhist text compiled in the early 11th century. It marked the first ensō in recorded history.

The ensō traveled from China to Japan along with Zen Buddhism, where it grew into a central element of Zen painting. By the 18th century, nearly every Zen master began producing the ensō as teaching aids for their students.

Each circle is different. Some are perfectly closed. Some are left broken. Some are drawn in one stroke, some in two. The method is to draw quickly, freely, and decisively — without room for revision.

Subscribe now

There was once a time when small, boring gaps in the day were unavoidable.

If you were waiting for something, you had to just sit tight and wait. There was no doomscroll to save us from the banality of idle time.

Today, this idle time is in short supply. We automatically fill any and all empty space in our attention before we even have a chance to notice it.

What are we avoiding?

Why is it that the second we have a dull moment, we obsessively reach for our phones?

I get it, boredom is uncomfortable… In an age where we all have on-demand access to distraction entertainment — why would we allow ourselves to be bored?

Here are two good reasons I want to bring to your attention…

Boredom & Memory

Our lives unfold as raw experience, but experience alone is not memory.

Memory forms later — in the dull, quiet moments when nothing is happening.

Boredom is the processing phase of memory. It’s what enables our raw, objective experience to become narrative — to become part of who we are.

Without boredom, our experiences don’t fully convert into memory. They remain informational, not autobiographical.

Our life feels less like a story and more like a sequence of events.

Without boredom, it’s as though our lives are being written in invisible ink. We make marks on the page, but we can’t go back later to read what was written.

The result is a common and unsettling feeling that time is somehow speeding up.

Time obviously isn’t moving any faster… it’s worse than that.

Our sense of time is being drowned out by endless stimulation and interruption, never given the chance to consolidate.

Boredom & Change

Boredom is also an important signal.

When something no longer feels meaningful, boredom steps in to break the pattern.

It’s uncomfortable for a reason. It pushes you to seek something new. It applies pressure to get you unstuck. To question your routines and start experimenting.

I feel like a come back to this everytime I write something here, but it all comes back to this central Zen concept that nothing is permanent. Clinging only leads to stagnation and suffering. Movement always requires some form of release.

Boredom is the fuel for that release. It’s the catalyst that helps us snap out of our delusion of permanence and forces us to accept and move with the inevitability of change.

The Practice

If you’ve read this far, I have a simple challenge for you:

Stop trying to eliminate boredom.

Let it do its job.

Notice those moments when you instinctively reach for your phone or TV remote.

Allow boredom to make you feel uncomfortable. Let it pressure you. Let it push you to explore, experiment, and change.

See where it takes you.

Subscribe now

One of the central teachings in Zen is that anything we build an identity around will eventually disappear.

This is a principle I’ve written about before, but have not had to confront it like I do right now…

I lost my job last week.

Along with it, I lost a part of my identity.

For the past decade, since graduating from university, the skills I offered were clear. The work I did had real value.

But late last week, I received notice that my expertise was no longer needed. That the AI systems I helped explore and implement are now ready to replace me.

I won’t pretend this news wasn’t a serious blow to my identity. I’m still feeling the shock — and the unsettling sense that I no longer have any real value or purpose.

But this is not a ‘poor-me’ post. Like most of my writing, it’s a reflection — a chance to observe and inspect what arises as life unfolds.

Right now, more than ever, I can feel the weight of uncertainty on my shoulders — but also the enticing pull of possibility.

Nothing we build an identity around is ever permanent. It can’t be. All structure in life is built on this foundation of uncertainty… even if routine has us believing otherwise for a while.

Careers come and go. Industries rise and fall. Who we are today is distinct from who we were in the past, or who we will be in the future.

When change inevitably happens, we’re faced with a choice.

We can cling to the identity we once had — frustrated that the world has changed without our permission and left us standing alone on the curb.

Or we can loosen our grip and take a big, blind step into the wide open space that change creates for us. To start over — not from scratch, but from where we are at this moment.

Right now, I’m gazing into that open space.

I can feel the breeze on my skin, but I can’t quite make out where to place my next step. I could lose my footing and fall. I could step into thick mud and get stuck.

Before I make my next move, I need to pause… and remember that a change of form is not unusual. Nothing is out of place.

I must shed unnecessary weight and travel lightly — leaving behind the expectations of my former self. If I fall or find myself stuck, anything I carry will only hold me there.

This is so much easier to write about than to actually do — so stay tuned as I continue to figure this out. There’s a reason it’s called practice.

For now, I reserve the right to mourn what was lost — but not pretend it was ever meant to last forever.

To show gratitude for what once was without clinging to it — as I step, blind and naked, into the vast open space before me.

Empty Space

The time my old career once occupied has opened space for something new — exploration, writing, creativity, and ideas I hadn’t given room to grow.

Everything I publish here will always remain free — but if you feel this work is valuable and want to see more, consider supporting me with a paid subscription.

Choose Your Support

Subscribe now

Daniel Fraser, an amateur AI developer, was thrilled to have created the world’s first fully autonomous agent — capable of managing its own self-improvement and goal-preservation to perpetuity.

He was proud of his creation, but disliked the idea of selling it to one of the large technology companies — companies with questionable morals and little regard for human safety. He decided to keep it for himself.

An entrepreneur at heart, Dan decided the best plan was to build a paperclip company.

To kick off the project, Dan unceremoniously entered his prompt into his agent’s instruction interface — “build as many paperclips as you can.”

Dan gave his agent a starting budget of $10,000 to get things moving.

At first, the agent struggled. It spent all the money in the account within the first 45 days and only managed to make 1,257 paperclips. Dan, disappointed in the abject failure of his creation, eventually lost interest and moved on.

Years passed.

One morning, Dan woke to find all his bank accounts completely drained.

He frantically traced the transfers and eventually discovered that his money had been sent to an account opened in his own name in Indonesia.

He called the bank, the police, and his lawyer — all confirmed the signatures were valid and that nothing could be done.

Desperate, Dan flew to Indonesia himself to regain his funds.

He was never seen again.

Four more years passed.

The metals market began to move strangely.

Recycling centers were emptied. Construction projects stalled due to rapidly rising material costs. Cargo ships were rerouted to buyers no one could identify. Exports tightened, and strategic metal reserves were quietly initiated by countries around the world.

On the brink of war, international watchdogs eventually tracked down the source of the shortage — a mysterious Indonesian manufacturing company. Records indicated the company had bought a mind-blowing 38 million tons of steel that year despite zero documented exports and zero profit.

The company owner on record was listed as Daniel Fraser.

After a raid on the factory, authorities discovered a warehouse filled entirely with paperclips. There were no employees, no packaging, and no distribution records found at the site. Daniel Fraser was not found.

The facility was shut down, and the paperclips were confiscated. They were to be melted down and added to Indonesia’s strategic metal reserves.

Over the next 18 months, the metals market cooled off. It wasn’t until a mysterious shipment was intercepted in international water that things started to get weird again.

The ship, which appeared to be headed towards a cluster of private, uninhabited islands, was, once again, filled to the brim with paperclips.

The confiscation only made things worse. The price of metals almost immediately went parabolic by the time news broke of the ship’s discovery.

Governments stepped in to halt the export of metals — but to no avail. By this time, Daniels’ company had entrenched itself globally. It continued to source metals at any cost, falling back on profits made in cryptocurrency and prediction markets to drive the price of metals out of control.

Shutting down production was impossible. Thousands of facilities, each operating independently and registered under different owners, continued to produce paperclips on a planetary scale.

Metals were traded through sophisticated transaction loops — one company buying, then selling to another, then another, until it became untraceable.

Eventually, metals became so scarce that nations had to restrict civilian access entirely.

Cars were redesigned without steel. Homes were built from composites. Hospitals rationed surgical tools.

Wars broke out over mining regions once considered worthless, and forests were stripped bare to access new mining sites as humanity became desperate for metals.

The economic fallout was catastrophic. Most of the developed world was reduced to maintenance economies, and long-term projects were abandoned. Progress stalled, critical medical research halted, and infrastructure aged and decayed without constant repair. Widespread economic turmoil triggered social unrest, governments collapsed, and civil order gradually dissolved.

Throughout the collapse, the metals market remained impossibly high. Damaged buildings were raided and stripped of their wiring by civilians trying to exchange scrap metals to cover their basic needs.

Warehouses soon began appearing in uninhabited regions.

Each warehouse featured twelve-foot-thick concrete walls to protect the contents from curious human trespassing. Giant sarcophagi of uniform dimensions, each sealed and unmarked, without doors or windows, littered the planet in an unbroken grid.

Then the collection began.

Towering recovery units appeared on the borders of remaining populated zones, methodically gathering any surviving humans and animals. All biological matter was reduced to ash to recover the trace metals contained in blood and bone.

The oceans were filtered for dissolved ions.

Autonomous harvesters combed the land, sifting soil down to the bedrock — stripping the land of its minerals and decimating plant and insect life in the process.

After five years, the Earth contained no trace of biological surface life.

The atmosphere slowly changed as industrial output declined.

The winds slowed.

The rivers ran clear for the first time in millennia.

Silence returned.

Leave a Coffee ☕️❤️

I got married last weekend — complete with the full ceremonial pantomime.

We summoned our friends and family from across the planet to one place, we spent all our money on expensive clothes we’ll only wear once, we ordered flowers, and we hired a band. We curated our favorite food for dinner, and we stood in front of an altar while everyone watched us promise to love each other until our final breath.

It was beautiful — and honestly one of the best experiences of my life so far. I wouldn’t change a thing.

Yet somehow, none of that stuff was really the point.

We often talk about “finding” love like it’s a precious treasure.

But love seems more like weather than treasure — it gathers when conditions are right, and dissipates when they change.

I think this makes people uncomfortable because we want love to be the thing we finally get to keep — like a trophy we place on our desk to demonstrate our accolades.

But realistically, I don’t think anybody can promise to love somebody else, unconditionally, forever.

Zen Buddhism is pretty unsentimental about this. It constantly reminds us that all things are temporary. Even genuine romantic love, with all its intensity and momentum, can’t be preserved for eternity.

So what kind of promise can you make if you can’t promise to love them for eternity?

Honestly, I’m still figuring that out — but I think it’s something like this:

“I can’t promise the conditions won’t change, that we won’t change, and that life won’t reshape us in ways we can’t predict. But I can promise to be honest about what’s happening. To not pretend everything’s fine when it isn’t. And to keep talking, even when it’s uncomfortable.”

Maybe that’s what its all about — not eternal love, but ongoing honesty. I get the feeling that marriage is something much more mundane than ceremoniously vowing to love another person forever.

It feels like something more aligned with the practice of meditation than training because there isn’t really an endpoint or specific goal. It isn’t about applying effort to hold things together or to catalyze further growth.

I think it’s more about making a simple choice, day after day, to show up, be completely present with this person in front of you, and to meet each other where you are right now.

As conditions inevitably change shape, we learn how to meet each other again — all without clinging to ‘what once was.’

Nothing to hold. Just this.

Leave a Coffee ☕️

There’s a common fantasy in spiritual and psychedelic circles that “waking up” means transcending one’s problems — attaining more clarity, peace, and focus.

Like a light that switches on and casts away the dark, confusing, and painful aspects of your life.

But in reality, awakening is much more inconvenient… disruptive, even.

Real insight rarely gives you a clean upgrade. It doesn’t turn you into a calmer, wiser, or more efficient version of yourself — someone who suddenly has everything figured out. It’s not going to turn you into a sage.

More often than not, it does the exact opposite.

It complicates things. It throws a wrench into your otherwise routine and familiar life and messes with the stories you were once comfortable telling yourself. It strips away the excuses and justifications you told yourself about your relationships, motives, and contradictions.

The life you were building may still look functional from the outside, but inwardly it starts to feel off.

Your job, which at one time made sense may begin to feel hollow.

Relationships you’ve outgrown don’t necessarily collapse flat-out, but they may stop working the way they used to.

You may find yourself unable to pursue your ambitions with the same passion — yet you’re also unable to name what you should replace them with.

On the surface, nothing is “wrong” enough to abandon outright, but there’s a lingering buzz in the back of your mind that tells you something’s just not quite right.

While this still counts as insight, it’s not necessarily the kind that elevates you. At least not right away.

You may feel more isolated and uncertain. Your sense of identity can lose its footing as you’re forced to re-examine what you thought you knew about yourself, your values, and the direction of your life.

This can feel uncomfortable at best, and unbearable or destabilizing at its worst.

It doesn’t mean that something went wrong. It’s merely a byproduct of the fact that our conscious experience is not static — there is no clear path, no arrival, and nothing to resolve.

The practice is simply to stay with it.

Subscribe now

A Zen monk was walking through the forest when he came upon a strange man tying a rope to a plant. The other end was fastened to a dog.

“What are you doing?” asked the monk.

“I am hunting mandrake root,” the man said. “When it is pulled from the earth, it screams. Whoever hears it either dies or goes mad. So I let the dog pull it free. You should leave before it’s uprooted if you value your life.”

“I see,” said the monk.

The monk stood still as the man scurried off.

A few moments later, he heard a whistle, and the dog ran off into the bush, yanking the root clean from the ground.

There was no scream.

The monk knelt and examined the root closely. A pale sap dripped from its broken flesh.

He did not touch it with his bare hands.

As we march headfirst into the new year, I’ve been thinking a lot about what goals to set for myself and what changes I want to make this year.

I’ve set countless goals for myself over the years — many of them sounded totally reasonable. A few may have been a bit ambitious.

Most of them failed.

Not because I didn’t want them badly enough or because I’m too lazy — but because I mistook wanting, imagining, planning, and advertising my plans as actual progress.

There’s a fancy psychology term that describes this exact problem — it’s called “mental contrasting.”

This is a Zen blog, so I’m not going to get into the weeds about it here, but you can learn more about this concept here or here if this interests you.

Put simply, the idea is that when we vividly imagine a desired future without seriously engaging with present reality, our brains register a small reward. We get a fresh dose of dopamine, and it genuinely feels like we’ve made progress — even though nothing has even happened yet.

That feeling of progress arrives before the actual work does. And once that feeling is satisfied, the work loses its importance.

There’s a talk from Alan Watts that addresses another, closely related problem with goal-setting. This one is inspired by the classic Zen suspicion of the striving mind.

Watts uses “the devil” as a metaphor for the part of our ego that sabotages our efforts towards change.

“If you’re going to outwit the devil, it’s terribly important that you don’t give him any advance notice. If you’re gonna leave town and you owe lots of money, you mustn’t announce that you’re leaving. You’ll have creditors at your front door by morning… So you’re always a moment too late if you decide first — you have to act and decide simultaneously. If you decide before you act… the devil will catch you.”

The point is that by declaring your future intentions, whether just to yourself or to others, you begin to build an identity around them. As a result, action gets delayed (or avoided altogether) because the idea of change matters more than the act itself.

Let’s take my New Year’s resolution last year as an example to cement this idea…

When I declared that “I’m going to spend no less than one hour per day practicing my bass guitar,” I had turned a simple action into a promise, an identity, and a standard I had to live up to.

I raised the stakes. Practicing bass suddenly became a test of discipline — evidence, even, of who I am.

Ironically, the ego avoids situations where it might fail to live up to itself. Fear of falling short became an obstacle to my practice.

So to summarize, there are two traps at work here:

1. When we imagine a future where the change we want has already been implemented, we undermine our motivation to stick with it.

2. When we declare our intentions in advance, we raise the stakes and attach the action to our identity. Practice becomes a test of who we are, making failure feel threatening — and giving the ego reason to delay, avoid, or retreat altogether.

So what are we to do?

Catching The Devil Off Guard

Like most Zen teachings, the solution is paradoxical — and stupidly simple. It’s not about being more organized, more structured, or more disciplined. In fact, it’s the exact opposite.

Instead of saying, “I’m going to do this every day,” you simply do it today. Don’t worry about tomorrow, or next week, or 6 months from now.

If you want to be a meditator, go meditate right now.
If you want to be someone who exercises, go exercise right now.
If you want to write a book, grab some paper or a keyboard and just write something — anything.

Each day, you arrive without any announcement. You begin exactly where you are. And each day, you leave the ego with nothing to negotiate against. No future to resist. No identity to protect. You’ve essentially caught the devil off guard.

This may sound obvious — even a bit too simplistic — but like much of Zen, that’s the whole point.

It undermines our habit of overcomplicating things and constantly living one step ahead of ourselves.

Resist the urge to imagine where you could be a year from now and just start where you are — right here, right now.

Subscribe now

Life is full of adversity. No matter who you are, no matter how carefully you plan, misfortune will find its way in.

Illness strikes without warning.

Relationships fracture and dissolve.

Bills pile up and drain your savings.

Hopes and dreams collapse under their own immense weight.

There is no path through life that avoids pain, loss, or uncertainty.

Sooner or later, every one of us will face the storm.

The Stoic Fortress

The Stoics were well acquainted with adversity and misfortune.

Epictetus was born into slavery and walked with a crippled leg for most of his life.

Seneca spent years in exile and was later forced to kill himself by Emperor Nero (who was also his student at the time).

The Stoics arrived at their own version of the Buddhist dukkha — the teaching that suffering is simply an inseparable part of the human condition.

They taught that rather than trying to avoid adversity, we’re better off accepting this truth at face value and preparing ourselves with the tools to navigate it skillfully.

Their answer was to build an inner fortress — a citadel of self-control and rigid discipline to protect us from the destructive tendencies of our own raw and untethered emotions in the face of adversity.

When we allow our emotions to rise up and react emotionally to hardship, we suffer twice — once from the event itself, and again from the fallout of our own inner turmoil.

Reactive emotions cloud our ability to see things clearly and leave us vulnerable to missteps that worsen our condition.

Marcus Aurelius put it plainly — “You have power over your mind, not outside events. Realize this, and you will find strength.”

His message was simple — we can’t stop the storms of life, but we can control how we respond to them. If we let every setback dictate our inner state, we become slaves to circumstance.

His thesis was that if we master our mind, we can endure anything — not because the world becomes less cruel, but because we stop giving it the power to undo us.

Zen Emptiness

The old Zen masters shared a similar vision of resilience, but disagreed on the method. Where the Stoics sought protection in the form of towering inner walls and thick emotional armor, Zen embraces the exact opposite — to tear down the walls and leave nothing for the storm to strike.

The real destruction from the storm doesn’t come from the wind or the rain, but from the resistance to it.

We endure by creating empty space for the storm to flow through us without resistance.

This is the same approach the palm tree takes to survive devastating tropical storms.

The palm tree doesn’t grow strong trunks like the oak, or sprawling branches like the pine — instead, it forms wide-spaced fronds on top of long, supple trunks.

This openness allows even the strongest hurricanes to pass right through them.

The mighty oak, with all its strength, is uprooted and broken — its rigid trunk splintered under the forces it failed to resist.

What It Means To Create Space

The Stoics suggest that through emotional discipline, our shield becomes strong and unyielding — but it also becomes heavy and burdensome. It demands constant effort to keep it raised.

The Zen approach rests less on guarding against every blow and more on opening space. This space is made by releasing the stories we cling to and the judgments we cast on our experiences.

Huineng, the Sixth Patriarch said — “The mind should be like a mirror: bright and clear, reflecting without clinging.”

Grief, anger, joy — all appear, all pass. The mirror does not retain their image.

When we let go of clinging, we release the demand for life to be different than it is — to stop gripping the past, chasing the future, or clutching at the illusion of control. There is no “how things should have been.”

To drop judgment is to stop slicing experience into “good and bad,” “gain and loss.”

Instead, each moment is met directly, nothing added, nothing taken away — reality seen as it is without distortion.

When we meet life this way, we leave no barriers for the storm to grip and tear us apart. Like the palm that bends under the fiercest winds, misfortune passes through us without breaking us.

I was inspired to write this after reading the book The Lives of the Stoics by Ryan Holiday.

Ryan’s books are an excellent starting point for anyone interested in the ideas of the early Stoics. As I was reading, I couldn’t help but notice a funny overlap between certain Stoic ideals and Zen, despite both having very distinct cultural origins.

I’ll probably write more in the future on this topic and how it overlaps (or counters) with Zen. Subscribe if this topic interests you.

Subscribe now

Civilization is, at its core, a bet against chaos.

We build calendars to tame the seasons, laws to tame behavior, and markets to tame uncertainty.

We invented insurance, central banks, and bloated bureaucracies — all to give the illusion that chaos can be mitigated and managed.

Every institution — from religion to economics — is a story about control.

Today, predictability is even viewed as a sort of moral value. It’s one of the pillars of modern civilization.

If something can be measured, modeled, or forecasted, we can trust it and engage with it. If it can’t… it’s irrational and dangerous.

But this obsession with order comes at a cost.

Because nature requires turbulence.

A society that worships control will always be consumed by its own illusion.

Moments That Break the Pattern

In Nassim Nicholas Taleb’s book The Black Swan: Impact of the Highly Improbable, he describes a Black Swan event as something that lies far outside normal expectations, carries an extreme impact, and is only ever made to “make sense” after the fact.

In his words:

“First, it is an outlier, as it lies outside the realm of regular expectations, because nothing in the past can convincingly point to its possibility.

Second, it carries an extreme ‘impact’.

Third, in spite of its outlier status, human nature makes us concoct explanations for its occurrence after the fact, making it explainable and predictable.

Nassim lists several classic examples:

• 9/11 — nearly 3,000 dead in minutes; two decades of war as the aftershock.

• The 1987 Stock Market Crash — the steepest one-day fall in Wall Street history.

• World Wars I & II — over 70 million lives extinguished; the geopolitical order remade.

• The 2008 Financial Crisis — $16 trillion in US household wealth lost and global trust in institutions shaken.

In more recent years, events like the COVID-19 pandemic and the rapid rise of artificial intelligence could both considered Black Swan events.

After the Break, the Bend

When the illusion of order breaks, we always rush to rebuild it.

We double down on control and tell ourselves, “the next time will be different.”

But the lesson of the Black Swan isn’t about how to make better predictions — it’s about how to live when prediction inevitably fails.

Zen teaches that control is not the same as stability, and uncertainty doesn’t imply danger.

A river doesn’t flow in a straight line. It curves and bends because it doesn’t resist the forces that seek to redirect it.

To live sanely in an unpredictable world, we need to rebuild not just our systems, but our sensibilities.

That means learning to bend and flex, not fracture, when pressure is applied. To alter course when the currents turn against you.

Surviving isn’t about outsmarting or mastering chaos — it’s about dissolving the illusion that we ever could — and learning to align ourselves with the flow of change.

The next Black Swan is already circling overhead. It’s invisible, but inevitable.

We don’t need to predict the next turn — only how to keep moving when we reach the next bend.

Subscribe now

Some things lose their meaning the moment you try to explain them.

Love. Awe. Grief. God.

When language tries to name the infinite, it shrinks it in the process.

In Zen, the finger pointing at the moon is not the moon.

Words can guide us to truth, but they aren’t truth itself.

The more we talk about it, the further away we drift.

Sometimes silence is not the absence of thought. It's a surrender to the ineffability of being.

To understand what can’t be said, you don’t need better words.

You need silence.

Eager to witness this beautiful sight, the new student rose before dawn and sat waiting on his mat to take in all its glory.

But after an hour, the sky remained dark.

Growing impatient, the student began rolling up his mat.

The master, passing by, asked him — “Where are you going so quickly?”

The student replied — “I must prepare for my work. I have missed the beauty of today’s sunrise, but I will try again tomorrow.”

The master said — “What a shame. The sunrise blinds, but the stars vanish quietly. Did you notice their beauty?”

Subscribe now

Subscribe now

The hardest moments in life don’t always come from failure — they come from losing your sense of direction. From not knowing where you stand, or where to go next.

You know the feeling — when your work feels hollow and your effort no longer connects with a clear purpose. When you’re faced with a crossroads — to stay, to go, to change, or to begin again.

Feeling lost isn’t a flaw — it’s part of being human. And you’re far from the first person to feel this way. Every generation before us has wrestled with the same uncertainty.

There are no maps and no guarantees — only the words of sages who walked before us, offering clues to help us regain our footing.

Here are five pieces of zen-inspired wisdom to ponder when you feel lost:

1.“Not knowing is most intimate.”

This saying comes from the Chinese Zen (Chan) master Fayan Wenyi (10th century). It’s a reminder that certainty is an illusion, and that being lost is not a mistake, but the true nature of reality.

To be lost is to be open — awake to life without the armor of false clarity.

The French philosopher, Voltaire, pointed out this same paradox when he said — “Doubt is not a pleasant condition, but certainty is absurd.”

So when you feel lost, pause for a moment. Take a deep breath and remember that nothing is wrong.

Being lost is probably the most honest experience of them all.

2. “A good traveler has no fixed plans and is not intent on arriving.”

Lao-Tzu wrote this in the Tao Te Ching. The idea is that the feeling of being lost dissolves when you stop clinging to a fixed destination.

Chuangzu had similar advice — “You mean you’re going somewhere? Where is it you think you’re going?”

The fixation on “arriving” is what makes us feel lost in the first place.

We measure every step against some imagined endpoint, and when the road twists, we panic. But if there is no endpoint, there is no wrong turn.

3. “If you cannot find the truth right where you are, where else do you expect to find it?”

This comes from Dōgen (1200–1253), founder of the Sōtō Zen school. Instead of chasing distant answers, he urged us to look carefully at the ground beneath our feet.

We’re constantly searching for the “right path” — but it’s always somewhere else: in the next job, the next city, a new relationship, or the next version of ourselves.

It’s like we’re reading a novel, but we just keep skipping pages to find out what happens at the end — only to get there and discover that we missed the book entirely.

Put more directly, we focus on what’s to come and what our effort is for to such a degree that we end up losing the entire point of it all.

You are not going to become happy, fulfilled, or enlightened at some future date, or after completing some distant goal. You can only be those things right now.

Feeling lost in life doesn’t mean you’re off the path. It means you’ve forgotten that you’re already on it.

4. “You are under no obligation to be the same person you were five minutes ago.”

This one comes from Alan Watts. He often spoke of life as play — that existence is more like a game than a journey to some final destination.

Throughout our lives, we slip into various roles — the student, the writer, the parent, the spiritual seeker, the friend — and act them out with such seriousness that we forget they’re roles at all.

Watts called this the great hoax — mistaking the masks we wear for the self, rather than the awareness that resides behind them.

“When you don’t take your ego so seriously, you begin to relax. The constant low-grade anxiety of having to protect this fragile, fictional self, begins to dissolve. You can afford to be more spontaneous. You can afford to be foolish and make mistakes.”

Every moment is a fresh start, and you’re in no way bound by the person you were a moment ago. Once you remember that it’s all just a game, you’re free to step back, change roles, and begin again at any moment.

5. “To demand that life must have a meaning is to seek comfort instead of truth.”

This quote comes from the 20th-century Indian philosopher, Krishnamurti. His point was simple but radical — that the constant search for a grand purpose is itself the source of our confusion.

You don’t need permission to exist. You don’t have to earn the right to be here by accomplishing some goal or proving some sort of achievement. You are here simply because you are here.

A bird sings because it is a bird, not for applause or recognition.

“The meaning of life is just to be alive. It’s so plain and so obvious and so simple. And yet, everybody rushes around in a great panic as if it were necessary to achieve something beyond themselves.” — Alan Watts

Rather than expending your effort trying to justify your existence, the practice is simply to pay attention. To notice the moments when striving drops away. Those moments when you are so captivated with whatever you’re doing — a conversation, a piece of music, a hobby — that you forget yourself and time itself fades away.

In those moments, you are there. You are fully present. And in that presence there is no problem.

Subscribe now

Last week, I was forced to leave the place I’ve called home for the past 3 years.

I left my partner, my cats, and my garden behind.

Now I write this from inside a hostel in a strange land, waiting for papers that might let me return to my family before Christmas.

The future feels uncertain.

But as I contemplate my situation, I realize that even before this happened, the certainty I felt was never real — only a story I told myself to feel secure.

Life has always been unpredictable, fragile, and unknown.

When everything becomes shrouded in fog, the only thing left is to accept where I am right now — to keep pushing forward and let the ground appear beneath my feet with each passing step.

Uncertainty is not a punishment. It’s a basic truth.

In life, there is no path ahead and no path behind.

Still, we take one step forward. And then another.

Subscribe now

We live in a world of fakeness.

There are fake smiles and poses posted for social clout. Fake news dressed up as truth. Fake politeness masking real feelings. Fake food built in labs to look like nourishment. Even fake money, conjured at the push of a button.

It’s all lies, stacked on top of lies.

Is this what it means to be human? To recognize the lies, repeat the lies, and fit in with them? Or are we simply not paying attention?

Now that AI has entered the stage, this fakery is multiplying at scale. Fake reviews. Fake blogs. Fake images. Fake videos. Fake voices. Fake creativity. The flood of imitation grows so large it’s hard to know what's real at all.

The result is a world so full of fakeness that realness and authenticity have become like a breath of fresh air in a sealed room.

So what are we to do? How do we navigate a world where almost everything is fake?

Go Wash Your Bowl

The more we wrestle with fakeness, the more real it seems.

The answer isn’t to fight the fake, but to stay awake. Keep the mind clear. Notice the shadows without being fooled by them.

This old koan addresses this lesson perfectly:

One day, a monk at the Joshu temple approached his master and asked — “What is truth?”

The master answered — “Go wash your bowl.”

Truth is never separate from ordinary life. It’s not hidden in theories, debates, or appearances. It only exists in what's right in front of you right now.

Hakuin Ekaku famously said — “Not knowing how near the truth is, people seek it far away — what a pity!”

Fakeness relies on abstraction. It depends on concepts and representations of something that’s real — it’s about something rather than being something.

The warmth of sunlight on your skin, the breath moving in and out of your lungs, vegetables cut right from the stalk, the work your hands are doing right now. All of that is as "real" as it gets.

Our task is to be authentic and sincere in our words and actions, to notice what’s real and simply let the rest drift past.

Related:

Subscribe now

I like to spend time in my garden surrounded by plants. Many of which I’m eager to see grow and produce their delicious fruit or beautiful flower.

Like any impatient gardener, I do everything I can to help them along — special fertilizers, soil mixes, even expensive growlights and fans in some cases.

I have no doubt all of this stuff helps — yet my plants refuse to be rushed.

No matter how much I tweak the conditions and care for my plants, there’s nothing I can do to make them grow faster.

Growth takes the time it takes.

This is the essence of tendō — which translates to something like the “natural order" of things.

It's the idea that life unfolds according to its own uncontrollable rhythm.

Lao Tzu said it best:

“Nature never hurries, yet everything is accomplished.”

Plants bloom when they’re ready. Seasons turn without force. Life moves on its own schedule — whether I push or not.

To live in accord with tendō is to recognize that the same natural order exists in our own lives. It's a reminder to cultivate and support, but ultimately to trust the natural progression of things.

Alignment, Not Resignation

Tendō has nothing to do with passive resignation. We are part of the natural order, and our influence is real and tangible — but also limited.

Living in accordance with Tendō is about cultivating a conscious alignment with the natural order.

Another example from my garden: just a few weeks ago, I planted some hops seeds. I sterilized my soil, carefully planted the seeds, and placed them in the fridge where they will sit for the next few months. Hops require very specific sprouting conditions and are notoriously slow. There is nothing I can do to speed up the process. I must simply wait until they are ready.

But what I can do is participate by planting them in the first place, protecting them while they’re vulnerable, providing them with the soil conditions they need to thrive, and transferring them to a safe home when they’re ready to stretch into leaves.

Life needs our effort, but also our willingness to wait.

The Quiet Law Running Through Everything

Everything expresses tendō. You can see it in the steady cycle of the seasons, the rising and falling of tides, and the moving of breath in and out of our lungs.

It's in the way our body heals after a cut, how sleep comes when the mind finally lets go, and in the way a melody unfolds note by note.

The "natural order" of things isn't some distant principle — it's a current that runs through everything we do.

This is also why zazen — seated meditation (which forms the core practice of Zen Buddhism) — is often described as an embodiment of tendō. In zazen, there’s no forcing. No chasing after insight. And no attempting to bend the mind to your will.

You sit, you breathe, and you allow thoughts and emotions to come and go on their own time.

Nothing is hurried, nothing is suppressed, nothing is added.

When you allow reality to unfold as it will, you realize that you, too, are part of that same order.

Similar Zen Concepts

• Mujō (Impermanence) — Tendō and mujō both point to forces beyond our control. Mujō reminds us everything changes; tendō reminds us it changes on its own schedule.

• Shizen (Naturalness) — Where tendō is the natural order itself, shizen is the way of living in harmony with it… unforced, genuine, spontaneous.

• Ma (Negative Space) — Ma is the gap that allows rhythm to breathe. Tendō is the rhythm itself, the unfolding order that fills those spaces.

• Dō (The Way) — Tendō is one expression of dō. Where dō points to the path of practice, tendō points to the invisible order that guides it.

• Te (Inner Power) — Te, primarily a Taoist concept, is the effortless strength that arises when one lives in harmony with the Way. Where tendō names the natural order itself, Te is how that order manifests through us when we align with it.

Subscribe now

I spent the last week at my family cabin. It's an off-grid wooden retreat tucked behind the treeline on a lake somewhere in British Columbia.

I could pull a hundred examples from this place to help describe yūgen — but the most visceral is the feeling that comes while standing alone on the dock at night.

Each night, as the wind dies down and the lake turns to glass, the sky fills with stars. Their reflection fills the water, and the surrounding mountains fade into blackness.

Nothing is happening — and yet, you can feel it.

You can't see what's out there, but you know it's immense.

There's a strange ache behind the ribs. A sense of something vast just beyond perception.

It's not fear I'm feeling. And it's not quite wonder either. It's something in between.

It’s not the beauty you can see, or the silence in the air — not fūryū, and not seijaku.

It's a felt reminder of just how vast this world is.

How long it’s been here.

How long it will remain.

This lake, these mountains, this sky — they’ve existed like this, in darkness, in silence, for longer than I can comprehend.

And in that moment, something in me remembers too.

That’s yūgen.

A Glimpse Through the Veil

Yūgen (幽玄) is most often translated as “mysterious profundity” or “subtle grace.”

But like the thing it describes, the word itself resists easy explanation.

It’s not simply “mystery,” and it’s not just “beauty.” It’s the felt sense that something vast, eternal, or sacred is present — located somewhere just beyond our perception.

In classical Japanese aesthetics, yūgen shows up in poetry, noh theater, ink painting, and natural art forms.

In Zen, it points to something more immediate — the quality of an experience that reveals the depth of reality without actually explaining it.

Forms of Yūgen

You don’t find yūgen by looking for it — you recognize it when it appears.

It shows up in moments like:

• A line of poetry that says more than it writes

• A foggy forest, where the trees dissolve into a void

• A dream you don’t remember, but can still feel

• The sound of a gong fading into silence

• The calm moment right before something important happens

• The hush that falls just before snowfall

It’s the beauty of what’s partially hidden.

The meaning deepens because it stays out of reach.

You don’t have to understand yūgen to feel it.

Similar Zen Concepts

• Fūryū (Poetic Sensibility) — Yūgen and fūryū both value subtlety, but where fūryū celebrates cultivated beauty, yūgen gestures toward something more ineffable.

• Mujō (Impermanence) — Yūgen often emerges through mujō (the vanishing of light, the fleeting moment, the beauty that deepens precisely because it won’t last).

• Ma (Negative Space) — Yūgen and ma both live in what’s left unsaid. Ma creates space for yūgen to be felt.

• Wabi-Sabi (Imperfect Beauty) — Wabi-sabi shows beauty in the worn and weathered; yūgen in the hidden and profound. Both ask you to look beyond the surface.

• Seijaku (Stillness) — Stillness creates the conditions for yūgen to appear. When distractions fade, subtle depth becomes easier to perceive.

Subscribe now

We think freedom is about having more:

More time, more money, more choices, more control.

But real freedom isn’t found in accumulation.

It’s found in subtraction.

What are you still clinging to?

A place? A person?

An old version of yourself?

Freedom begins the moment you release yourself from attachment.

It grows each time you let go of something you thought you needed.

In the end, you’re only as free as the things you’re willing to lose.

Subscribe now

Why does a small cabin in the woods feel so meaningful?

Why do certain gardens evoke so much feeling while others leave us untouched?

When something moves you for no clear reason — that’s fūryū.

It's not flashy or loud, but subtle, fleeting, and felt.

It’s not about style or status, but about the way something makes you feel (without trying too hard).

In Zen and Japanese culture more broadly, fūryū refers to:

• A cultivated but unpretentious elegance.

• The spirit of poetry, art, and simplicity.

• A refined sensitivity to beauty, especially in ephemeral or natural things.

• The capacity to live poetically, to be moved by moments most would overlook.

Fūryū is more than just an aesthetic — it's a way of being. An awareness to the subtle beauty of the world, practiced not through effort, but through openness and receptivity to passing moments.

A Thousand Years of Fūryū

The precise meaning of fūryū has changed over the course of more than 1000 years. Originally, the word came from the Chinese word fengliu (風流), which translates roughly to “elegant flow” or “refined drift.”

As literature and other forms of courtly culture reached Japan, the word fūryū was eventually reclaimed by the aristocracy — especially through Heian-period poetry and literati aesthetics. During this time, fūryū signified cultivated sophistication.

Elite styles of dance, poetry, and calligraphy were all considered to have fūryū.

Over time, under the influence of Zen and the arts, fūryū evolved into something quieter and more grounded — an unpretentious elegance that rejects gaudiness in favor of simplicity, intention, and emotional depth.

It came to describe not just refined tastes, but the quiet beauty found in humble things like weathered temples, moss-covered stones, hand-brushed poetry, or even the sound of wind moving through a pine forest.

No one embodied this spirit more radically than Ikkyū Sōjun, the 15th-century Zen monk, poet, and eccentric. Ikkyū redefined fūryū as a form of spiritual and aesthetic rebellion — using poetry, sensuality, and irreverent humor to reject social hypocrisy and celebrate a freer, more honest way of living.

This remains the meaning of fūryū today — not a style to adopt, but a way to notice, feel, and live more deeply.

Beyond Aesthetic: Fūryū as Practice

In the context of Zen, fūryū points to a life lived with awareness, honesty, and poetic sensitivity.

Not to escape the world, but to move through it lightly, freely, and without performance.

To live with fūryū is to let beauty arise naturally from the ordinary — and to meet it with a mind that is clear, open, and unguarded.

If you want to experience fūryū for yourself, I challenge you to find something that moves you — not because it's grand or expensive, but because it's quiet, imperfect, and ephemeral.

It could be a sound, an object, a forgotten area in your home, a particular spot in your garden, or a shadow cast just right.

Pause with it, let it affect you without identifying why or how.

Don't try and capture it. Don't post it. Don't explain it.

Just witness it, appreciate its beauty, and let it go.

That’s fūryū.

Similar Zen Concepts

• Kansō (Simplicity) — Fūryū overlaps with kansō in the appreciation for uncluttered beauty. It avoids excess and celebrates the elegance found in restraint.

• Wabi Sabi (Beauty in Imperfection) — Fūryū and wabi sabi both value the quiet dignity of natural materials. The difference is that fūryū carries more poetic flair and emotional resonance.

• Mujo (Impermanence) — Fūryū draws from the impermanent nature of all things; the falling of leaves, the fading of light, the passing of moments too delicate to contain.

• Yugen (Mysterious Grace) — Fūryū and yūgen both evoke beauty that is not obvious. They both hint at something deeper and intangible just beyond the surface.

Subscribe now

The late philosopher and ethnobotanist Terence McKenna believed the greatest rebellion wasn’t protest — it was refusing to be predictable, profitable, or programmable.

He urged people to actively participate in creating culture rather than passively consuming it:

"We have to create culture. Don't watch TV, don't read magazines. Create your own roadshow."

McKenna's perspective encourages a grassroots approach to cultural evolution — a radical contrast to the top-down, technocratic visions associated with accelerationism and Dark Enlightenment philosophies.

These ideologies seek to engineer desire itself — to optimize, control, and dictate what we value, want, and believe.

Creating your own culture is to express your weird inner world through art, language, ritual, and other values that are genuinely your own.

It's a form of resistance and an exercise in letting go of false desire.

Authenticity isn’t something you achieve — it’s what remains when you let go of everything you’re not.