First, as always, i trust everyone is safe. Second, i haven’t written a book review in quite some time, and for the second time, i finished “The Obstacle Is The Way” , by Ryan Holiday. Thus i was compelled by the reader gods to review said tome.
It is said that before entering the sea
a river trembles with fear.
She looks back at the path she has traveled,
from the peaks of the mountains,
the long winding road crossing forests and villages.
And in front of her,
she sees an ocean so vast,
that to enter
there seems nothing more than to disappear forever.
But there is no other way.
The river can not go back.
Nobody can go back.
To go back is impossible in existence.
The river needs to take the risk
of entering the ocean
because only then will fear disappear,
because that’s where the river will know
it’s not about disappearing into the ocean,
but of becoming the ocean.
~ The River Cannot Go Back by Kahil Gibran
So, Dear Reader, you have before you this insurmountable situation, this issue, this frustration, or perhaps the looming public-speaking engagement that has already occupied far more psychological space than the event itself deserves. What if, buried somewhere inside any of the aforementioned, there is actually something beneficial for you not because every hardship arrives carrying a neatly wrapped lesson, but because almost anything can become useful once you stop allowing it to dictate the story?
i decided to re-read “The Obstacle Is The Way” by Ryan Holiday. For those who have read my blogs or actually know me, I am pro-reading a book three times. This comes from the book “How To Read A Book.’
Holiday’s central idea hit me like a wave against a sheer cliff: “What stands in the way becomes the way,” a line he pulls directly from Marcus Aurelius’ Meditations, which i had just happened to reread for the third time, this time more for comparison than consolation.
He is talking about Stoicism, of course, though not the dusty, marble-bust version taught as an elective and promptly forgotten. This is Stoicism adapted for the modern grind and organized around three disciplines: perception, action, and will. Perception is the ability to separate the event from the elaborate tragedy your ego has constructed around it; action is the deliberate movement that follows; and will is the internal architecture that remains when circumstances have removed nearly every other form of agency.
Holiday begins the discipline of perception on page 11, but the idea becomes useful around page 19 in “Recognize Your Power,” where the distinction emerges between what has happened and what we choose to make it mean. The obstacle is real; the helplessness surrounding it is often manufactured.
This becomes sharper in “Alter Your Perspective” on page 36. Perspective is not positive thinking, nor is it pretending that something objectively awful is secretly wonderful. It is the ability to change the frame without changing the facts to step far enough outside the situation that you can see its actual dimensions rather than merely experience its emotional gravity. i have started to deeply use this saying in difficult situations: “Perspective vs Perception”.
Perception and perspective are often treated as interchangeable, but they operate at different layers of the mind. Perception is the immediate interpretation of the emotional and cognitive machinery deciding what the obstacle means the moment it appears, while perspective is the distance we create afterward, the ability to step outside ourselves and see the same event within a larger system, timeline, or set of possibilities. Perception says, “This is happening to me”; perspective asks, “What is actually happening here?” One governs the first reaction, the other determines whether that reaction becomes a prison.
That is considerably more difficult than it sounds. It requires self-reflection and awareness of self.
Besides death, all failure is psychological.
—Jocko Willink
One nit for me is that the book occasionally leans too heavily into motivational-poster territory, where every failure becomes an opportunity, every rejection a redirection, and every collapsing building apparently an invitation to admire the architecture on the way down.
Not every obstacle is a conveniently positioned stepping stone. Some are institutional, irrational, or manufactured by mediocre people who protect comfortable systems; some consume years, damage confidence, and yield very little beyond the knowledge that you should never repeat the experience. Critics who dismiss the book as “airport Stoicism” are therefore not entirely wrong, because its formula can feel shallow when the problem is more serious than a missed deadline or an uncomfortable meeting.
Yet perhaps that criticism also misses the utility of the thing. A survival manual does not need to explain the complete nature of suffering; sometimes it merely needs to help you survive the night.
Rejection becomes evidence that we are unworthy. Being ignored becomes proof that we are irrelevant. An organization’s inability to use us becomes a verdict on whether we had anything useful to offer in the first place.
Rarely is any of that true. It is our ego that is talking to us, and by us, i mean the various forms of YOU.
Take, for example, ice skating. Sometimes the rink is simply too small not in its dimensions, but in what it permits you to become. Sometimes the coaches, judges, or skaters around you lack the imagination, patience, or courage to understand a different line, a different rhythm, or a program that does not fit neatly inside the expected form. Sometimes the system is built to reward repetition, protect hierarchy, and favor the technically familiar over the artistically dangerous. And sometimes you step onto the ice believing you were invited to skate your own program, only to discover that everyone else expects you to trace the same circles, hit the approved marks, and never venture too far from the boards.
Personally i prefer artistically dangerous.
Holiday’s “Live in the Present Moment,” beginning on page 45, is useful here because the mind loves to convert one obstacle into an entire imaginary future. A stalled initiative becomes a ruined career; a difficult conversation becomes permanent exclusion; one emphatic NO becomes evidence that every door ahead is already locked.
The present is usually less catastrophic than the mythology we build around it.
Years ago, in “FLAW: Not Thinking Big Enough or What Is Success?”, i wrote that we almost never think big enough in our endeavors, and when we finally believe we are approaching something audacious, grandiose, or stupendous enough, the word NO begins arriving from every direction.
No, you cannot do that.
No, it has never been done.
No, the organization does not work that way.
No, the market is not ready.
No, you are not the one.
The point was not to celebrate rejection for its own sake, or to pretend that every person saying NO is secretly frightened by your brilliance. Sometimes NO is valuable information; sometimes the idea is wrong, the timing is terrible, or your execution is deficient. The discipline is learning the difference between a warning and the gravitational pull of people who have mistaken familiarity for truth.
Every NO becomes another artifact from the boundary between what already exists and what someone is attempting to create. As I wrote then: for every NO you collect, you are one step closer to your success, not because success is cosmically guaranteed, but because anything genuinely new must first survive contact with those who cannot yet see it.
However, most often you are correct in your endeavor, just making it even more audacious. When the vision remains intact after honest inspection, collect the NO. Keep moving EverForward!
Interesting note here: i used Google’s NGRAM viewer to look up the usage of the word NO. It appears to have heightened in the mid-1940s and 1980s and has declined since then. Does that mean everything is OK? Note to self, i need to research why that happened.
That is where Holiday’s “Finding the Opportunity,” on page 53, becomes more sophisticated than the usual command to remain positive. The opportunity is not always hidden inside the obstacle like a prize in a cereal box. Sometimes the opportunity is information: the NO reveals who has imagination, where the system is brittle, which assumptions are protected, what must be rebuilt, or whether the work belongs somewhere else entirely.
Both resistance and acceptance produce a signal. Knowing which to parse is the perspective.
The Stoic response is therefore not to pretend the rejection does not hurt, nor is it to remain perfectly still while someone repeatedly strikes you with a hammer. Acceptance is not resignation. Resignation says there is nothing to be done; acceptance says this is the terrain, these are the constraints, these are the NOs I have collected, and now I must decide where to place my feet.
You may not control whether someone recognizes your value, but you control whether you continue creating it. You may not control whether an organization changes, but you control whether its inertia changes you. You may not control the politics, personalities, budgets, titles, markets, or invisible forces rearranging the board while everyone insists the game is fair, but you still control the quality and direction of your next move.
God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.
~ Niebuhr – edited newer version
Which brings us to page 60: “Prepare to Act.”
Perception without action is simply a more sophisticated form of paralysis. You can understand every incentive, diagnose every dysfunction, identify every character flaw, and map the entire system down to the last trembling bureaucrat, yet none of that matters unless the understanding changes what you do next.
Perhaps the obstacle forces you to sharpen the argument, exposes a weakness that confidence had concealed, or teaches you that title and authority are not remotely the same thing. Perhaps it reveals that the mountain you have spent years climbing is leaning against the wrong wall.
Or perhaps it simply teaches you when to leave.
The obstacle becomes the way because it forces a decision that comfort would have permitted you to postpone. Friction produces information; resistance creates a signal; and failure, humiliation, stalled initiative, public stumble, an executive who underestimated you, or the latest addition to your collection of NOs all contain data, assuming you can extract it without letting the noise consume you.
An event is not an identity. A mistake is not a destiny. An obstacle is not a verdict. It is the terrain.
These words, passed down from the ancients, will carry me through every adversity and maintain my life in balance. These four words are: This too shall pass.
I will laugh at the world.
~OG Mandino
The Obstacle Is the Way is not a deep philosophical treatment of Stoicism; it is closer to a survival guide for the modern grind, a neon sign flickering in the darkness and reminding you to keep moving not blindly, not cheerfully, and not while pretending pain is somehow beautiful, but deliberately.
The obstacle may not have appeared for your benefit; life is not always that poetic. Once it is there, however, what you make from it belongs to you.
The insult can become clarity. The rejection can become direction. The frustration can become fuel. The public-speaking engagement can reveal a voice you did not know you possessed. The institution that refuses to change can teach you never again to confuse position with power, activity with progress, or inclusion with influence.
And the roadblock may finally force the question you should have asked long ago:
Why am I trying so hard to travel in this direction?
Perhaps the obstacle is not testing your commitment to the path.
Perhaps it is telling you to choose a better one, or even a harder one, which, Oh Dear Reader, is the best way as far as i am concerned. Always choose the hardest path. The untravelled path yields what i call “firsts”. It also has the best memories and stories later on in your life.
Do The Thing and get the courage later.
~ Joseph Campell
So, Dear Reader, when you find yourself standing before the impossible thing, resist the instinct to ask why this is happening to you. Ask what it is showing you. Separate the event from the story, study the terrain, collect the NO, and take the next deliberate action while preserving enough fire within yourself to recognize the next opportunity that will manifest itself in the #EverFoward!
Until Then,
#iwishyouwater <- Humans getting the real memo. Go Live. April 2026 Massive South Swell Zicatela Beach, Mexico.
Ted ℂ. Tanner Jr. (@tctjr) / X
Muzak To Blog By: Sugar Candy Mountain, 666, groovy 1960s throwback psychedelica.
