On the weight of unpreparedness
Crossing the Rubicon.
If you look closely, squint a little, tilt your head just right, you’ll notice that you are, in fact, a subscriber. A willing participant, though when exactly you signed the dotted line remains a mystery even to you.
"Why am I here?" you ask, with the dazed bewilderment of a he/she/they waking up on a Freaky Friday. "Who is this unseen hand that dares summon me?"
Well, old sport, I won’t be answering any of that.
But I will say this: your free will is a charming illusion, no more real than the last sip of a drink you swore you hadn’t finished. You are here because you are here, as inevitable as the end of a tunnel, as inexplicable as the choices that brought you to this very moment. Fate? Coincidence? Some divine joke? Who’s to say? But let’s not pretend you ever really had a choice.
You may beat on, boat against the current, you will still be borne back ceaselessly into the algorithm, unless, of course, you share this post. Because if you don’t, my friend, I fear the choice was never yours to begin with. Take the wheel. Steer the course. Defy the system before it writes your ending for you.
I hope you have been well, dear reader?
As some of you may already know, I am more often than not, chronically online. Yes, I saw your text. Yes, shade seen. I will still post on my story.
On Twitter—formerly X (because when has “X” ever been anything but former?)—I stumbled upon a tweet by Red Jewel. A truly profound one. It reached through the static of my comfortable distractions, shook me by the collar, and in that moment, I knew: this was not a tweet to scroll past. This was a whisper from the universe, a nudge toward something worth creating. Thank you, Tee.
There is a peculiarity in human nature that is often overlooked, not because it is subtle, no. But because it is so enormous that it takes up the whole sky. It is the same thing that causes men to pray for rain and yet bring out their smallest cup to catch it. This is not the foolishness of ordinary men, who merely misunderstand their own limits. No, this is the grander wittiness of those who claim to understand the laws of the universe and yet behave as though the heavens will shrink themselves to fit their tininess.
The world is not kind to those who wait with small cups. I have seen them, perched on the street corners of destiny, their hands outstretched, while they wait for some celestial drizzle to fill their modest vessels. Again, the world is not kind to those who shrink themselves. It is not.
I pen this for my sake, for your sake, that you and I will not be unprepared. I do not want to speak of preparation, yet build no barns, waxing lyrical about greatness, yet carry a beggar’s purse. I do not want to ask for rain and cower beneath their awnings when the clouds break.
This is not the way of those who make history. The ones who shape their fate do not ask for rain and wait with a cup. They stand in the field with barrels and basins, ready to catch the downpour when it comes.
You see, It is a quite a simple principle, but the lots of us today are consumed with hesitation, the one that makes an art of expecting everything while preparing for nothing. We are a race of people who sit beneath the heavy clouds and murmur that we hope they will break, yet tremble when they do, then scurry for cover rather than raising our hands in triumph.
The problem is not merely that we lack the foresight to prepare; it is that we have mistaken smallness for humility, and largeness for arrogance. We have assumed that to carry a bucket where others carry a cup is to be presumptuous, when in truth, it is the only rational way to live. A man may err by preparing too much, but his greater error is to prepare too little.
And thus, I lead you to the curious case of the man who did prepare. The man who built his house, stacked his fortunes, and reached toward the stars, and yet, in the final stroke, failed not for lack of effort but for an excess of nostalgia. The man who stood at the shore and begged the sea to return to him—Jay Gatsby.
The Great Gatsby is one of my favourite books on the planet. A novel of preparation, but also of misplaced expectation. It is the study of a man who, by all accounts, did everything right and yet failed catastrophically. It is tempting to say that Gatsby’s ruin came from ambition, but that is a popular misreading, born from the current fashion of eating the rich. His ruin came not from ambition, but from an ambition that was fixed upon the past.
And here, in this seemingly personal tale of longing, we see a universal truth. We do not fail because we dare too much, but sometimes because we dare in the wrong direction. The miser who stores up treasure in a cave only to be buried with it is no less ambitious than the king who builds a kingdom, yet the latter thrives while the former perishes. Gatsby was prepared for rain, yes—but he was prepared for a rain that had already fallen, for a moment that had already slipped through his fingers. He built a monument to yesterday, when all monuments should be built to tomorrow.
If your bucket is out for the rain, ensure it is not turned upside down. Ensure it faces the sky.
But—and here is the real lesson—Gatsby was, at the very least, prepared. He built. He stretched himself toward the infinite. He was guilty of folly, yes, but it was the grand, romantic folly of a man who believed too much in possibility rather than too little. If Gatsby is to be criticized, it must be in comparison to those men who neither dream nor build, but merely stand still, cup in hand, waiting for something to happen.
There was once a time when men were criticized for trying to reach too high, for attempting to pluck the forbidden fruit from the heavens. The Greeks told stories of Icarus; the Bible warned of the Tower of Babel. But in those days, at least, failure came from audacity. Now, failure comes from something far worse from an age that does not even dare to reach.
We are told from birth that prudence is wisdom, that waiting is virtue, that to build great things is to invite disaster. We will learn that to dream too vividly is to be mocked, that to strive too fiercely is to be feared. That to be brave is to be cringe. That to act is to be performative.
We are trained, not for action, but for caution—a caution that does not protect us, but simply ensures that when the moment arrives, we will be unready.
History is filled with men and women who waited for a sign. They saw omens, they watched the stars, they waited for "the right time." And then, there are those who, like Caesar crossing the Rubicon, like Napoleon marching through the Alps, like Da Vinci sketching flying machines centuries before flight was possible knew that waiting is often a polite word for wasting.
Opportunity, that elusive specter, does not arrive with the grace of a well-mannered caller. It does not tap gently at the door while the world composes itself for the occasion. No, it bursts in like a gust off Long Island Sound. It rattles the asbestos and sends the careless scrambling for their footing. It appears in the languid hours of a summer’s night or in the midst of a tempest when the prudent have long since shuttered their windows. And those who grasp it, those rare, glittering figures are not the ones fumbling for their cufflinks, but the ones who, long before the knock came, had already set the wine to chill.
The universe rewards those who act as if the universe is on their side. That is to say, men who prepare for fortune, more often than not, find it—if only because they have become the sort of men who know what to do when it arrives.
The man who scatters his seeds upon the desert sands is indeed foolish, yes—but the one who clutches his seeds in trembling fists, while he whispers curses at the sky, is the greater. And yet, this is the quiet tragedy of our world today: we shrink from building for fear of ruin, we smother our dreams lest they crumble in the morning light. And so we stand in fields long abandoned, we speak of droughts and misfortune and never daring to look down at our own unturned soil, never admitting that it was our own hands that left the earth barren.
The universe, in all its baffling and brilliant comedy, is an absurdly generous host. But it only gives to those who behave as if they expect to receive. It is an old secret, known to gamblers and mystics alike, that luck follows those who prepare for it. The man who believes in fortune, who stacks his house with abundance, who stands ready with barrels instead of cups—he is, by the strange physics of existence, far more likely to find himself in the path of abundance.
The man who prepares increases his luck surface area.
I have asked for rain, I will not wait with a cup. Opportunity will not meet me unprepared.
There are those who drift upon the tides of destiny, believing it to be some great, indifferent current that carries them where it will. I have never been one for drifting. Destiny, to me, is not the hand that deals the cards but the force that dares to play them. If the doors of fortune are barred, I will not wait for a knock, I will carve my name upon the wood. If the roads are swallowed by dust and time, I will press forward still. I shall lay the stones with my own two hands. I do not ask the world for softness, nor do I expect its mercy. I ask only this: that when the hour strikes, I will rise to meet it, unshaken, unafraid, and utterly prepared. I hope you will too.
I have seen too many small cups. I have seen too many men and women waiting for fortune to fall into their laps. I have seen too much hesitation, too much caution. But caution is not wisdom. Fear is not prudence.
The man of faith who brings out his cup during the rain assumes that the universe, been so vast and so infinite, will politely confine itself to his narrow expectations. He assumes that his God, having created storms and rivers, will shrink Himself to fit the timid dimensions of his fear.
But God, if He is anything, is not small. He is lavish. He is excessive. He pours wine until it overflows. He rains manna until it covers the ground. And the universe, whether by accident or by design, behaves the same way. It does not trickle. It pours.
Let us not be found waiting with cups. Let us be the ones who, when the rain comes, are ready to catch an ocean.
For the fault is not in our stars.
And the die is not merely cast.
It is thrown by the hands that dared to grasp it.
May the winds carry you onward.
If substack had the highlight feature, I would have riddled this post with them. Each paragraph carried the pleasant weight of distilled wisdom.
This is extraordinary 👌