CHAPTER FIVE
"I'll Start When I'm Ready"
The readiness that never arrives
"There is nothing in the world I would not dare to confront, now that I have girded on this sword."— Miguel de Cervantes, Don Quixote
I know a woman who has been preparing to write a novel for eleven years.
She has notebooks filled with character sketches. She has software for plotting and outlining. She has attended workshops, read books on craft, joined writing groups. She has purchased special pens, designated writing spaces, subscribed to literary magazines.
She has not written the novel.
Not a single chapter. Not a completed first draft. Not even a sustained attempt that failed. Eleven years of preparation for a journey that has never begun.
When I ask her about it, she says the same thing every time: "I'm not ready yet."
She means it sincerely. She believes that somewhere ahead is a state of readiness—a moment when she'll have enough knowledge, enough skill, enough confidence, enough something to finally begin. She's waiting for that moment.
It will never come.
THE READINESS MYTH
"I'll start when I'm ready" is the second great lie of deferral.
Where "there's always tomorrow" steals time by assuming infinite supply, "I'm not ready" steals it by assuming a threshold that must be crossed before action becomes possible. Both lies serve the same master: the part of us that is terrified to begin.
The readiness myth works like this: we imagine a future version of ourselves who is capable, confident, prepared. That future self has read enough books, practiced enough skills, resolved enough doubts. That future self can handle the challenges we currently fear.
And so we wait for that future self to arrive. We prepare. We gather resources. We consume information. We build elaborate launchpads while the rocket rusts.
"We suffer more in imagination than in reality."— Seneca, Letters from a Stoic, Ch. 13 →
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Seneca knew: the suffering we imagine—the failures, the rejections, the humiliations we fear—is almost always worse than reality. The monster under the bed is more terrifying before you look than after. But looking requires beginning. And beginning requires abandoning the myth that you need to be ready first.
Here's the truth no one tells you: readiness is not a prerequisite for action. Readiness is a consequence of action.
You don't get ready and then start. You start and thereby become ready.
THE KNIGHT WHO WASN'T READY
Don Quixote was not ready to be a knight.
He was an aging Spanish gentleman whose brain had been addled by too many chivalric romances. His armor was rusted and outdated. His horse, Rocinante, was a worn-out nag. His "lady" Dulcinea was a peasant girl who didn't know he existed. His squire Sancho Panza was a simple farmer who signed on for the promise of an island to govern.
By any reasonable measure, he was the least ready knight in the history of knight-errantry.
He rode out anyway.
"When life itself seems lunatic, who knows where madness lies? Perhaps to be too practical is madness. To surrender dreams—this may be madness... Too much sanity may be madness—and maddest of all: to see life as it is, and not as it should be!"— Miguel de Cervantes, Don Quixote →
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The "reasonable" people in Don Quixote's village stayed home. They waited until conditions were right. They prepared for adventures they would never take. They watched the lunatic ride off toward windmills—and they did nothing.
Cervantes isn't simply mocking Quixote. He's asking: who is really mad? The man who begins before he's ready, or the people who spend their whole lives getting ready and never begin?
The villages of the world are full of people who are "almost ready." They've been almost ready for years. They will be almost ready when they die.
Meanwhile, the unready knight rides into legend.
PREPARATION AS PROCRASTINATION
Let me be clear: preparation isn't bad. Learning is valuable. Practice matters.
The problem is when preparation becomes a hiding place. When "getting ready" is actually "avoiding starting." When the research, the planning, the gathering of tools serves not to prepare for action but to postpone it indefinitely.
You know the difference in your body. Genuine preparation feels like building toward something—energy accumulating, momentum growing, the launch approaching. False preparation feels like treading water—busy but static, always circling back to the same starting point.
The woman preparing to write her novel? She's not preparing. She's hiding. Every workshop attended is another year of not facing the blank page. Every craft book read is another chapter of the novel not written.
"Putting things off is the biggest waste of life: it snatches away each day as it comes, and denies us the present by promising the future."— Seneca, On the Shortness of Life →
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"Promising the future" is exactly what the readiness myth does. It promises a future state where beginning will be easy, where the fear will have dissolved, where you'll finally feel capable. And in promising that future, it steals the present—the only place where beginning is actually possible.
THE FROZEN PRINCE
Shakespeare gave us the ultimate portrait of paralysis by preparation.
Hamlet knows what he must do. The ghost of his father has revealed the truth: Claudius murdered the king and took his throne. Justice demands action. Duty demands action. Everything Hamlet believes demands action.
And yet he doesn't act. For scene after scene, he delays. He doubts. He tests the ghost's claims. He stages plays. He philosophizes. He delivers soliloquies about whether to be or not to be.
He's not ready.
"Thus conscience does make cowards of us all; And thus the native hue of resolution Is sicklied o'er with the pale cast of thought, And enterprises of great pitch and moment With this regard their currents turn awry, And lose the name of action."— William Shakespeare, Hamlet →
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"The pale cast of thought"—the sickness of overthinking. Resolution becomes cowardice. Great enterprises lose their momentum. Action dissolves into endless deliberation.
Hamlet is the patron saint of those who are getting ready. He thinks himself into paralysis. He knows so much about what he should do that he cannot do it. His readiness recedes the more he pursues it.
When he finally acts, it's too late. Everyone dies. The readiness he waited for never came—and the delay cost everything.
THE TRUTH ABOUT STARTING
Here's what the beginners know that the preparers don't:
The fear doesn't go away before you start. It goes away after you start.
You cannot think your way out of fear. You cannot prepare your way past it. You cannot read enough books or attend enough workshops or gather enough tools to make the fear of beginning disappear.
The only thing that dissolves the fear of beginning is beginning. The act itself is the antidote. Five minutes into the thing you've been dreading for months, the dread evaporates. What remains is just... the work. And the work is almost never as terrifying as the anticipation of the work.
"Do not wait to strike till the iron is hot; but make it hot by striking."
— William Butler Yeats
The iron is never hot when you're waiting for it to heat. The conditions are never right. The moment never arrives when everything aligns and beginning becomes easy.
You make it hot by striking. You create the readiness by acting. The confidence you're waiting to feel is on the other side of the beginning you're avoiding.
BEGINNING BEFORE READY
How do you begin before you're ready?
Accept that you will be bad at first. This is not failure—this is the necessary first stage of anything. No one writes a good first draft. No one runs a good first mile. No one gives a good first speech. Badness is the price of beginning, and it's a price worth paying.
Shrink the beginning. You're not writing a novel—you're writing one sentence. You're not changing your life—you're changing this afternoon. The smaller the beginning, the less resistance it meets. Make the first step so small that "not ready" becomes absurd.
Set a timer. Ten minutes. Just ten. You can endure anything for ten minutes. When the timer ends, you can stop—or you can continue, now that the spell of not-starting has been broken. The hardest part is always the first minute.
Remember the dying. The people on their deathbeds, the ones we'll meet in later chapters—they don't regret the things they tried and failed. They regret the things they never tried. They regret the readiness they waited for while life slipped away.
"Waste no more time arguing about what a good man should be. Be one."— Marcus Aurelius, Meditations, Ch. 10 →
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Stop arguing. Stop preparing. Stop debating what a ready person looks like.
Be. Do. Start.
The readiness will come—but only after you've already begun.
Key Insight
Readiness is not a state you achieve before beginning—it's a state you achieve through beginning. The confidence, the skill, the clarity you're waiting for exist only on the other side of starting. You cannot prepare your way to them. You can only begin your way to them.
The Discernment
Ask yourself: How long have I been "getting ready" for this? If the answer is more than a few weeks, the preparation has become procrastination. True preparation has an endpoint—a date when you will begin regardless of whether you feel ready. Set that date. Make it soon. Watch how the preparation suddenly accelerates when it has a deadline.
The woman with the eleven-year novel preparation? She's not unusual. She's most of us, in different domains. The business we're going to start. The relationship we're going to repair. The life we're going to live—someday, when we're ready.
Someday is a thief. Readiness is its accomplice. Together, they steal the years while promising that real life is just around the corner.
But there's another lie, perhaps even more insidious. It concerns the words we leave unspoken, the love we assume is understood, the conversations we'll have "when the time is right."
That's next. And it's urgent—because the time may never be right, and the words may never be said.
Unless you say them now.