I. Does It Make Sense To Write About Doubt?
If I still struggled as I have in the worst nights, I would never arrive at these sentences, nor will those truly doubting care to read them. Doubt garbs herself with midnight veils woven from her own hair beyond which our powers of certainty cannot peer. “Doubt this!” she cries to anyone who would understand her true nature. And yet, this is her downfall; her own garments eat at her. Doubt may always fairly be doubted. Therefore, let me write.

II. Doubt’s Superpower
Most of our demons melt in the light. Doubt eats the light for lunch.

III. How Doubt Reproduces Within Us, Eats Us From The Inside, And Leaves a Husk
I doubt my doubts are important.

IV. The Wonderful Phenomenon of Doubt in a Social Context
Small doubts are social creatures; doubt’s spawn flock to dorm rooms and coffee shops. Like moths, they are drawn to the light. Better: Like cannons, they are drawn to ships. The small vessels keeping us afloat on the inky depths of unknowing (and make no mistake, even the Hebrews needed dry land in order to walk and to breathe) are ruptured and sunk by the shot of other ships.

“There is no one to pray to,” they aim at your bow. “Your father doesn’t love you,” they snipe at your mast. You can try defending yourself with an argument, but the underlying message is, wouldn’t you prefer to be on a ship whose sky remains clear of iron? Shouldn’t you sail to a more defensible position?

The only response to this that ever works is to undercut their own certainty, to put a hole through their hull, to question their assumptions. You may sink them before they sink you. You may drown in the attempt.

Either way, it’s the sea that wins.

V. Can Philosophy Rescue Us From Our Doubt?
You can doubt that A=A, or that 1=1, or that Truth=Truth. You cannot, however, rationally doubt I=I, that you are yourself, for if you are not yourself, who is doubting? On the other hand, rationality is, itself, an A, not an I. Doubt everything.

VI. Why We Should Be Happy That Reason Is Powerless in the Face of Doubt
Doubt is abhorrent to nature. To frame the sun coming up tomorrow only as a probability is to ignore the sun’s nature and to reject reason, which exists to understand it. “Maybe the sun won’t rise” is technically true, and also calls into question whether there is a sun that has risen every morning for all of recorded history. If the sun’s nature is not responsible for this phenomenon, what is?

I, too, am like the sun. No matter how many times I’ve sinned, day in, day out, always the same, I might stop today. Inductive reason cannot tell me my nature; what I am (and thus, what I will do) is not determined by what I’ve done.

To repent is to doubt.

VII. Where does doubt come from?
The source of doubt is a Truth too great to be known.

VIII. Why We Should Be Sad That Reason Is Powerless in the Face of Doubt
Doubt does not feel like repentance when you have no sight of the G-dly revelation and your faith seems to have died and to believe you can rekindle something real in your creased and blackened heart is harder in your eyes than willing eleven billion dollars into your bank account in the next thirty seconds.

IX. On the Beliefs of Skeptics
“You can never be objective since you doubt only in the context of truths you’ve already assumed,” they say. They complain that doubt is only allowed, in certain schools of thought, in the context of faith. They never complain that their school of thought only accepts faith in the context of doubt. Sanitation workers should not be purists.

X. Since All Connection Depends on Faith
Doubt is to be alone.

XI. Is Doubt a Disease?
Doubt is both better and worse than an airborne virus.

It’s worse because the typical virus doesn’t demand your help to spread, doesn’t have you measuring your friends to determine who is ready for infection. It’s better because a good friend may not only remain a good friend despite infection, but their infection may be the cure for your own.

XII. Is It Rude to Ignore My Doubts?
Like the local branch of the KKK, there’s a big difference between having doubts around and entertaining them.

XIII. Doubt As a Tool
Doubt is a sharpening stone for the blade of faith. Perhaps the sword cannot cut through the stone. Hacking away at the rock will only blunt your faith. But the practiced warrior learns the art of attacking the stone with the right motion at the correct angle. The sword gets sharper.

Perhaps even sharp enough to cut stone.

XIV. Can Amalek Be Defeated?
The Rebbe teaches that Amalek grows with you. At the beginning of your journey, there is one kind of Amalek. Years later, when you have vanquished those doubts, their more refined children still rise against you. In a way, this is freeing, since you will not demand that any one answer vanquish Amalek forever.

Amalek’s ultimate downfall comes only with the answer of Moshiach, which is not really a single answer, but the totality of an unending motion of growth, the classroom of the unknowable Truth.

XV. Who Should Doubt?
“The best lack all conviction, while the worst/Are full of passionate intensity.” The first line is a problem, true, but can we really say, after the 20th century especially, that it’s worse than the second?

XVI. A Lie
“If He would just reveal Himself to me, I would no longer doubt.”

XVII. Faith Is A Match for Doubt
Just as Haman is special for knowing the truth and yet rebelling against it anyway, a Jew is special for doubting the truth and devoting themselves anyway.

XVIII. Trust
There is no human social system that can survive a pervasive breach of trust. Consider the Beit Din and its laws of testimony. If witnesses cannot be believed, nothing can be believed. Doubt’s last refuge is, therefore, paranoia. Even Haman didn’t try it.

This is why when the Tzemach Tzedek told the chassid, “Believe in G-d because you believe in me, and I’ve seen Him,” it is a good answer. The day it becomes a bad answer is a very bad day.

XIX. A Summary of Everything New We’ve Learned About Doubt the Past 500 Years
Proof is useless because the soul wants certainty, which proof cannot provide.

Certainty, like doubt, will meet you where you are.

XX. The Doubt of Purim
“There is no joy like in the world like the loosening of doubts.”

Purim was not an otherworldly miracle, lighting striking Haman on the point of his triangular hat. That would not remove doubt.

Purim was having no sign of G-d, living within His utter concealment, Haman ascendant, until the moment Haman was destroyed.

Apparently, doubt, too, is His domain…