Don’t Ask the Calculator the Wrong Question

On math, money, and life in the middle

My mom is turning 80. She’s learning magic.

Card tricks. Sleight of hand. The kind where something impossible happens right in front of you and you feel that little jolt—wait… what?

She even hired a private tutor. Some guy in San Francisco. I picture him in a black cape in a dark, candle-lit basement somewhere in the Mission.

She spent years as a math therapist, helping high school students work through their fear of numbers. And it worked.

And now she’s paying to learn how to create that same feeling on purpose.

She even has a name: The Great Wendini.

It makes me think about the relationship between good magic and bad math.

I remember teaching algebra in summer school. I was looking away but asked a student, “What’s the square root of 25?”

She said, “4.89.”

I almost choked on my drink laughing.

“How on earth did you get that?” I asked.

“It’s what the calculator told me,” she said.

That’s the moment. Not a math mistake—a trust mistake.

She didn’t trust herself to try—she checked what the machine said.

Math is logical. Structured. Deterministic.

At least in theory. If you follow the steps, you get the answer. And yet, for a lot of people, it feels like magic. Because for whatever reason—fear, boredom, impatience—they don’t engage with the steps. Only the result.

Annie Duke calls this “resulting”—judging decisions by outcomes instead of process.

Sound like life?

Calculators, spreadsheets, markets, AI—they all compress the process.

They turn understanding into answer. Allen Iverson was “The Answer”—but what’s the question?

They turn input into output.

Clean. Fast. Efficient.

And completely opaque if you don’t know what’s happening in between.

That “in between” is where meaning lives.

But it’s also where things get uncomfortable.

Remember the annoying math teacher who made you write out every step?

There was a reason for that.

Real systems don’t just change one variable. They change many at once.

A matrix, if you want to call it that. Something that mixes inputs, weights them, transforms them.

So the output can feel surprising. Or wrong. Or magical.

Not because it is—but because you don’t see how it got there.

The same way it takes 11 years to become an overnight success.

I see people do this with investing.

We hear, “The market returns 10%,” and think: put money in, get more money out.

Like it’s a laundry machine—you just throw it in and it comes out clean.

But markets don’t output answers.

They transform inputs—time, risk, behavior, luck—all moving at once.

The 10% is not a bond coupon. It’s a description of history, after the fact.

We do this with AI too. Prompt in. Answer out.

And it feels like the answer lives inside the system.

But it doesn’t.

It’s being generated, shaped, reweighted every time.

The system isn’t storing answers—it’s transforming inputs at light speed.

And transformation is harder to trust than retrieval.

Because it can surprise you.

That’s where the discomfort comes from.

Not math. Not money. Not AI.

But not knowing what question you’re really asking.

Because with any question, you can get a very precise answer.

4.89 is a perfect answer—to the square root of 24.

(And technically, it should be 4.9 if you round 4.898979…)

That’s risk.

Not that the system is broken.

But that it’s working exactly as designed—and you don’t realize it.

Magic is fun because you know there’s a trick.

Math and investing can be frustrating because you don’t know what’s driving the result. And in investing, edge doesn’t last long.

So you either trust the output.

Or you disengage from the process.

Sometimes, both feel easier than understanding the transformation.

But the transformation is the whole point.

My mom is learning how to create surprise.

How to guide attention.

How to make something feel impossible.

Math, does the opposite.

It takes that feeling and slowly removes it.

It relieves that anxiety.

Not by giving you answers—

but by showing you what’s happening in the middle.

Because once you see that, it stops feeling like magic.

And starts feeling like control.

You stop seeing numbers on a screen.

You see companies.

You see cash flows.

You see growth.

You see a square with sides of 5 and know it’s 25 without asking anything.

The calculator isn’t the problem.

The market isn’t the problem.

The model isn’t the problem.

The question is.

Ask the wrong one—and everything looks like magic.

My mom is learning how to create that feeling.

I’m still learning how to understand it.