Is the glass half full or half empty?

I can see an argument for both.

If you think it's half full, I hate to break it to you: the half empty guys are almost always right.

What?

Let's take a step back. What do "half full" and "half empty" mean?

Traditionally, the idea of a glass being half full or half empty is a litmus test for whether someone is optimistic or not.

  • If you think the glass is half full, you're an optimist
  • If you think the glass is half empty, you're a pessimist

So why are pessimists on the winning side?

Well actually, they're not.

Even though pessimists are usually correct, they're the ones who end up losing.

Optimists, though typically incorrect, are the ones who win.

In this letter, I'm going to show you why optimists win—and why being wrong most of the time is the whole point.

Pessimism is in your blood

Take yourself back to hunter-gatherer times and imagine this scenario:

Two of your ancestors are foraging for food in the savanna.

They're walking and going about their day when they both hear a rustle in the tall grass nearby that stops them dead in their tracks. They look over to where they heard the sound and instantly spot it:

A lion.

The first hunter, the optimist, whispers to his friend:

"That lion doesn't see us. Come on, let's walk past it and get to our usual hunting spot."

The second hunter, the pessimist, whispers back:

"No, that lion definitely saw us. I'm turning around."

They agree to disagree, and part ways. The optimist continues forward and the pessimist returns home.

Can you guess what happens next?

If you guessed that one optimist was removed from the human gene pool that day (thanks to a particularly hungry lion), then you'd be right.

You descend from pessimists. It's the reason you're alive today.

There are no lions anymore

When's the last time you saw a lion?

Years ago, I'm guessing? Probably during your last trip to the zoo?

The threat of lions eating us is virtually nonexistent now. And that's a big problem.

Because we all have pessimism genes in us. Some of us are more optimistic than others, sure. But as the story of the two hunters shows, the pessimist was rewarded handsomely for being doubtful.

He was rewarded with his life.

There's a clash between our pessimist genes and the environment around us.

Though there are no lions around to eat us, we still worry about them. But we don't worry about literal lions eyeing us up as their next meal.

Instead, these "lions" manifest as more subtle threats in the modern world:

  • losing your job
  • failing your startup
  • missing your mortgage payment

But none of these "lions" are as dangerous as real lions.

Will losing your job, failing a business, or missing one mortgage payment directly and immediately cause you to die?

No! Of course not.

And those elaborate threat chains we make in our heads when stressed out, like "if I forget a pencil for school, I'll fail my math exam, if I fail my math exam, I won't go to college, if I don't go to college, I won't get a job, if I don't get a job, I will die" are just vestigial structures of our pessimist genes.

As a result of our pessimist genes, we end up being much more risk-averse than we need to be.

We imagine that there are lions everywhere hiding in the grass, ready to eat us.

In reality, there are just a few bees flying around that can sting but have no potential to kill us.

Why being wrong is awesome

I love being wrong.

And I mean that. Let me explain.

Earlier, I mentioned how pessimists are usually correct.

Think about how many predictions they make that are right:

  • "That business is going to fail" (most of them do)
  • "That relationship isn't going to last" (most don't)
  • "Elon Musk is going to miss that deadline he set (he usually does)

In fact, it's pretty easy to make predictions that are right.

You just need to be doubtful of positive, order-creating outcomes and due to the nature of the universe being entropic, you'll typically be right.

But there's a catch to being right (almost) all the time.

Ask yourself this:

Are the pessimists taking action?

Is the pessimist opening that bakery that she's always dreamed of owning as a child? Is the pessimist launching that mobile app that she always felt like was missing from people's lives? Is the pessimist asking out the person she's had a crush on for years?

No, I don't think so.

The catch to being a pessimist is you don't take action that moves you from zero to one. Action that creates value. Action that creates something, out of nothing.

The only way to get those zero to one opportunities is to be an optimist.

To bet on yourself.

To believe that it is possible—despite what all the doubters around you are saying.

And that means you'll be wrong. A lot.

You're going to make many mistakes along the way.

But that's okay.

Because the best prize of being an optimist isn't getting a massive multimillion-dollar exit from selling your media company, fulfilling your childhood dreams of experiencing zero gravity, or even finding your soulmate.

The best prize of being an optimist is living a life that you won't regret.

Pessimists win arguments. Optimists win outcomes.
Pessimists are right 99% of the time, but wrong 100% of the time.

Last Update: May 24, 2026