The Problem with Being 100% Sure

​Dave Chappelle’s latest Netflix special​ has me pondering some big questions. ​Along with his new purpose to say certain things to certain people​, he mentioned that he’ll listen to a lot of people, from many different perspectives, except for the ones who are 100% certain about something. When someone is absolutely sure, that’s when he starts to wonder if something might be wrong.

That idea stayed with me. It felt true. The people I trust most are rarely the ones who are completely certain. They’re usually the ones still asking questions.

When Certainty Pushes People Away

That thought took me back years earlier, to my time at Bowling Green State University. I was part of a wonderful faith-based organization while I was there. It meant a lot to me at the time. I had a long conversation one day with a pastor who was trying to convince me that humans lived at the same time as dinosaurs.

He wasn’t offering it as a theory or a question worth exploring. He was completely sure.

What made that conversation difficult wasn’t faith itself. In fact, part of me admired the confidence behind it. I was even a little envious of that level of certainty. But what bothered me was the absence of questioning. There was no room for curiosity, no willingness to examine evidence, no space to say, “I might be wrong” or “this is what I believe.” It was “this is the only truth.”

Ironically, that certainty ended up pushing me away from an organization I otherwise respected deeply. Not because I rejected belief, but because I struggled with belief that refused to question itself.

Why Absolute Certainty Makes Me Pause

Over time, I’ve noticed this pattern repeat itself in many areas of life. Religion. Politics. Culture. Even business. The louder and more absolute the certainty, the less curious the conversation becomes.

That concerns me.

When someone speaks with total certainty, I don’t immediately assume they’re wrong. But I do slow down. I ask more questions. I listen more carefully. And I remind myself that history is full of people who were absolutely sure and absolutely mistaken.

People were certain the Earth was flat. Certain the sun revolved around us. Certain disease had nothing to do with germs.

And today, there are people who are certain artificial intelligence will either solve everything or destroy everything. No uncertainty. No middle ground. Just confidence.

In every era, certainty feels logical and responsible…right up until it doesn’t.

Where I’ve Been Too Certain

I’ve done this myself.

Years ago, I was very confident that the platform didn’t matter for content creators. My belief was simple. If you focused on building owned media…email subscribers, direct relationships, assets you controlled…everything else would take care of itself. Platforms were just distribution. Sometimes temporary. Often replaceable.

I still believe deeply in ownership. That hasn’t changed.

What has changed is my certainty about how little platforms matter.

I underestimated how powerful discovery systems would remain. I didn’t fully appreciate how much algorithms would shape who even gets the chance to build an owned audience in the first place. Ignoring platforms entirely isn’t realistic for most creators today, and pretending otherwise doesn’t make it true.

My earlier certainty made the framework cleaner. It also made it less accurate.

That doesn’t mean the original idea was wrong. It means it needed curiosity to evolve.

Curiosity as a Human Instinct

One of the things I’ve always believed is that curiosity is one of the most remarkable qualities human beings possess. If you believe in God, you might even see curiosity as part of the design. The impulse to ask questions, to explore, to wonder how things work.

Progress doesn’t come from certainty. It comes from inquiry.

Certainty, when taken too far, shuts that instinct down. It replaces exploration with defense. It turns conversations into declarations.

A family member recently brought up the book ​Chariots of the Gods by Erich von Däniken​. The idea is that ancient civilizations may have been influenced by extraterrestrial visitors. I don’t know if that’s true. I’m skeptical. But what I appreciate about the book isn’t the conclusion. It’s the posture.

The author isn’t saying, “This is definitely what happened.” He’s saying, “What if?” He’s asking questions and inviting readers to think.

You can believe the theory is wrong. You can believe it’s impossible. But engaging with the question isn’t dangerous. Refusing to ask it might be.

“I Don’t Know” as a Practice

As we moved into 2026, I found myself thinking about resolutions. Like most people, I have the usual list. Eating better. Working out differently. Spending more time with friends and family.

But the resolution I care about most isn’t physical or financial. It’s intellectual.

I’m trying to say “I don’t know” more often.

For the first few weeks of the year, I’ve made it my default response when I’m unsure. Not as a conversation stopper, but as an opening. “I don’t know” creates space. It lowers defenses. It invites exploration instead of debate.

I’m beginning to believe that “I don’t know” might be one of the most honest answers we have.

Being willing to admit uncertainty doesn’t mean you lack conviction. It means you value learning more than being right. It means you’re open to updating your thinking when new information appears.

Holding Beliefs Lightly

The people I admire most aren’t the ones with perfectly formed opinions on everything. They’re the ones who are comfortable living with unanswered questions. They hold beliefs, but they hold them lightly. They listen. They adjust. They stay curious.

Absolute certainty can feel strong, but it’s often brittle. Curiosity, on the other hand, requires confidence. It takes courage to say, “I might be wrong.”

So when I hear someone speak with total certainty, I don’t immediately assume they’re wrong. But I do pay closer attention. And I remind myself that history doesn’t reward those who were most sure. It rewards those who stayed open.

Because the older I get, the more convinced I am of this.

If you’re 100% sure, that might be the problem.