Why Do You Believe What You Believe?

My grandfather passed away a few years after I graduated from college.

He was one of the best people I’ve ever known. We were very close, and his death hit me hard. During his semi-retirement, I had lunch with him almost every week throughout the summers.

It didn’t matter which restaurant we chose. We’d walk through the door and people would immediately call out his name. He’d spend the next twenty minutes making his way around the room, shaking hands, telling stories, laughing, and asking people about their families.

People lit up around him.

I’m not sure what that quality is called, but he had it. He made people feel seen. For me, he was the guy I looked up to and the person I wanted to become.

A few days after his funeral, I was talking with a pastor who led a Bible study I once attended. I was trying to make sense of my grandfather’s death. He had been a lifelong Catholic, but I wasn’t sure he had ever done what many evangelical Christians would describe as “accepting Jesus as his personal savior.”

So I asked a simple question to the pastor.

“Would my grandfather be in heaven?”

The answer came quickly and confidently.

“No. He’s most likely in hell.”

At the time, the pastor and many people in my Bible study believed that a person needed to personally accept Jesus Christ as their savior to enter heaven. Being a good person or attending church wasn’t enough.

I was devastated.

I remember feeling confused, angry, and guilty all at the same time. If that was true, had I failed him somehow? Should I have had different conversations with him? Should I have done more?

What followed was probably the first time in my life that I seriously examined one of my own beliefs. Not because I wanted to, but because I felt compelled to. I started asking questions. Why did I believe this? Why did the minister believe it? What did other Christians believe? What did Catholics believe? Where did these beliefs come from?

The experience didn’t push me away from faith. If anything, it pushed me toward curiosity.

I didn’t know it at the time, but that moment would follow me everywhere. It showed up in how I thought about entrepreneurship, content creation, investing, and now artificial intelligence. Every time I found myself absolutely certain about something, I eventually came back to the same question:

Why do I believe that?

Is Religion a Choice?

A few weeks ago, I was having coffee with a friend and we started talking about religion.

We were discussing Christianity and Islam and how both continue to grow in different parts around the world. The deeper we went, the more obvious something became. For most people, religion is less a choice and more an inheritance.

Simply put, religion can act like a GPS. Historically speaking, if you’re born in Ohio, there is a good chance you’ll grow up Christian. If you’re born in Iraq, you’ll likely be Muslim. If you’re born in India, you’ll probably be Hindu. There are exceptions, but for most people, the beliefs they hold are heavily influenced by geography, family, and community.

That observation led me back to the same question I’ve been asking ever since my grandfather passed away.

How many of my beliefs did I actually choose?

Religion isn’t unique to this. We inherit assumptions about almost everything.

The Assumptions We Inherit

Growing up, entrepreneurship always seemed like a reasonable path. My parents owned a restaurant. My grandfather and uncle ran a funeral home. Building something of your own wasn’t unusual in my family.

Many of my friends grew up in a completely different environment. Their parents worked for companies. Their expectation was to graduate, get a good job, and build a successful career inside an organization.

Neither group was right or wrong. But they started from different assumptions.

I’ve seen the same thing happen with artificial intelligence.

A few years ago, I had a conversation with a successful marketer who told me there was no way AI would ever create content as well as a human being. I asked why. He said computers could never be as imaginative as people. It couldn’t reason like humans.

So I asked another question.

“Why do you believe that?”

The conversation didn’t go much further. The belief was strong, but the reasoning wasn’t.

To be fair, twenty years ago I probably would have said the exact same thing. If you had told me that software would someday write articles, create images, generate business ideas, and produce full-length movies, I would have scoffed at the idea.

Today, I believe something very different.

Not because someone convinced me. Because I spent time questioning the assumption. I’ve used the tools, tested them, talked with people building businesses around AI, and consumed more research on the topic than I care to admit.

My opinion changed because I became curious enough to investigate instead of defend.

That’s the pattern I’ve noticed over and over again. One person sees entrepreneurship as freedom. Another sees risk. One person sees AI as an opportunity. Another sees a threat.

Most of us don’t arrive at those beliefs through our own analysis. We inherit them. Then we spend years treating them like facts.

Whether we’re talking about religion, entrepreneurship, content creation, or AI, the biggest blind spots are often the assumptions we stopped questioning years ago.

Which is why I keep coming back to the same exercise.

My Favorite Question

I’ve discovered that curiosity doesn’t always change your beliefs. Sometimes it strengthens them. At least then they’re your beliefs.

Over the years, one question has helped me more than any other:

What would someone with the opposite viewpoint say?

If you can’t fairly explain the other side of an argument, belief, or opportunity, there’s a good chance you haven’t examined your own side deeply enough.

That question has challenged my thinking about faith, entrepreneurship, politics, content creation, investing, and artificial intelligence. More often than not, it leads me to a few others:

• What assumption am I treating as fact?
• Where did that belief come from?
• If I were starting from scratch today, would I believe the same thing?

The older I get, the less interested I am in having all the answers. I’m much more interested in understanding why I believe what I believe.

Because some of the biggest opportunities in life and business are hiding behind assumptions we’ve never thought to challenge.

And for me, it all started with one question:

Why do I believe that?

P.S.: ​A reminder that I’m giving away my book, Burn the Playbook, for free​. Please share it with a friend. I’m finding more and more parents are reading this and then sharing it with their kids.