Finding My Stakes: Why I Needed to Risk Something

“If any of us weren’t here tomorrow, it wouldn’t matter to Google.”

I said this in a leadership meeting several years ago. It wasn’t cynicism—just an observation.

We started each meeting by sharing something personal, and that day, I spoke honestly: I was playing a game without real stakes.

Some people at the table dismissed my comment. Others told me later they felt the same way.

At the time, I didn’t know exactly what I wanted to do instead. But one thing was clear: I wanted to feel like my work actually mattered.

I know I’m not the only one who has felt this. Many have sensed it but struggled to put it into words—let alone take action. This post is for them.

How to Legally Own Another Person

Reading Nassim Nicholas Taleb’s Skin in the Game helped me articulate what I had been feeling. Taleb argues that having real stakes in your decisions—bearing the risk of failure—is the only way to create something meaningful.

Looking back at my career, I had very little risk:

• A stable job.
• A comfortable routine.
• A predictable path forward.

And that was the problem. It was all too safe.

Taleb’s book forced me to rethink how I had been operating. Was I actually making an impact, or was I just another well-compensated cog in a system that shielded me from real risk?

Life in the Simulation Machine

One of the ideas that stuck with me was Taleb’s criticism of the Intellectual Yet Idiot (IYI)—people who operate in theoretical worlds, detached from the real consequences of their decisions.

I had started to feel like one myself.

I had opinions, strategies, frameworks—but at the end of the day, if something failed, I wasn’t the one paying the price. My salary was the same, my lifestyle unaffected.

I was playing on easy mode.

It reminded me of another of Taleb’s arguments—“Life in the Simulation Machine.” If you’re always protected from loss, if you can theorize endlessly without real-world feedback, do you ever truly experience life?

I realized that the best decisions, the best learning, and the best personal growth come from actually having something on the line.

Wolves Among Dogs

Another concept that struck me was the difference between wolves and dogs.

Dogs trade freedom for comfort. They’re fed, they’re protected, and they don’t have to struggle.

Wolves live with real stakes every day. They risk hunger, they face danger—but they own their survival.

I had been a dog for most of my life. Well-fed, comfortable, and safe.

But this isn’t about saying wolves are better than dogs. It’s simply how I felt—like I was choosing comfort over risk, security over the unknown. And maybe sharing this experience can help someone else recognize their own feelings better.

Still, I couldn’t shake the feeling that I wanted to be a wolf.

Choosing Skin in the Game

In my early 40s, I realized I didn’t want to be an IYI or a dog anymore. I wasn’t looking for status or wealth—I was looking for something with real consequences.

That’s why I decided to take a shot at starting my own business. Not because it was the easy thing to do, but because it was the only way to know if I could actually build something that mattered.

Not because I wanted unlimited upside, but because I needed to feel the downside. To know that if I failed, it would actually mean something.

Feeling the Stakes Now

For the first time, we’re starting to feel the stakes as we actively build our business and put ourselves and our product out into the world.

• We’ve been making connections.
• We launched our website.
• We started our outreach.

A month from now, we will have either made tangible progress toward growing our business or gained valuable lessons to refine our approach. Maybe both.

And that’s the point.

This isn’t to knock working at a big company. I found it to be an enjoyable, essential and invaluable experience in many ways. Many continue to do meaningful work. But I still believe in what I also said that day in the meeting:

“The talent in this room could all go our separate ways and contribute more to the world.”

Some of us will make that leap. Some won’t.

But for those who feel the pull—who sense that they want more but aren’t sure what it looks like yet—just start.

You won’t have all the answers. You won't even have all the questions.

You don’t need them yet.