What If It Goes Better Than Expected?

You know that voice in your head? The one that kicks in the moment you’re about to make a big decision?

“What if I embarrass myself? What if I can’t afford this mistake? What if i fail?”

Yes, that one. We all have it. As humans, we’re basically professional catastrophizers—it’s how we have survived as a species. But here’s the thing: when you’re a founder or an executive making decisions that matter, that voice will eventually become your worst enemy.

I see this all the time with my clients. Brilliant leaders who can spot market opportunities from miles away, but when it comes to their own next move? Suddenly they’re paralyzed by every possible way things could go sideways.

I get it because I lived it too many times to count.

Last year, I was staring down one of those crossroads moments. I’d just left my role at Slack/Salesforce to go all-in on coaching. Then—plot twist!—my wife and I found out we were expecting our third child.

After the initial wave of excitement wore off, the mental spiral followed: How am I going to support another kid on an uncertain income? Can I really build this business while being present for my family? Did I just make the biggest mistake of my career?

For weeks, I was stuck in worst-case-scenario mode. Until one day, almost by accident, I asked myself a different question:

What if it goes better than expected?

I know, I know… it sounds almost too simple. But here’s what happened when I actually sat with that question…

Instead of picturing financial ruin, I started imagining what it would look like to build a business on my terms. Instead of worrying about being an absent father, I began to see how being my own boss might actually make me more present. Instead of fearing the unknown, I became excited about the possibilities I couldn’t even see yet.

Fast forward to today: I’m holding my three-month-old daughter as I write this. And you know what? All those fears I had? They never materialized. In fact, the opposite happened. I’m more focused, more energized, and more driven than I’ve ever been—both as a business owner and as a dad.

I’m not saying you should ignore real risks or skip the planning phases. Smart leaders always have contingencies. But if you’re only planning for what could go wrong, I promise you’re missing half the equation.

The breakthrough moments, the unexpected opportunities, the doors that open when you least expect them—none of it shows up in your risk analysis spreadsheet.

So next time you’re facing a big decision (or even a small interaction you’re not looking forward to) and that familiar voice starts listing all the ways you could fail, try this…

Give it a minute to be heard. The voice is trying to protect you after all. You can even thank it! Then ask yourself:

What if it goes better than expected?

You might be surprised by what you discover.