Your Best Case Scenario

For most of my life, I’ve been wired to think in terms of the worst case scenario.

Before every big leap—moving to the U.S. to work with Disney, relocating to Singapore for Spotify—I would ask myself the same question: What’s the worst thing that could happen? And the answer was always grounding, almost comforting. If everything fell apart, I could just go home. Reset. Start again.

That mindset made me brave in a very specific way. It took the edge off risk. It gave me permission to try, because failure never felt final—just temporary, reversible. A safety net disguised as realism.

And for a long time, it worked. But something shifts when you enter your 30s. It’s no longer just about whether something might fail—it’s about what kind of life you’re building, and whether you’re aiming high enough while you’re at it.

A friend of mine, who’s currently writing a book, said something that stuck with me: “You’ve got to flip it. Think about the best case scenario.” At first, it sounded almost naive. Best case? Isn’t that how you set yourself up for disappointment? Isn’t it safer to stay anchored in reality, to manage expectations, to prepare for things going wrong?

But the more I sat with it, the more I realized: constantly focusing on the worst case doesn’t just protect you—it also limits you.

When you only ask yourself what could go wrong, you subconsciously build a life around avoiding pain. You optimize for safety, not for possibility. You make decisions that are rational, measured… but maybe also a little smaller than they could be.

Thinking about the best case scenario does something different.

It forces you to articulate what you actually want—beyond survival, beyond “it’ll be fine.” It pushes you to imagine a version of your life where things don’t just work out, but really work out. Where risks pay off. Where timing aligns. Where you’re not just okay—you’re fulfilled.

And that kind of thinking is uncomfortable in its own way. Because once you admit what the best case looks like, you can’t unsee it. You have to confront the gap between where you are and where you could be. You have to take your own ambitions seriously.

It’s easier, in some ways, to plan for failure than to plan for success.

But maybe the goal isn’t to abandon the worst case mindset entirely. It’s still useful. It still keeps you grounded, resilient, practical. Maybe the shift is about balance.

Yes, know that you’ll be okay if things don’t work out. Know that you can always go home, start over, rebuild. But also—give equal weight to the opposite.

What if this works better than you expected? What if this decision changes everything in the right way? What if the thing you’re hesitant about becomes the best thing that’s ever happened to you?

Your worst case scenario might keep you safe.

But your best case scenario? That’s what actually moves you forward.