Let’s Talk Worst-Case Scenarios

So, you’re considering starting your own business, but fear is creeping in. You’re asking yourself: “What if it doesn’t work?”

Well, let’s break it down. What’s the absolute worst-case scenario? Your business fails, and you go back to a 9-to-5? If that’s your current reality, then your worst-case is literally just life as it is right now. Let that sink in.

Now, of course, I’m not saying to jump in recklessly. You should absolutely consider your own circumstances, have a plan, and move strategically. But take a step back and seriously ask yourself: What do I actually have to lose?

For me, the upside was unlimited. And in my first few months of business, I landed deals that I wouldn’t have even thought were possible when I started. The kind of deals that made me realize just how much I had been limiting myself by staying in a comfortable but unfulfilling job.

But honestly? My biggest fear wasn’t failure. It was that when I did finally start my own business, I would be more successful than I had imagined—and I’d regret not betting on myself sooner.

Reading Thinking in Bets by Annie Duke completely shifted my perception of risk and decision-making. It made me realize that every choice we make is a bet on the future—there are no guarantees, only probabilities. The smartest move isn’t to wait for certainty, but to make calculated bets based on the best information available. And when I looked at starting my business through that lens, the decision became clear: the potential upside far outweighed the risk.

We often overestimate the risk of failure and underestimate the potential for success. The truth is, the biggest risk isn’t losing—it’s never trying at all.

So instead of letting fear hold you back, compare your best-case vs. worst-case scenario side by side. If your biggest fear is ending up right where you started, maybe the real risk is staying there forever. 🚀