There isn't a single decision you get to make about your life and career that isn't somewhat of a gamble.
Whether you make the decision or not, you're gambling on a potential win or a loss.
You might think saying no protects you from risk, but what you forget is that not deciding is its own gamble. By avoiding the choice, you could be steering yourself straight into the wrong outcome.
When I accepted a role in Dubai and moved my family across the world, it looked like a reckless gamble to everyone else. Friends and colleagues asked me again and again, "Why are you doing this?" To them, the risk was in saying yes. To me, the risk was in staying put. After six years at Zillow, my career had stalled, and holding on felt like betting on the wrong horse. Rolling the dice on something bold felt safer than gambling on being stuck.
That's the part most people miss. The risk isn't always in saying yes. The risk can be in saying no. The risk can also be in sitting on your hands and convincing yourself that standing still is safe.
We tell ourselves stories that inaction is neutral. That waiting is wise. That we are just "being careful." But waiting is a gamble in itself. You're betting on timing to deliver clarity. You're betting that the perfect moment will show up without you moving. You're betting on luck without putting chips on the table.
The truth is, inaction is one of the riskiest bets of all. When you delay the decision, you don't freeze the outcome. You just let time decide for you. And time is a terrible decision-maker.
Every yes carries risk. Every no carries risk. Every delay carries risk. There is no safe box you get to sit in where life pauses until you're ready. The world keeps moving, with or without your participation.
So the real question is not whether you want to gamble, but how. Do you gamble on staying comfortable and hoping it will all work out? Do you gamble on saying no and watching opportunities pass you by? Or do you gamble on saying yes, stepping forward, and giving yourself the chance to grow into something bigger than where you are today?
The people who get ahead are not the ones who avoid gambling. They are the ones who understand that life itself is a series of wagers. They push their chips in, even when they don't know exactly how the cards will fall. They gamble on themselves, again and again.
What feels like the riskiest gamble might just be the safest one long term. Staying still might feel safe, but it is the bet most likely to backfire. Betting on yourself, even if you fall short, is the only gamble that guarantees you learn, grow, and move forward.
So the next time you're hesitating, remember this: you're already gambling. The question is whether you're betting on fear, or betting on yourself.