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Jeff Bezos’ Rule: Stop Overestimating Risk and Underestimating Opportunity
- Startup Bell
- Mar 3
- 3 min read
What stops most people from chasing big ideas? Fear of risk.
Jeff Bezos, the founder of Amazon, believes that human nature is wired to overestimate risk and underestimate opportunity. And that’s precisely why so many people never take the leap—they convince themselves the downsides are bigger than they actually are, while failing to see how massive the upside could be.
“The risks are probably not as big as you perceive, and the opportunities may be bigger than you perceive.”
This mindset isn't just for entrepreneurs—it's for anyone looking to make bold moves, take chances, and build something great.
Photo: Getty Images
The Risk Is Rarely as Big as You Think
Imagine it’s the late 1990s. You’re sitting in a comfortable, high-paying job at a hedge fund. Life is stable. Your career is set. Would you leave all that behind to sell books on the internet?
Most people wouldn’t.
But Jeff Bezos did. He saw something that others didn’t: the opportunity was bigger than the risk.
Everyone around him thought starting an online bookstore was crazy—the internet was new, bookstores were already everywhere, and e-commerce was barely a thing. But Bezos challenged his fear of failure with a simple question:
"What’s the worst that could happen?"
The answer? If Amazon failed, he could always get another job. The downside wasn’t catastrophic. But the upside? Potentially unlimited.
Most people do the opposite. They imagine every way things could go wrong, but fail to see the ways things could go incredibly right.
The Myth of “Playing It Safe”
Let’s flip the script for a moment. What if Bezos had stayed at his hedge fund? He would have had a steady paycheck, sure. But he would have also missed out on building one of the most successful companies in history.
That’s the real risk—wasting your potential because you’re too afraid to take the first step.
Bezos isn’t saying risk doesn’t exist—he’s saying that we often make it out to be bigger than it is. When we zoom out and look at the bigger picture, we realize that staying still is often riskier than moving forward.
“Thinking small is a self-fulfilling prophecy.”
If you think small, you’ll act small. If you act small, you’ll never create something big.
Bias Yourself Toward Action
Bezos suggests that instead of getting paralyzed by risk, entrepreneurs (and ambitious people in general) should bias themselves against this natural fear.
How do you do this?
1️⃣ Ask yourself: "What’s the worst that could happen?"
Can you recover if things don’t work out? (Most of the time, the answer is yes.)
2️⃣ Flip the risk: "What happens if I don’t do this?"
Are you missing out on something bigger by playing it safe?
3️⃣ Bet on yourself.
The people who make an impact aren’t the ones who wait for the perfect moment. They take the leap and figure it out along the way.
Final Thought: Don’t Let Fear Kill Opportunity
If you’ve been sitting on an idea, waiting for the "right time," or convincing yourself it’s too risky—take a second look. You might be overestimating the danger and underestimating the reward.
The biggest breakthroughs don’t come from playing it safe. They come from people who see opportunities where others see obstacles.
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