Embrace rare events to thrive on chance

Hard - Requires significant effort Recommended

No one saw the 2008 meltdown coming—trillions evaporated overnight, and even the brightest economists were blindsided. Meanwhile Netflix quietly tested streaming in 2007. That tiny experiment gave it a decades-long head start.

These are Black Swans: extreme surprises that fundamentally reshape the landscape. Some sting, some soar—but by definition, they lie outside everyday forecasts.

Why do we miss them? Because our brains crave stable patterns. We build models for linear growth, then mutter “should have seen it” when the curve explodes or collapses. Yet in reality, non-linear jumps are common—in technology adoption, viral trends or supply shocks.

The key isn’t predicting each one; it’s placing a few strategic bets and guarding against the worst. Keep most resources in steady assets, but reserve a tiny share for improbable gambles. Then stress-test both sides of the wager. You’ll sleep better knowing one small wildcard can transform your future—or avert disaster.

Black Swans demand paradoxical planning: expect the unexpected by preparing for extremes, not just averages.

You can’t forecast Black Swans, but you can profit—or at least survive—when they strike. First, jot down the few one-in-a-hundred events that could sink you, from market crashes to unexpected laws. Next, seed a tiny sliver of your resources into upside bets that would skyrocket if they pay off. Finally, run extreme “what if?” drills for each scenario and draft rapid-response playbooks. This two-pronged approach lets you sleep easy: you’re ready to thrive on surprise rather than dread it.

What You'll Achieve

You’ll shift from fear-based planning to a balanced portfolio of safety and opportunity, positioning yourself to survive shocks and capture windfalls.

Build your Black Swan strategy

1

List high-impact risks

Brainstorm the one-in-a-hundred events that could sink your plan—market crashes, supply chain failures, sudden regulation.

2

Design optional upside bets

Allocate a tiny portion of resources to moonshot ideas that could multiply your gains, like new markets or breakthrough tech.

3

Stress-test your model

Run ‘what-if’ scenarios for each Black Swan—ask “What if revenue doubles? Or plummets?”—and draft rapid response checklists.

Reflection Questions

  • What single extreme event could ruin my current plans?
  • Which unlikely bet could multiply my result tenfold?
  • How would I react if that scenario materialised tomorrow?

Personalization Tips

  • Investing: buy a small ticker-ticker option on an emerging biotech firm while keeping most funds in low-volatility bonds.
  • Career: spend a weekend building a blog or side gig that could become a six-figure platform.
  • Product: test an unconventional feature in your app with 1% of users—you’ll spot sudden hits before competitors.
The Art of Thinking Clearly
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The Art of Thinking Clearly

Rolf Dobelli 2011
Insight 7 of 7

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