Confront the ‘What Ifs’ with Stoic Fear-Setting Exercises

Hard - Requires significant effort Recommended

The Stoics taught the practice of premeditatio malorum—premeditation of evils. Seneca wrestled in his mind with shipwrecks, exile, and torture not to induce worry, but to tame surprise and steel himself. The modern entrepreneur Tim Ferriss revived this as “fear-setting,” laying out every nightmare scenario so its shadow no longer loomed.

Viktor Frankl, who survived the Nazi camps, spoke of an “existential vacuum” when people lost belief in meaning. He said that by imagining the worst, he surrendered its power, transforming fear into readiness. John D. Rockefeller asked himself “What if the oil fields ran out?” before every market panic, then built his empire by acting boldly.

Psychologists call this “inoculation”—gradual exposure to a feared stimulus until it loses potency. Defining nightmares shrinks their mysterious terror, and gives you a battle plan rather than a paralyzing spiral. In trials, executives who practice fear-setting make faster decisions and handle setbacks with greater resilience.

Take your toughest worry and map out every possible downside, assign realistic odds, then sketch how you’d handle each hit. This process disassembles the dread and builds a clear, personal roadmap so you can move forward boldly tomorrow.

What You'll Achieve

You’ll transform vague anxieties into actionable plans, boosting decision speed and reducing panic when setbacks occur.

Transform Dark Shadows into Light Facts

1

Write your worst-case scenarios

Spend ten minutes listing every possible negative outcome. Be as exhaustive as possible—detail exile, job loss, public embarrassment.

2

Estimate each outcome’s likelihood

For each scenario, give a percentage chance (1–100%). If you can’t guess, research historical or personal precedents for guidance.

3

Plan mitigation steps

Next to each scenario, jot one or two actions you would take if it happened. For serious threats, sketch a brief plan of resources and contacts to tap.

Reflection Questions

  • Which ‘what if’ scenarios scare me most, and why?
  • How likely is each worst-case outcome, realistically?
  • What’s my first mitigation step for the top three risks?

Personalization Tips

  • A creative professional lists the worst-case “rejection by all galleries,” then maps out affordable online showcases.
  • An athlete fears a career-ending injury, researches rehab stats, and texts a physical therapist to plan rehab.
  • A manager dreads a failed product launch, gives it a 20% chance, then drafts a backup marketing plan.
Courage Is Calling: Fortune Favors the Brave
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Courage Is Calling: Fortune Favors the Brave

Ryan Holiday 2021
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