🌳 Why Imagining Failure Makes You Stronger (According to the Stoics)

Turn Anxiety Into Armor With This Counterintuitive Stoic Technique

Author

Jon High
March 24, 2025 • Estimated Reading Time: 4 minutes

đź’­ Quote of the Week

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He robs present ills of their power who has perceived their coming beforehand.

Seneca

This isn't just philosophical fluff—it's a mental superpower. Seneca discovered what modern psychology confirms: difficulties lose their emotional punch when we've rehearsed them. By facing potential disasters in advance, we strip them of their ability to wreck us. Not pessimism—just reality with a helmet on.

đź’ˇ Stoic Lesson of The Week

Picture this: Your team just got the green light on a major project. The room buzzes with excitement.

But instead of popping champagne, you ask: "Let's imagine this project has failed. What went wrong?"

Talk about killing the vibe, right?

Yet this exact exercise—the "premortem"—is now standard practice at companies from scrappy startups to Fortune 500 giants. The Stoics invented it thousands of years ago.

They called it premeditatio malorum—the premeditation of evils. While wellness culture insists we "manifest success," the Stoics took the counterintuitive approach.

The genius part? Mentally rehearsing setbacks doesn't make you more anxious—it makes you bulletproof against anxiety.

What's worse: imagining getting fired, or being completely blindsided by it? The anticipated punch rarely hurts as much as the one you never saw coming.

🎯 Your Action Plan

  • For new projects: Before starting, ask "If this crashes, what caused it?" Then build specific guardrails.

  • During your commute: Mentally rehearse how you'd handle your boss quitting or your presentation bombing.

  • For deadlines: Add 50% more time than you think you'll need—what would have been a stressor becomes part of the plan.

  • Try now: Think of your biggest current project. Visualize it failing. What specifically went wrong? What safeguards can you implement today?

đź“– Story Time

Picture Seneca—advisor to emperors and one of Rome's wealthiest men—lying on the hard floor of his villa, wrapped in a rough beggar's cloak, eating stale bread.

His friends thought he'd lost his mind. "Why would someone with your fortune choose to live like a pauper?"

"I'm rehearsing my worst fears," he explained, "so that I might never fear them."

Years later, when Emperor Nero demanded his suicide, witnesses were amazed by Seneca's calm. While others would have been shattered, Seneca faced his fate with remarkable composure.

His final moments weren't spent in panic—he used them comforting his grieving friends. The disaster he had mentally practiced had finally arrived, and having faced it in advance, he had robbed it of its power.

🤔 Takeaway

With proper anticipation, we can endure anything. The world might call you a pessimist, but it's far better to accept reality as it is than to be blindsided when things inevitably go sideways.

✍️ Journal Prompt of the Week

Run your own premortem: Choose an important upcoming project and answer:

  1. If this fails completely, what specifically went wrong?

  2. What early warning signs would indicate these problems?

  3. What steps can you take now to prevent each issue?

đź“š Worth Your Time