Why We Always Overestimate Enemies Until We Count Them

Medium - Requires some preparation Recommended

Early in his career, Ulysses S. Grant found himself alone, short on supplies, and convinced a nearby wolf pack would devour him. He and a fellow officer tip-toed through tall prairie grass, hearts pounding. In the dim light, every rustle sounded like a dozen snarling animals. Grant admitted later he froze at the imagined pack of twenty wolves.

When they finally stumbled upon the source—just two wolves lounging in the clearing—Grant learned a lasting lesson: we routinely multiply dangers in our mind. Decades later, as commander of Union forces, he repeated that story to rally troops against overwhelming odds, reminding them there are always “more of them before they are counted.”

That moment taught Grant—and can teach us—all to ground our fears in reality. When you line up real numbers against imagined ones, your next move becomes clear. The enemy vanishes under the light of accurate headcounts.

Pull out your notebook or phone and list what feels like a mountain of obstacles, then fact-check each one with data or a quick conversation. Note how your imagined enemy shrinks when you face actual numbers. Let that clarity propel you into action tomorrow.

What You'll Achieve

You’ll replace exaggerated worries with an accurate risk map, reducing overwhelm and giving you the confidence to move forward.

Count Your ‘Wolves’ to Tame Them

1

List the threats you imagine

Spend 5 minutes writing every challenge you think stands in your way, from coworkers who might disagree to tasks you dread.

2

Verify the count

For each item, look for concrete proof. Ask a colleague to rate how serious each obstacle really is—focus on facts, not feelings.

3

Reassess your mindset

Compare your original list to your verified list. Notice where you inflated numbers or seriousness. Journal how this shifts your confidence.

Reflection Questions

  • Which fears on my list were based on gut feelings rather than facts?
  • How did verifying real data shift my willingness to act?
  • What’s one next step now that the obstacles seem manageable?

Personalization Tips

  • A startup founder lists “ten competitors” only to discover two actual rivals.
  • A parent worried about ten ways their teen might rebel finds just one real friction point.
  • A student imagining dozens of interview questions narrows it to five core topics.
Courage Is Calling: Fortune Favors the Brave
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Courage Is Calling: Fortune Favors the Brave

Ryan Holiday 2021
Insight 3 of 8

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