15 Mind-Warping Strategies from Ryan Holiday That Will Break Your Understanding of Power and Success

Fahri Karakas
3 min readOct 31, 2024
Photo by Felix Mittermeier on Unsplash

Ryan Holiday went from college dropout to world-renowned strategist by discovering how ancient wisdom creates modern advantages.

Here are his most radical and lesser-known insights.

1. The Strategic Vulnerability Protocol

Holiday’s most shocking discovery: Strategic vulnerability beats strategic strength.

The formula:
Strategic Power = (Perceived Weakness × Opponent Overconfidence) ÷ Ego

Historical proof:
- Sherman’s march to sea (appeared weak)
- Amazon’s early “losses” (appeared unsustainable)
- Jobs’ “failures” (appeared finished)

Modern application: Make your preparation look like weakness.

2. The Obstacle Multiplication Framework

Most counterintuitive finding: Bigger obstacles create bigger opportunities.

The method:
1. List your worst obstacles
2. Multiply each by 10
3. Design solution for 10x problem
4. Apply to original obstacle
5. Watch competitors struggle with basic version

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Fahri Karakas
Fahri Karakas

Written by Fahri Karakas

Associate Professor in Business & Leadership at University of East Anglia. Passionate about doodling, imagination, and creativity. Author of Self-Making Studio.