The Flank Attack
When the direct path is blocked, find the indirect route to victory
Holiday draws on the military historian B.H. Liddell Hart's study of 280 campaigns across history, which found that only 2 percent of decisive victories came from direct frontal attacks on the enemy's main army. The other 98 percent came from indirect approaches -- flanking maneuvers, surprise attacks, asymmetric strategies. Holiday applies this insight to all obstacles.
When you cannot overcome an obstacle head-on, you must find an indirect route. George Washington won the American Revolution not through decisive pitched battles but through evasion, hit-and-run tactics, and attacking when least expected -- famously crossing the Delaware on Christmas Day to surprise sleeping mercenaries. He was better at strategic withdrawal than at direct engagement.
The flank attack also applies to using obstacles against themselves. Gandhi didn't fight the British Empire directly; he provoked them into displaying their own tyranny. Martin Luther King Jr. met physical force with soul force, exposing violence as indefensible. In judo and jiu-jitsu, you use the opponent's momentum and strength against them rather than meeting force with force.
- Direct frontal attacks on strong opponents almost never succeed; indirect routes win nearly all decisive victories.
- Persistence and evasion compound into eventual advantage when direct force is unavailable.
- The strategic withdrawal is not defeat; it is preparation for the asymmetric strike.
- Provoking a stronger opponent into exposing their own weakness is a form of indirect attack.
- When you cannot match your opponent's strength, make your battlefield one where their strength does not apply.
- Assess Whether the Direct Path Is ViableBefore committing to a frontal assault on your obstacle, honestly evaluate whether you have the resources, strength, and positioning to overcome it directly. If the odds are heavily against you or you lack a critical advantage, the direct approach will likely fail. Recognize this without ego.
- Study the Obstacle for WeaknessesEvery obstacle has structural vulnerabilities. Look for the places where it is overextended, complacent, or rigid. Ask where the obstacle least expects resistance. Look for what the obstacle takes for granted. Washington noted that where little danger is apprehended, the prospect of success is fairest.
- Design an Indirect ApproachCraft a strategy that avoids the obstacle's strengths and targets its weaknesses. This may mean attacking from a completely unexpected direction, withdrawing to draw the obstacle toward you, using its own energy against it (as in jiu-jitsu), or redefining the terms of engagement entirely. Be creative -- the indirect path is limited only by imagination.
- Execute with CommitmentIndirect strategies require full commitment to be effective. Half-hearted flanking is worse than a direct attack because it exposes you without delivering a decisive blow. Once you choose the indirect route, pursue it with complete dedication and speed.
- Be Ready to AdaptIndirect approaches often unfold in unexpected ways. Maintain flexibility and be prepared to pivot as the situation develops. The advantage of indirect strategies is that they keep you nimble -- preserve that advantage by not becoming rigid in your execution.
Washington's Continental Army was undersized, undertrained, and undersupplied compared to the British. Rather than engaging in large-scale pitched battles, Washington waged a war of evasion, hit-and-run attacks, and strategic withdrawals. His most famous victory came from crossing the Delaware on Christmas Day to attack sleeping mercenaries -- not a direct engagement with the main British force.
Holiday draws on the military historian B.H. Liddell Hart's study of 280 campaigns across history, which found that only 2 percent of decisive victories came from direct frontal attacks on the enemy's main army. The other 98 percent came from indirect approaches -- flanking maneuvers, surprise attacks, asymmetric strategies. Holiday applies this insight to all obstacles.
When you cannot overcome an obstacle head-on, you must find an indirect route. George Washington won the American Revolution