1: George Washington, father of our country.  “Brave and bold general, towering over everything he surveyed, repelling the occupied and tyrannical British.”  

This image is the one most Americans hold of our First President, writes Ryan Holiday in The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

The reality is a bit less glorious but much more interesting.  

George “wasn’t a guerrilla, but he was close enough,” writes Ryan.  “He was wily, evasive, often refusing to battle.  His army was small, undertrained, undersupplied, and fragile.  He waged a war mostly of defense, deliberately avoiding large formations of British troops.  For all the rhetoric, most of his maneuvers were pinpricks against a stronger, bigger enemy.  Hit and run.  Stick and move.”

George’s military philosophy?  To avoid confronting the enemy where and when they expected to be attacked.  Instead, “Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success,” George said. 

He was more adept at “withdrawing than at advancing—skilled at saving troops that otherwise would have been lost in defeat,” Ryan writes.  He “rarely got trapped—he always had a way out.  Hoping simply to tire out his enemy, this evasiveness was a powerful weapon—though not necessarily a glamorous one.”

George was a master of misdirection.  “His most glorious ‘victory’ wasn’t even a direct battle with the British,” Ryan notes.  “Instead, Washington, nearly at the end of his rope, crossed the Delaware at dawn on Christmas Day to attack a group of sleeping German mercenaries who may or may not have been drunk.”  

2: The ability to be strategic about when and where to fight is often a key to success.  “The great myth of history, propagated by movies and stories and our own ignorance, is that wars are won and lost by two great armies going head-to-head in battle,” Ryan observes.

“It’s a dramatic, courageous notion—and also very, very wrong.”

The historian B. H. Liddell Hart studied more than 30 conflicts, including more than 280 campaigns from ancient to modern history.  His conclusion?  “In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army,” Ryan notes. 

Six.  As in 2 percent. 

Where, then, is victory found?  “From everywhere else,” writes Ryan.  “From the flanks.  From the unexpected.  From the psychological.  From drawing opponents out from their defenses.  From the untraditional.”  

Liddell writes in his masterwork Strategy: “[T]he Great Captain will take even the most hazardous indirect approach—if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications.  Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.”

3: The lesson for us?  Learn to ask: Is there a way to go around the problem?  To find some leverage.  Perhaps an indirect advantage.  

Which is contrary to our default setting when faced with a challenge.  “Is it to outspend the competition?  Argue with people in an attempt to change long-held opinions?  Are we trying barge through the front door?” Ryan asks.

“Because the back door, side doors, and windows may have been left open.”

Whatever it is we are doing, it’s likely to be more difficult to attack head-on, Ryan tells us.  When we’re starting at zero, taking on more established players who’ve built up their defenses, we aren’t likely to win playing to their strengths.  So, don’t.  Focus our precious resources elsewhere.

“As someone once put it after fighting Jigoro Kano, the legendary five-foot-tall founder of judo, ‘Trying to fight with Kano was like trying to fight with an empty jacket!'” writes Ryan.

That can be us.

We can remind ourselves of General Ulysses Grant bypassing Vicksburg to capture it.  Or, “think of Hall of Fame coach Phil Jackson and his famous triangle offense, which is designed to automatically route the basketball away from defensive pressure rather than attack it directly,” Ryan writes. 

We can avoid wasting our time and energy in conflict driven by ego and pride.  

“Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages,” Ryan observes.  “They can be gifts.  Assets that make us less likely to commit suicide with a head-to-head attack.  These things force us to be creative, find workarounds, sublimate the ego, and do anything to win besides challenging our enemies where they are strongest.  These are the signs that tell us to approach from an oblique angle.”

The other advantage to this mindset?

“People or companies who have that size advantage never really have to learn the process when they’ve been able to coast on brute force,” Ryan notes.  “And that works for them . . . until it doesn’t.”


Reflection: What is a challenge I am currently facing?  Is there a way around the problem?  A way to find some hidden leverage or indirect advantage?

Action: Experiment with this approach and pay attention to and reflect on what happens.

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