The cucumber is bitter? Then throw it out.
There are brambles in the path? Then go around.
That’s all you need to know.
In 1915, deep in the jungles of South America, the rising conflict between two rival American fruit
companies came to a head. Each desperately wanted to acquire the same five thousand acres of
The issue? Two different locals claimed to own the deed to the plantation. In the no-man’s-land
between Honduras and Guatemala, neither company was able to tell who was the rightful owner so
they could buy it from them.
How they each responded to this problem was defined by their company’s organization and
ethos. One company was big and powerful, the other crafty and cunning. The first, one of the most
powerful corporations in the United States: United Fruit. The second, a small upstart owned by
To solve the problem, United Fruit dispatched a team of high-powered lawyers. They set out in
search of every file and scrap of paper in the country, ready to pay whatever it cost to win. Money,
time, and resources were no object.
Zemurray, the tiny, uneducated competitor, was outmatched, right? He couldn’t play their game.
So he didn’t. Flexible, fluid, and defiant, he just met separately with both of the supposed owners
and bought the land from each of them. He paid twice, sure, but it was over. The land was his.
Forget the rule book, settle the issue.
This is pragmatism embodied. Don’t worry about the “right” way, worry about the right way. This
is how we get things done.
Zemurray always treated obstacles this way. Told he couldn’t build a bridge he needed across the
Utila River—because government officials had been bribed by competitors to make bridges illegal—
Zemurray had his engineers build two long piers instead. And in between which reached out far into
the center of the river, they strung a temporary pontoon that could be assembled and deployed to
connect them in a matter of hours. Railroads ran down each side of the riverbank, going in opposite
direction. When United Fruit complained, Zemurray laughed and replied: “Why, that’s no bridge.
It’s just a couple of little old wharfs.”
Sometimes you do it this way. Sometimes that way. Not deploying the tactics you learned in
school but adapting them to fit each and every situation. Any way that works—that’s the motto.
We spend a lot of time thinking about how things are supposed to be, or what the rules say we
should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are
right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making
due with what we’ve got. On focusing on results instead of pretty methods.
As they say in Brazilian jujitsu, it doesn’t matter how you get your opponents to the ground, after
all, only that you take them down.
What Zemurray never lost sight of was the mission: getting bananas across the river. Whether it
was a bridge or two piers with a dock in the middle, it didn’t matter so long as it got the cargo
where it needed to go. When he wanted to plant bananas on a particular plantation, it wasn’t
important to find the rightful owner of the land—it was to become the rightful owner.
You’ve got your mission, whatever it is. To accomplish it, like the rest of us you’re in the pinch
between the way you wish things were and the way they actually are (which always seem to be a
disaster). How far are you willing to go? What are you willing to do about it?
Scratch the complaining. No waffling. No submitting to powerlessness or fear. You can’t just run
home to Mommy. How are you going to solve this problem? How are you going to get around the
rules that hold you back?
Maybe you’ll need to be a little more cunning or conniving than feels comfortable. Sometimes
that requires ignoring some outdated regulations or asking for forgiveness from management later
rather than for permission (which would be denied) right now. But if you’ve got an important
mission, all that matters is that you accomplish it.
At twenty-one, Richard Wright was not the world-famous author he would eventually be. But poor
and black, he decided he would read and no one could stop him. Did he storm the library and make
a scene? No, not in the Jim Crow South he didn’t. Instead, he forged a note that said, “Dear Madam:
Will you please let this nigger boy have some books by HL Mencken?” (because no one would write
that about themselves, right?), and checked them out with a stolen library card, pretending they
were for someone else.
With the stakes this high, you better be willing to bend the rules or do something desperate or
crazy. To thumb your nose at the authorities and say: What? This is not a bridge. I don’t know what
you’re talking about. Or, in some cases, giving the middle finger to the people trying to hold you
down and blowing right through their evil, disgusting rules.
Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to
point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so
many of us spend so much time looking for the perfect solution that we pass up what’s right in front
As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.”
The Stoics had their own reminder: “Don’t go expecting Plato’s Republic.”
Because you’re never going to find that kind of perfection. Instead, do the best with what you’ve
got. Not that pragmatism is inherently at odds with idealism or pushing the ball forward. The first
iPhone was revolutionary, but it still shipped without a copy-and-paste feature or a handful of other
features Apple would have liked to have included. Steve Jobs, the supposed perfectionist, knew that
at some point, you have to compromise. What mattered was that you got it done and it worked.
Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also
imminently practical and guided by the possible. Not on everything you would like to have, not on
changing the world right at this moment, but ambitious enough to get everything you need. Don’t
think small, but make the distinction between the critical and the extra.
Think progress, not perfection.
Under this kind of force, obstacles break apart. They have no choice. Since you’re going around
them or making them irrelevant, there is nothing for them to resist.
Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse.
The popular image of George Washington in American lore is of a brave and bold general,
towering over everything he surveyed, repelling the occupied and tyrannical British. Of course,
the true picture is a little less glorious. Washington wasn’t a guerrilla, but he was close enough. 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.
Never attack where it is obvious, Washington told his men. Don’t attack as the enemy would
expect, he explained, instead, “Where little danger is apprehended, the more the enemy will be
unprepared and consequently there is the fairest prospect of success.” He had a powerful sense of
which minor skirmishes would feel and look like major victories.
His most glorious “victory” wasn’t even a direct battle with the British. 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.
He was actually better at withdrawing than at advancing—skilled at saving troops that otherwise
would have been lost in defeat. Washington 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
It’s not surprising then, as the general of the Continental Army and the country’s first president,
that his legacy has been whitewashed and embellished a little. And he’s not the only general we’ve
done it for. 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. It’s a dramatic,
courageous notion—but also very, very wrong.
In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern
history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In
only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main
Only six. That’s 2 percent.
If not from pitched battles, where do we find victory?
From everywhere else. From the flanks. From the unexpected. From the psychological. From
drawing opponents out from their defenses. From the untraditional. From anything but . . .
As Hart 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.
When you’re at your wit’s end, straining and straining with all your might, when people tell you
you look like you might pop a vein . . .
Take a step back, then go around the problem. Find some leverage. Approach from what is called
the “line of least expectation.”
What’s your first instinct when faced with a challenge? Is it to outspend the competition? Argue
with people in an attempt to change long-held opinions? Are you trying to barge through the front
door? Because the back door, side doors, and windows may have been left wide open.
Whatever you’re doing, it’s going to be harder (to say nothing of impossible) if your plan includes
defying physics or logic. Instead, think of Grant realizing he had to bypass Vicksburg—not go at it—
in order to capture it. 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.
If we’re starting from scratch and the established players have had time to build up their
defenses, there is just no way we are going to beat them on their strengths. So it’s smarter to not
even try, but instead focus our limited resources elsewhere.
Part of the reason why a certain skill often seems so effortless for great masters is not just
because they’ve mastered the process—they really are doing less than the rest of us who don’t
know any better. They choose to exert only calculated force where it will be effective, rather than
straining and struggling with pointless attrition tactics.
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!”
That can be you.
Being outnumbered, coming from behind, being low on funds, these don’t have to be
disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-tohead
attack. These things force us to be creative, to find workarounds, to 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.
In fact, having the advantage of size or strength or power is often the birthing ground for true
and fatal weakness. The inertia of success makes it much harder to truly develop good technique.
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. And that works for them . . . until it doesn’t. Until they
meet you and you make quick work of them with deft and oblique maneuvers, when you refuse to
face them in the one setting they know: head-to-head.
We’re in the game of little defeating big. Therefore, Force can’t try to match Force.
Of course, when pushed, the natural instinct is always to push back. But martial arts teach us
that we have to ignore this impulse. We can’t push back, we have to pull until opponents lose their
balance. Then we make our move.
The art of the side-door strategy is a vast, creative space. And it is by no means limited to war,
business, or sales.
The great philosopher Søren Kierkegaard rarely sought to convince people directly from a
position of authority. Instead of lecturing, he practiced a method he called “indirect
communication.” Kierkegaard would write under pseudonyms, where each fake personality would
embody a different platform or perspective—writing multiple times on the same subject from
multiple angles to convey his point emotionally and dramatically. He would rarely tell the reader
“do this” or “think that.” Instead he would show new ways of looking at or understanding the world.
You don’t convince people by challenging their longest and most firmly held opinions. You find
common ground and work from there. Or you look for leverage to make them listen. Or you create
an alterative with so much support from other people that the opposition voluntarily abandons its
views and joins your camp.
The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a
shortcut or fighting unfairly. There’s a lot of pressure to try to match people move for move, as if
sticking with what works for you is somehow cheating. Let me save you the guilt and selfflagellation:
You’re acting like a real strategist. You aren’t just throwing your weight around and hoping it
works. You’re not wasting your energy in battles driven by ego and pride rather than tactical
Believe it or not, this is the hard way. That’s why it works.
Remember, sometimes the longest way around is the shortest way home.