The greatest “winners” are almost always the greatest losers as well. Here’s why…


I have some good and bad news. Which would you like first?

If you’re like me, you prefer your medicine before your dessert, so here’s the bad news:

In the struggles of life, you’re going to be the loser sometimes.

You’re not going to win every battle. Someone is going to outsmart you. You’re going to get blindsided by the unforeseeable. An obstacle is going to prove much more formidable than you had anticipated.

But remember this: just because you lost a battle doesn’t mean you’ve lost the war. (Click here to tweet this!)

In fact, the art of losing battles is just as important as the art of winning them. Sometimes a skillful defeat is the difference between the prelude to a powerful counterattack and a catastrophic disintegration of the entire campaign.

An unskilled loser makes for an easy opponent. He loses focus and leaves his flanks wide open to be exploited. He goes down without a fight, letting you inflict massive damage with impunity. He fails to learn from his missteps and can be easily led into other traps and pitfalls.

On the other hand, a skilled loser is always a threat. He’s the worst type of opponent. He makes you scratch and claw for every inch of his territory. He might be down, but so long as he draws breath, he’s never out. He learns, adapts, and strikes back.

The point is this: if we want to win wars, we’d better know how to lose battles. And war analogies aside, this concept applies to any and all competitive endeavors, even those that only involve competing against the nebulous “marketplace” or even yourself; the “war” is the big goal and the “battles” are the milestones that must be realized.

So let’s look at what skillful losing looks like and how we can use it to improve our chances of ultimate success.

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1. Never lose because you got out-worked.

Nobody is easier to beat than the sucker that wastes time chasing after shortcuts, “weird tricks,” and other ways to avoid the real effort it takes to win.

Lazy people are ineffective and easily overcome. If you’re going to be a contender in any field, you simply can’t afford laziness.

Extraordinary diligence is a type of weapon in itself. It challenges would-be opponents to an arms race of sorts and saves you from having to deal with the riffraff that couldn’t hope to keep up.

A willingness to out-work demands respect. For the weak-willed, it’s intimidating and even discouraging to face. It instills a haunting dread that no matter how hard they’re working, it’s not going to be enough. Somehow, they figure, you’re going to be ahead.

The greatest generals in history were known for their almost superhuman ability to out-work their enemies.

For example, Alexander the Great was renowned for his unequaled dedication to his conquests. Once he locked his sights on the next milestone in his epic journey, whether it be the next city to subdue or next region to assimilate, he spent every waking minute in action, making it so.

In his own words, the most slavish thing was to “luxuriate,” whereas the most royal thing was to “labor.”

Napoleon also embraced this type of tireless work ethic. To prepare for his first major military conquest, he disappeared into his office for several days with massive maps of Germany, Switzerland, and Italy spread from wall to wall on the floor. On his desks were piles of reconnaissance reports and in boxes were stacked hundreds of note cards with possible moves the Austrians might make in response to the maneuvers he was planning.

He ran through every permutation of attack and counterattack imaginable and used this exhaustive analysis to build campaigns so finely calibrated that he was able to uncannily–and ultimately accurately–predict the towns where final battles would take place and even the diplomatic concessions that would be granted to him as a result.

The point is much of mystique enjoyed by winners is nothing more than an aura cultivated through the dint of long hours and hard work. (Click here to tweet this!) This is a power any one of us can immediately wield in our lives.

2. If you’re going down, go down fighting.

Sometimes it becomes clear that victory is no longer possible. And once defeat is inevitable, it’s almost always better to go down swinging. Do everything you can to deprive your opponent of an easy, painless victory.

This has several distinct advantages over crumpling into a ball and taking a beating: it helps you lose on a high note, it rallies you for the next fight, and it can inflict more damage than the winner expects, tainting the success with Pyrrhic overtones.

Robert Green spoke about this concept in his fantastic book The 33 Strategies of War:

“At the Battle of the Alamo in 1836, every last American fighting the Mexican army died— but they died heroically, refusing to surrender. The battle became a rallying cry— ‘Remember the Alamo!’— and an inspired American force under Sam Houston finally defeated the Mexicans for good. You do not have to experience physical martyrdom, but a display of heroism and energy makes defeat into a moral victory that will soon enough translate into a concrete one.

“Planting the seeds of future victory in present defeat is strategic brilliance of the highest order.”

(Click here to tweet this!)

Fortunately for most of us, we’re not fighting actual wars. Losing a battle doesn’t mean losing our lives.

But it can mean losing our self-respect and will to press on, and by “going down fighting”–by staying on track and seeing the losing battle through to a proper end–we can maintain our dignity, momentum, and morale. 

Remember that an effective counterattack is more powerful than an attack, but it requires a strong finish and transition into the next initiative.

3. Learn from your losses.

In defeat, the habitual loser does anything but carefully and objectively analyze it: he places blame elsewhere, revises the facts, or simply blocks it from his memory.

He also finds even the smallest failures incredibly demotivating because, going back to point number one, he’s looking for the free ride. He’s hoping it’ll all come easily. That it won’t cost too much sweat, time, or tears.

Don’t be this person.

Defeats can be remarkably instructive if you’re willing to take personal responsibility for your failures. (Click here to tweet this!) When you lose, assume it’s because you were beaten–that you just weren’t good enough. Try to find out why and how you could have done better.

Let your struggles and mistakes point the way. Here we can take a page from the book of top-tier professional sports players, many of whom rigorously and scientifically analyze every aspect of their games to pinpoint weaknesses they can strengthen through diligent, deliberate practice.

Military history is replete with examples of how patient, stubborn analysis of defeats can create breakthroughs that turn the tables.

For example, after several catastrophic defeats, the Romans realized they couldn’t beat Hannibal in large-scale, set-piece battles, so they devised an attritional strategy of scorched earth tactics and guerrilla warfare. Slowly but surely they ground Hannibal’s men and materiel down until he was no longer a threat to Rome.

Winners know that defeats don’t have to remain tragedies. They can be incredibly instructive and often show the way to future successes.


What do you think about the art of losing like a winner? Have anything else to share? Let me know in the comments below!