Lose to Win

An essay on the virtues of defeat. From Yacht Racing, March 1972
sailboat racing illustration
The guy who regularly beats you has served his apprenticeship of defeats and is now reaping the benefits. Sailing World Archives/Mark Smith

Let those who consistently sail to victory remain smug and not read this article, lest they see herein the future and be touched with the first gentle pangs of anxiety over their eventual defeat by that newcomer who now just barely muddles around the course. Winning sailors don’t lose their touch, they just get out of the habit of learning from every race. Those of us who are losing have the decided advantage of being hungry for victory and thus learn something from every loss.

After a year of watching the rest of the fleet sail gracefully off into the distance, the act of gradually improving to the point of being able to sail around several marks with your competitors brings one to a peak of ecstasy that will probably never be experienced again in sailing, except perhaps when one first rounds the windward mark in the lead.

Therein lies the advantage of the novice, and the reason why this sage of 29 years asserts loudly for all the world to hear—today’s losers shall inherit tomorrow’s trophies, for the pains of defeat provide more incen­tive to win then do the joys of victory.


Losing a sailboat race is probably one of the most distressing conditions in which a person voluntarily puts oneself. What could be more simple, on first sight, than speedily and easily sailing around those little marks?

Almost anyone can learn to sail within a matter of hours. In fact, if we are to be truthful with ourselves, we are forced to admit that sailing is ludicrously easy after a bit of practice.

If sailing is so easy, why then is competitive sailing so agonizingly difficult? During our first races as a beginner, why are we only one third of the way to the mark when everyone else is rounding? Or, why is our boat continually alternating between luffing and almost capsizing when everyone else is merrily beating into a 15-knot hurricane, with smiles on their faces and joy in their hearts? On light air days, how are they able to plod cheerfully onward while our tub wanders resolutely back from whence it came whenever a wave of more than two inches in height breaks apathetically under the bow? With the same sails and boat, how come other guy sails higher and faster than we do on the beats, and even faster on the reaches and runs?


The answer to such questions lies in the acquisition of a sound psychological understanding of the sailboat and the relationship of the helmsman to it.

And the key to this understanding (and to the secret of eventual success) lies in the recognition of our boat’s inherent devilishness, with which we must constantly battle and from which we can constantly learn.

Scientific knowledge to the contrary, who can privately doubt that the tender, hypersensitive creature we allegedly command actually has an inhumanly human and maliciously independent spirit of her own? To those rationalists who scoff and claim otherwise, I say this: explain in 25 words or less why changing the length of the forestay by three inches puts you far ahead this week and at the back of the fleet the next, under the same wind conditions.


Love her if you will, be obsessed with the joy of flying with her as I am; but recognize for the sake of your mental well-being that she is a stubbornly contrary mistress who hungers not for victory but rather for the thrill of helping you do the wrong thing whenever possible. She thirsts for the embarrassment of defeat. She tosses her head high and laughs aloud as you sail her on her side in heavy weather while your competitors stay flat and fast. She cries with exultation as you learn the improper methods of jibing, filling her to the thwarts in the process. She gurgles with pleasure as you sit back and drag her stern on the runs. She shivers her jib with delight as you pinch more and more while your competitors move further and further ahead. And who else but she would chuckle and chatter when you reach down into a hole while everyone else goes high and sails off into the sunset?

She wants to lose. She goes out of her way to help you lose.

But therein lies her virtue and the moral of this little tale. The old cliché about winning races by making the fewest mistakes is not only trite, but true. And how do we learn to make the fewest mistakes? By making mistakes. Nobody learns to cover until he loses because of his failure to cover. We learn how to round properly by rounding wrongly and losing. We learn how to tune for and sail the beats by getting angry enough to find out everything we can about the subject and then getting out and tuning and practicing and racing and racing and racing.


There are no child prodigies or other amazing successes in sailboat racing. The dozens (or hundreds) of variables in tuning, tactics, boat handling and wind­finding see to that. The guy who regularly beats you has served his apprenticeship of defeats and is now reaping the benefits. He got there as a result of a lengthy quest for ways to avoid the embarrassment and agony of defeat.

Our helpful friends tell us to win by thinking we are going to win. Fine advice if you are already an expert, but not very practical if you’re still struggling to stay in sight of the fleet. I contend that the road to victory lies in thinking that you’re not going to get beaten as badly this week as you did last week (and re­doubling your energies when you do get even more thoroughly trounced).

Narrowing the gap by persisting in the face of defeat, and learning from each defeat, is the true victory. And not only does such persistence lead to eventual trophies, but it creates untold anxiety in the minds of those who are currently at the top of the heap. Nothing is more frightening to a victor than the loser who hangs on and keeps coming back for more, and who keeps getting closer and closer in the process. It’s enough to take the joy out of victory and put it in defeat.