We’ve noted before that the lucky,  as a breed, tend to be pessimistic. They certainly don’t fit the image suggested by the funny old phrase “happy-go-lucky.” That phrase conjures up a picture of a breezily optimistic, carefree man or woman who never worries about bad outcomes. The paradoxical fact is that such people, despite their cheery smiles and sunny dispositions, usually lead unlucky lives.

Optimism means expecting the best, but good luck involves knowing how you will handle the worst.

Entering any new situation – a job, a personal relationship, a money venture – the lucky person applies the First Technique. He or she makes a clear distinction between planning and luck: “This situation is only partly under my control. Good or bad luck – events not of my making – could make it ripen into something good or could make it go sour.” Having fixed that in mind, the lucky individual then applies a worst-case analysis.

“I know this situation can go wrong. Now I’ve got to ask how it can go wrong. What is the worst possible outcome? Of if there are two or more ‘worst’ outcomes, what are they? How can it go wrongest? And if the worst does happen, what will I do to save myself?”

That is the opposite of being happy-go-lucky.

Margaret Farrar was among the very luckiest of all he people I’ve ever interviewed, and she owed a good deal of her stunning success to the fact that she was a dedicated worst-case analyst. Let’s take a look at her long, happy life.

She lived in the world of crossword puzzles, and for many years she was its undisputed queen. She all but invented crosswords as we now know them, worked for 27 years as crossword editor of The New York Times, and turned out a fabulously profitable series of puzzle books for Simon and Schuster. But the likelihood is that we would not know her name today if she had not applied this Eighth Technique at least twice in her lucky career.

I went to see in 1979. She lived in a large, old, book-cluttered apartment on New York’s Upper East Side. She met me at the door: a small, trim woman of 82 with a brisk, friendly manner. I had not come to interview her specifically on the subject of luck, but I knew immediately that I was in the presence of a consistently lucky personality. After she had given me a cup of coffee, she began to tell me her life story with these words: “Succeeding at anything isn’t just a matter of being smart, you know. You’ve got to be lucky too.” (That was the First Technique in action.) “I’ve always been lucky. It started when I was a young woman. I always seemed to be in the right places at the right times.”

Margaret Farrar – then known either by her maiden name, Petherbridge, or her nickname, Piff – turned up in New York in 1921. After bouncing around a bit, she found a job as secretary to the Sunday editor of the old New York World.

The World had recently begun publishing what it called “word cross puzzles” to fill space. These were uninteresting little diamond-shaped constructions containing no words longer than six letters .Neither the editors nor the readers had much enthusiasm for them. They were regarded as mere space fillers and that attitude showed. The puzzles were marred by errors, made-up words such as “xinx” (defined as “sound made by falling coins”), dull definitions, and a general lack of pride and care.

The job of producing the weekly puzzle was assigned to junior staff members, none of whom wanted it. Each would perform the task ill-temperedly for a few weeks, then think of a reason why it should be dumped into the lap of someone else. Finally, it was Piff Petherbridge’s turn.

When an editor asked her to take on the job, her first reaction was delight. She guessed – more correctly than she knew, as it turned out – that a piece of unexpected good luck had come blundering into her life. “I saw it as a way to escape the secretary trap,” she recalled. “In those days, secretarial jobs trapped most women all through their working lives. If you were a woman and you got a chance to do something else, anything else, you went for it.”

But when that first surge of euphoria subsided, young Piff applied the indispensable Eighth Technique. She asked what could go wrong, and a very gloomy scenario presented itself to her. She saw herself devoting full time to the puzzle in order to improve it. The improvements would happen slowly. The general lack of enthusiasm would remain. Finally, the editors would decide to abandon the puzzle. Piff would want to return to her secretarial job, but somebody else would be filling it. And so Piff would find herself out on the sidewalk.

That was the worst case as she imagined it. She made her worries known to an editor, who laughed and said she was inventing nightmares. Nonetheless, she insisted on extracting a promise form the editor. The promise was that the World would continue publishing the puzzles for at least a year no matter what happened.

If young Piff had not applied this worst-case analysis and arranged protection for herself, it is conceivable that crossword puzzle as we know them today would not exist.

She began her new assignment with high enthusiasm. She expanded the puzzle’s size so as to offer more challenge for literate readers. She tightened the rules under which the puzzles were constructed. She discouraged use of unfamiliar words such as “fiber of the gomuti palm” (which had appeared in the first puzzle the World ever published) where a more common word could be substituted with a little thought. She discouraged other lazy  tricks such as making up a word like “xinx”. She also tightened the editing and proofreading so as to eliminate misspellings, definitions keyed with the wrong numbers, and other errors. And she paid special attention to the patterns of blacked-out squares. She established rules that have since become gospel in American puzzledom (though not in England): The pattern must have an eye-pleasing symmetry; every letter must be part of two words; and so on.

But, as she had foreseen in her worst-case scenario there was no instant surge of enthusiasm for the puzzles. Some of the newspaper’s top editors decided that “word cross puzzles” were never going to be of any help in building circulation. They wanted to abandon the puzzles.

But Piff Petherbridge held them to their promise: one year. As it turned out that gave her just enough time. By the end of the year, reader’s enthusiasm had risen just enough to persuade the editors that they should continue publishing puzzles for another few months. And so the young puzzle editor’s lifelong enterprise was saved.

In time, the crosswords become one of the World’s most popular daily features. Piffy’s tiny empire grew when two young assistant editors joined her.

Then, in 1924, crossword puzzles suddenly became a national craze. It came about when two smiling young men were escorted to Miss Petherbridge’s desk. Their names were Richard Simon and Max Schuster. They had a harebrained scheme in mind. They wanted to start a publishing company, and they thought they would like to launch the venture by publishing a book of crossword puzzles. They wanted the World’s puzzle editor and her assistants to put the book together.

The newspaper’s top columnist, Franklin P. Adams, advised her not to touch the scheme with a ten -foot pole. It couldn’t succeed, he said. Crossword puzzles were an esoteric pastime for a very small, select group of quirkily literate people. To hope that a puzzle book would appeal to a mass market was ridiculous.

But the fledging firm of Simon and Schuster was offering the puzzle editors $25 apiece to assemble the proposed boo. Piff could think of many good uses for $25. Moreover, when she subjected the situation to worst-case analysis, it did not look very bad. “Suppose the book failed,” said said, explaining her reasoning. “Suppose it failed miserably. What would I lose? My good name? But I really had very little of a name to lose at that point.”

She decided the situation was much like that of entering a lottery. The risk of losing was large, but the amount to be lost was small. Just in case the book did succeed, she negotiated a contract under which she would share in the financial rewards through royalties.

She and her assistants began to assemble the book. But now a different “worst-case” presented itself to her. Suppose the manuscript got lost?

Some World editors ridiculed this private nightmare of hers, but she had thought about it carefully. What started her worrying about it was a steady ebbing of enthusiasm for the book. There had never been high enthusiasm to begin with, but even that modest allotment was diminishing. Franklin P. Adams had refused to write a foreword. So had several other prominent literary folk, including the well known editor and literary critic, John Farrar. Faced with this repeated rejection Simon and Schuster were beginning to have second thoughts. Maybe a crossword book wasn’t such a good idea after all.

Piff sensed that it would take only one more misfortune to induce them to abandon the project. It wouldn’t have to be a major misfortune. Any minor stroke of bad luck would do. One possible stroke of bad luck, as she analyzed it, could be the loss of the manuscript.

If she lost it, she could reconstruct it, but that might take a month or two. She would then fail to meet Simon and Schuster’s deadline. That failure, added to the continuing decline of general enthusiasm, might bring on the death of the project. She could hear Simon saying to Schuster, “You mean we’ve got to wait two more months for this book? Listen, maybe this is a blessing in disguise. I’ve been thinking for a long time that we ought to talk this over.” And she could hear Shuster saying to Simon, “Well, yes, since you mention it, I’ve been having some second thoughts myself.”

When she asked them directly if they were losing enthusiasm, they tried to assure her they were not. She strongly suspected that was only a kindhearted lie. She became sure of it when they announced a change of plan. Instead of issuing the book under the name they had originally chosen for their company, Simon and Schuster, they planned to dissociate themselves from possible failure by hiding under name Plaza Publishing.

This piece of news intensified Piff’s worries about losing the manuscript. There were no copying machines in those days; and while carbon paper was available, few newspaper people ever used it. As a result, there was only one complete copy for the crossword book. The three editors added to it piece by piece, sometimes taking parts of it home, often leaving it lying about on desks and file cabinets. There were too may ways in which all or part of it could get lost. Piff spent two weekends making a complete copy by hand.

And just as she had foreseen in her worst-case scenario, the original manuscript got lost. Somebody left it in a cab. Since the publishers’ deadline was only a week or two away, that could have been the end of the project. Also the end of Piff’s bright and lucky future. But she had taken steps to save herself. She turned in the duplicate manuscript. And, thus, she preserved the good luck that might otherwise have fluttered out of her grasp.

The book was published on April  10, 1924. Price $1.35, including a pencil, an eraser, and a postcard that could be mailed to Plaza Publishing for a set of puzzle solutions.

The first printing was a timid and pessimistic 3,600 copies. To everybody’s surprise, it sold instantly. Something about crossword puzzles seemed to have touched an American nerve. A second printing also sold out. So did a third and large printing, and so did a series of progressively bigger ones, up to an eighth, ninth, and tenth of 25,000 copies each. Before the astounding and cross-mad year was over, two more puzzle books had been rushed into print. On a single day during the Christmas shopping season, some 150,000 wee sold.

Piff Petherbridge was rich. She was soon to marry the contrite literary critic who had refused to write a foreword for her first book, and as Margaret Farrar she would quickly become famous throughout the English-speaking world. When Webster’s New International Dictionary installed the phrase “crossword puzzle” as a regular listing for the first time in 1934, Margaret Farrar was asked for a ruling on whether or not the spelling should include a hyphen.  When The New York Times instituted the first Sunday Puzzle in 1942, she was hired as editor, and she oversaw the inauguration of the first daily puzzle in 1950. She was the queen of crossword puzzledom and remained queen throughout her life.

“I wasn’t unusually clever or unusually anything.” She would say. “I was just lucky.” Exactly. Composing and editing crossword puzzles requires a high degree of literacy and a lot of patience, but there are thousands of people who are abundantly supplied with these good qualities. Margaret Farrar became the ruler of puzzledom because she was in the right place at the right time – and because, at least twice, she applied the Eighth Technique.

She asked what the worst outcome could be and prepared herself to handle it. If she had been happy-go-lucky instead, her great luck would not have happened.

We are now in a position to ask a question that has baffled amateur gamblers for centuries:

Why do professionals usually win?

“Because they cheat,” is the cliche reply, but the truth is that professionals – meaning men and women who earn all or a substantial part of their income by gambling – are far less likely to cheat than amateurs are. Cheating would be foolish for a pro. The pro doesn’t need to take that extra risk.

Professional gambler win because they reject optimism. They apply the Fifth Technique: the trick of selecting luck, of abandoning any venture rapidly when it turns sour. And they apply the Eighth Technique: the trick of worst-case analysis.

The amateur gambler hopes or prays the cards will fall his way. That is optimism, and it doesn’t win card games. The pro, by contrast, studies how he will save himself when the cards fall against him.

That is the single most important reason why pros almost always go home with more money in their pockets than amateurs do. And it is the same on Wall Street .If you analyze the differences between consistent winners and losers in that greatest of all gambling casinos, one difference stands out starkly: The losers are optimistic.

The New York Times once sent a reporter around to interview a commodities speculator named Martin Schwartz, a consistent winner who in one year increased his fortune by a spectacular 175%. Asked how, Schwartz said succinctly, “I learned how to lose.”