The Lucky Ones: Is It Serendipity or Smarts?

June 15, 2007 — -- How lucky can you get? It turns out there's an answer to that question — and she's working behind the counter at a deli on Long Island.

Five years ago, Valerie Wilson won $1 million in a New York State scratch-off card game. Last year, she did it again, beating odds of more than 3 trillion to one. Is she the luckiest woman in America? "Well, I'll tell you what I say, 'Yes, I am,'" Wilson said with a laugh. "I was lucky as hell."

But when was the last time you heard a successful person call himself lucky? We'd all rather think of ourselves as hardworking or destined for success, not merely lucky.

"When something bad happens to you, it's bad luck," said "Freakonomics" author Stephen Dubner, summarizing today's prevailing attitudes. "When something good happens to you, it's your skill and hard work. It's pretty simple."

Fact is, we've changed how we feel about luck. Once calling someone lucky was a compliment. Now it sounds like a put-down. Consider this: In 1927, Charles Lindbergh flew across the Atlantic and was hailed in Paris as "Lucky" Lindy; 78 years later, Lance Armstrong won his seventh Tour de France and was also hailed in Paris, but after all his superhuman exertion on his bike, can you imagine calling him "Lucky" Lance?

Lucky Stars?

Bing Crosby was one of the consummate vocalists of the 20th century, yet the title of his autobiography was "Call Me Lucky." Back then, crediting luck was a familiar way for a show-business superstar to show modesty in the face of overwhelming success, as if to say, "This could've happened to anyone."

Now, even the most marginally talented entertainers seek to justify their time in the spotlight by citing their years of hard work and personal sacrifice, not just luck.

Consider, as few do these days, Kevin Federline, former consort to Britney Spears. She turned him from a backup dancer to a solo artist, but when asked what had led to his opportunity, he told Details magazine, "I've been dancing my a-- off since Fresno."

"We like to control our own fate, in general," Dubner said. "With luck, that's the thing you can't control, and I think that frightens people."

Lucky or Smart?

No one seems less likely to say he got lucky than successful businessmen. "Because it takes away from the brilliance of their accomplishments," said Bo Peabody, "and they don't want that."

Now a successful venture capitalist and restaurateur, Peabody has written a book entitled "Lucky or Smart?" about his days as the 20-year-old founder of a late 1990s Internet startup called Tripod that was bought by the search engine Lycos.

"It wasn't profitable at all," said Peabody. Yet in the dot-com frenzy of the era, Lycos paid $64 million for it. Was that being smart or was that being lucky?

"That was being lucky," he said. "There was no way that that company was worth $64 million."

It doesn't mean he didn't work hard or make good decisions along the way. He did. But Peabody knows there's a place for luck in the business world: "I was smart enough to realize I was getting lucky."

Few understand the interplay between luck and hard work like professional poker players, who can win and lose millions at the tables.

"There's not a professional poker player in the world that became a pro based on pure luck," said top pro Daniel Negreanu. "It has to be skill. On any given day, you could beat me at poker. But if we played twice, if we played 10 times, if we played 1,000 times, I would come out ahead — regardless of how much luck you have."

Playing the Odds

At the tables, he calculates odds, reads players' tendencies and draws on years of experience. So when he gets called "lucky," he knows what that means. "It's a way of insulting you, by saying it's not your skill that wins you, it's just that you're lucky," he said.

And yet Wilson says that for her customers, luck be a lady — herself. Her customers at the deli ask her to rub their lottery tickets on her body, in the hopes that some of her luck will rub off, too. She doesn't mind a bit. "Go ahead, take a piece, you know?"

But by month's end, luck won't live in that Long Island deli anymore. Wilson's moving to the country and quitting her job. Yet she won't quit buying scratch-offs, and counting on what so many of us these days want to deny or ignore: pure luck.

"Why should I stop now, just 'cause I won? Besides," she says with a wink, "maybe I'll win a third time!"