James Holzhauer has been a Jeopardy phenomenon. Smart. Fast. Daring. Holzhauer's winnings of $2,462,216 in 32 games came within a hair of all-time champion Ken Jennings's $2.5 million total winnings over 74 straight games in 2004, only more than twice as fast.

As my Inc.com colleague, Jeff Haden, noted, Holzhauer avoided the common cognitive bias of "loss aversion" that would have capped his results at a much lower number. But he had one other strategic trick up his sleeve.

Notice that Holzhauer's average was more than double that of Jennings. That's because he had learned and embraced a brutal lesson that's a must for anyone who wants to succeed in business or life: Calculate your risk, and then go big. Keep it going even when you're terrified. If you succeed, you'll change the game altogether. But you'll have to recognize that one day the game will change, and then your strategy will need to change, too.

Find your swing-for-the-fences strategy

In life, many people follow the paths that others have cut. And that can work well enough. Those people may be satisfied and not want more. But if you're going to really break away, you need to find your own strategy and realize that it may sound crazy to many.

Holzhauer, a professional sports bettor, was impeccably prepared with his knowledge of trivia. But he changed Jeopardy, probably for however long it runs, as Oliver Roeder at FiveThirtyEight has explained. He went for high-dollar clues and pushed hard to find every Daily Double possible, then he bet big. The average bet on one of these clues was less than $2,500 since 2001. Holzhauer lifted that to almost $9,900.

He found that a combination of knowing probability (because bets are exactly that) and game theory (how to react in a situation given the way most people respond) supported his winning run.

What professional gamblers know about risk

Another thing Holzhauer did was stick with his strategy. As a professional gambler, he might have been used to how unnerving this could be, but it's absolutely critical. Managing your emotions is part of the professional gamblers' creed. Not that all strategies are worth using. Take the time to experiment to find a winning one. But once it's there, don't change it.

Holding on without flinching is tough. Even tougher is knowing when to change strategy. One reason Holzhauer was able to keep going was the amount of time it took for his opponents to change their playing style to match the new game Jeopardy had become.

"Many of my opponents played like I do, but I'm not sure they would have done so without provocation," Holzhauer told Roeder. "In a sense, I may have helped bring about my own downfall."

Holzhauer's right, in part. If others had kept to the more conservative way of playing, he'd likely have continued to play. Enough caught on to the shift and moved with it. Then it was a matter of making a mistake when someone with enough skill and knowledge could take advantage of it.

Even a strategic champion can make a mistake. But it doesn't mean everything is over. Things go on. Your new challenge becomes how to improve your execution as well as to take your strategy to the next level. 

Published on: Jun 3, 2019
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.