Are You Too Careful?

I enjoy reading about someone who’s doing something I’m completely unqualified to do, or could ever imagine doing, to learn a thing or two that would benefit my life.

Here’s an example, and it’s happening currently on the game show Jeopardy. Do I watch Jeopardy? Nope, but I heard about it. Could I ever play Jeopardy? Not in a million years.

Contestant James Holzhauer, however, is on quite a winning streak. It’s possible that he has broken the game, nobody really knows. One thing is for sure — he seems unstoppable.

He’s efficient, too. At the time of this writing, his total winnings are over 1.6 million in 22 games and he’s still going. (Note: he’s on a two week break at the moment to allow for a regular Jeopardy competition.) For comparison, it took former record holder Ken Jennings 74 games to win $2.5 million.

What is it about Holzhauer that makes him so good at the game? Is it his knowledge? Is he fast on the buzzer? Or is his strategy what gives him the edge?

Of all those possibilities, what I”m most curious about is what he does that could help the rest of us.

Sure, Holzhauer is fast on the buzzer, and he’s super-knowledgeable, but so are other players who make it through Jeopardy’s pre-screening process.

So — is it his strategy that sets him apart?

Yes, in fact, he does a few things other Jeopardy players rarely do.

Name One.

He answers the hardest questions with the largest payoff first. He tackles the $1,000 categories and works his way down. Typically, contestants do the opposite.

In business coaching circles, this is known as “schedule the big rocks, don’t sort the gravel.” Important things, the big rock items, only get done if we, well, do them — if they’re our priority.

Holzhauer tackles the big rocks first.

What Else?

There’s more.

When he finds the Daily Double, he bets everything.

Explain, please.

For non-Jeopardy folks (I am one of those) there’s a square called The Daily Double and if you happen to land on it, it allows you to bet any part of your current winnings. Simple enough.

Typically, contestants are conservative about what they bet, but it turns out that Holzhauer is a professional sports better by day. He’s used to betting.

(Oh, that could explain a few things!)

He says, “The fact that I win and lose money all the time helps desensitize me, so I can write down $60,000 as the Final Jeopardy wager and not be trembling at the thought of losing that money.”

Further, his mindset is: “This isn’t a trivia question. It’s a coin flip that’s going to land heads for me a lot more often than it’s going to land tails, so I’m going to bet as much as I can on heads.”

You know, on that note, what if the rest of us rolled up our sleeves and took more chances during an average day? What if we said what we meant? Changed something about our daily routine that made a qualitative difference? What if we stood up for others more often, or for ourselves? What if we dropped a job we don’t enjoy, to go for something more soul-satisfying?

What if we threw caution to the wind and upped the ante where it matters, and we did it consistently — allowing us to develop confidence? What if, in the long run, regular practice would give us a stronger belief in how things naturally turn out well — often.

Developing natural confidence works entirely in our favor. Maybe it’s worth working on, worth practicing.

Anything Else?

Here comes a tricky one.

James cautions that to be successful, it’s important to to be comfortable.

He says, “Some of the opponents I’ve been playing, you can see they are visibly shaken by what’s going on onstage. Of course, you’re not going to play well if you’re up there trembling. And if you make yourself tremble by playing more aggressively than you are comfortable with, that’s so much the worse.”

Because James bets for a living, his comfort zone about taking chances is very different than the typical contestant, clearly a huge advantage for him.

And how does one get accustomed to taking risks? As we were just speaking about a moment ago — practice, practice, practice.

Drumroll, Please…

So here’s what we have so far.

Holzhauer tackles the hardest questions with the largest payoff first. He bets everything he’s got when given the chance. He practices winning and losing so that he’s comfortable with it. He believes things turn out well for him.

Now for the final idea.

When asked about his overall strategy, he said the traditional way of playing Jeopardy is too “risk-averse,” that what we often do doesn’t actually set us up to win.

He does what seems counter-intuitive. Each step of the way, he takes a risk that could throw him out of the game. He does the very thing that could cause him to lose.

And by doing this, he wins big, he wins often, and he wins fast.

James says,“Really, the big risk is never trying anything that looks like a big gamble.”

Why not take Holzhauer’s smackaroo advice into your week? Try new things and report back! I’d love to hear about it.

P.S. Photo credit goes to: Image by skeeze from Pixabay. Quotes from James are from

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Terri Crosby

Helping you create life-affirming, ever-evolving, happier relationships with those you love. Follow me on twitter at@TerriCrosby or read myblog.

Comments (2)

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    As a woman who has been called “risk averse” by her very astute son, I will tell you this article slammed my hand right into my forehead with a recognition of something I am struggling with today. So beautiful!!!!!!!!!


    • Avatar

      Terri Crosby


      Apparently, I wrote this blog for you! So grateful it hit home, and it helped.


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