You are currently viewing Winning Jeopardy! Strategy could Help Freelancers Make More Money

Winning Jeopardy! Strategy could Help Freelancers Make More Money

Strangely, James Holzhauer’s winning Jeopardy! Strategy could help gig economy workers and freelancers make more money.

The controversial Holzhauer is “the man who broke Jeopardy!;” or a “quiz-show savant,” depending on which commentator you read. Jeopardy! purists loathe Holzhauer because he won around $1.7 million by breaking the iconic game show’s unwritten rules.

To clarify, Holzhauer bags single-game prize totals; like $110,914; on 9 April 2019, with a brilliant yet simple strategy. Incredibly, Holzhauer wins big by answering the toughest Jeopardy! questions first.

The Typical Jeopardy! Contestants’ Losing Strategy

To explain, Jeopardy! is a popular American quiz show; in which contestants use 30 clues producers array in a grid, to answer questions.

Moreover, the Jeopardy! producers place the hardest clues at the bottom of the grid. Historically, contestants answer the easiest questions first and move down the grid. Additionally, most contestants answer all the questions in one category before moving onto the next. Producers array the questions in categories to make questions easier to understand for viewers at home.

In fact, almost every Jeopardy! contestant has employed that strategy since the series began in 1964, Bill Rice Jr. notes at The American Conservative. However, there is no rule mandating that strategy’s use.

James Holzhauer’s winning Jeopardy! Strategy

Holzhauer; on the other hand, maximizes his winnings by concentrating on the toughest questions at the bottom of the board.

“And he goes all in as often as he can,”Wired culture writer Brian Barrett observes. “Holzhauer does not jog; he blitzes the bottom of the board, where the hardest and most valuable clues reside.”

Holzhauer goes straight to the bottom first because that is where the most valuable questions are. Effectively, Holzhauer concentrates his efforts where he can make the most money.

Why James Holzhauer wins at Jeopardy!

This strategy gives Holzhauer several decisive advantages over the typical Jeopardy! contestant. Here are the highlight’s of Holzhauer’s winning strategy:

First, Holzhauer tackles the hardest questions when he has the most energy. Thus, he is not as tired; or as confused, as some of his opponents. Plus, he can answer the easier questions when his energy levels are lower.

Second, by answering questions in different categories Holzhauer keeps his mind quick and agile. This gives Holzhauer a huge edge by forcing him to think creatively and remember quickly.

Third, Holzhauer gets more practice honing his skills at the tougher questions. Hence, he becomes a more effective player than his opponents.

Fourth, opponents have less opportunity to play the tough questions because Holzhauer gets them first. Fifth, the opponents are more tired because they are wasting their time with the chump change questions.

Sixth, opponents have less time because they are wasting their time with the easy stuff. Seventh, Holzhauer has more time to answer the tough questions. Eighth, Holzhauer’s habit of darting around the board befuddles his opponents.

All Holzhauer; a professional gambler, is doing is implementing basic strategy. On the other hand, most of the smart people who appear on Jeopardy! do not comprehend how the game works. Instead, the teachers, computer programmers, and college professors mindlessly follow the rules and make little money.

How James Holzhauer’s Jeopardy! Strategy can help you make more money

If you are a freelancer; or a gig-economy worker, you could make money with Holzhauer’s Jeopardy! Strategy. Lessons Holzhauer can teach freelancers include:

Concentrate your efforts on the highest-paying work. In particular, schedule the most lucrative jobs first and do them first. In fact, I advise freelancers not to start lower paying work until they complete the most lucrative gigs.

Ignore, low-paying work until you complete the higher-paying work. A good way to achieve this goal is to ignore low-pay clients until you get the better-paying stuff done.

Learn the rules of the game, and the system. For example, understand the rules by which gig-economy platforms like Upwork, Steam, Medium, Patreon, Lyft, and Uber operate.

Freelancers must think Strategically

Look for hacks and shortcuts. Effectively, Holzhauer is hacking Jeopardy! by exploiting its rules.

Study and think before doing. Instead of just doing the work, Holzhauer made a careful examination of Jeopardy! and devised a strategy for winning. He found the shortcuts by studying the game.

Think strategically, Holzhauer wins because he thinks strategically and understands strategy. Thus every gig economy worker and freelancer must learn strategy to make money.

Concentrate on the Big Money

Concentrate your efforts on the big goals. Most Jeopardy! Contestants win a pittance, because they concentrate on the low-paying questions. Conversely, Holzhauer makes far more money because he focuses on the high paying questions.

Most freelancers make the same mistakes as the average Jeopardy! contestant. For instance, your average freelancer completes jobs in the schedule they come in. Thus he or she postpones the big money for the little money. Typically, freelancers will not halt low-pay jobs when higher-paying work comes in.

An excellent application of this strategy is to work on the big or high-paying jobs first thing in the morning. I often complete or work on big work before checking email or social media. As a result, I complete the big work without distractions, when I am fresh and full of energy.

Unfortunately, many freelancers; and contractors, start their workday with email or social media. Starting with messages is a mistake, because needy clients, friends, family, etc., will distract you from the big money.

Moreover, many freelancers do not apply for higher-paying or more complex jobs. Hence, those workers get stuck in the grind of low-pay shit jobs and never make good money.

Understand Gamification and Game Theory

Finally, Holzhauer wins at Jeopardy! because he understands gamification and game theory. Game theory is the science of studying games, and gamification is the application of game theory to daily life.


You can apply game theory to freelancing by having a big goal; for instance attracting 100,000 views on Medium and working towards it each day. A related strategy is to hone and upgrade your skills by competing with the best, or taking the hardest jobs.

Interestingly, Holzhauer competes with the best; by answering the hardest questions on the board, first. You can achieve the same result by doing the hardest freelance work you can find, first.


Moreover, Holzhauer gives himself a strong incentive to work hard by concentrating on the highest-paying questions. He wins by raising the stakes, thus you can get better gigs by raising your stakes.

Games like Jeopardy!, are not life, but they can teach us a lot about life. In particular, games can teach you how to make more money at gigs and freelancing if you understand them.