Aaron Judge Bet on Himself and Gained $150M. You Too Can Win Big Like Judge with These 4 Tips.

Published in

Kenneth Flakes Professional Plus

4 min readDec 14, 2022

Source Keith Allison | Wikimedia Commons

This season Aaron Judge bet big on himself, and his huge gamble paid off greatly. In Judge’s “walk year”, the year immediately before becoming a free agent in baseball, he declined a seven-year, $213.5M contract extension from the New York Yankees before the first game of the season.

Judge then played the rest of the season without a new contract and proceeded to have arguably one of the top 20 offensive seasons in Major League Baseball history. Among his notable accomplishments, Judge:

Batted .311 and led the American League in home runs (62) and runs batted in (131)
Set an American League hoke run record, breaking a record held by Roger Maris for 61 seasons
Was named American League Most Valuable Player

Judge’s season was so memorable and historical that he was named Time Magazine’s Athlete of the Year. As a result of Judge’s historic season, he eventually signed a nine-year, $360M contract extension which makes his annual salary the largest for any positional player in baseball.

Many athletes could have simply chosen to accept the contract offered by the Yankees before the season began. At the time Judge had only earned just over $36M total in his career, but his gamble paid off enormously with a nearly 70% increase in contract value.

Although it may not seem like regular working professionals may have much in common with Aaron Judge’s contract situation, the truth is that many working professionals reach points in their careers where they may benefit from betting on themselves. Oftentimes workers must ask the following questions:

Should I bet on myself and…….

Chase a risky opportunity elsewhere
Take a stretch assignment at work
Switch careers
Pursue a passion project
Become a solopreneur or entrepreneur
Leave the country for work

Given that regular professionals often must decide to bet on themselves at some point in their careers, it is useful to have some strategies for preparing to make a bet yourself. Below are four tips that may be helpful:

1. Be confident

If you aren’t confident in yourself, then why would anyone else have any confidence in you? You are your biggest advocate, and your self-advocacy can lead to greater success for you when you bet on yourself.

2. Know your worth

You are more likely to bet on yourself if you know that you bring value to your organization. There are several ways to identify your worth at your job. For example, do you provide a skill or talent to your group or company that no one else can provide? If so, is this skill or talent something that would be valued outside of your company?

Also, talk to individuals that you trust and get honest feedback from them about your talents. This may help you assess your worth.

3. Study your peers

There is a lot of literature that claims that you shouldn’t compare yourself to your colleagues. When it comes to betting on yourself, however, sometimes it is good to objectively compare yourself against your peers. What are they doing that you do better? What are they doing better than you that you must get better at? Are they any things that you know that you can do better if given the right opportunity?

4. Be prepared

Be honest with yourself and understand your risks. What does a successful bet on yourself look like? What happens if you bet on yourself, and fail? How will you react if your gamble is not successful? Do you have an alternate plan

Final Thoughts

Lastly, once you’ve bet on yourself, remain focused on your goals and also practice self-compassion. Judge did not have a great start to his season in April. In fact, he had second thoughts about his bet. He even went 50 plate appearances before hitting his first home run of the season.

“But then you kick yourself in the butt and say, Nah, man,” said Judge in an interview with TIME Magazine. “Come on.”

Judge was able to turn his season around and hit 18 homers by the end of May in route to history.

Although everyone won’t be able to win big on their bets like Judge, if you are confident, know your worth, study your peers, and prepare well, then you stand a greater chance of a successful bet. And once you win big don’t forget to reward yourself!