14 Professionals Who Thrive Despite Career Failures

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In a world where people barely get acknowledged for their work, it’s absurd that some folks are getting paid for failing. Sometimes, no matter how bad people are at their jobs, they still get paid to fail, come up short, and just be wrong. Who else do you think fails upward in their careers?

1. Washington Generals: The Eternal Losers

Washington Generals
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These basketball players aren’t exactly known to do well at their jobs. The last time the Washington Generals won was in 1971. 

2. College Football Coaches: Million-Dollar Fumble Coordinators

College Football
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It's scary to me that being a college football coach pays so well. You can fail at your job, lose every game, and then get paid millions in contract buyouts not to work there anymore. Take Charlie Weiss, for example. Notre Dame paid him $19 million to give up his position as coach.

3. British Prime Ministers: Brief Case Collectors

David Cameron
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British PMs get paid even if they don’t stay long. Dido Harding is often cited as an example of “repeated failure and falling upwards.” Most prime ministers are given a payout, a blank list that they can fill in with names to give peerages to, and a list of contacts for people who'll pay the £100k to do an after-dinner speech.

4. Financial Tightrope Walkers: The Sheep and Wolf of Wall Street

Wall Street
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People who exclusively trade stocks for a living run a risky business. Either they crash and burn, or they continue to fall into success no matter how bad the market is. 

5. Baseball Players: The Three-Strike Stars

Night baseball game at historic Fenway Park, Boston Red Sox, Boston, Ma., USA, May 20, 2010, Red Sox versus Minnesota Twins, attendance, 38,144, Red Sox win 6 to 2
Image Credit: Joseph Sohm / Shutterstock.com.

Professional baseball is a sport where if you’re successful 30% of the time, you are considered one of the best. You only need to hit a ball three out of ten times to be regarded as an all-time great. 

6.  CEOs: Coordinators of Bad Behavior

Elon Musk
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CEOs make top dollar, and CEOs at most Fortune 100 companies receive epic separation packages for acting up. They can destroy the company (looking at you, Elon) but still get paid millions in non-taxable shares and perks. Not to mention transitional CEOs, like Bob Chapek, who walk away with golden parachutes for making unpopular policies.

7. Managers and Admin: Meeting Masters of Nothingness

Young Multiethnic Developer Working on a Laptop Computer in Creative Office Environment. Beautiful Diverse Latin Female Project Manager is Developing Data and Scheduling a Project.
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Most management and administration are paid for doing nothing: the workers below them get the job done. In most agencies, everything would be perfectly fine if you eliminated half of the available upper administration positions. 

8. Life Coaches: Motivation Magicians

Motivation Man
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Life coaches mostly just talk and leave you feeling good and motivated. But almost none of them help you achieve something, and few, if any, are mental health professionals. Being a life coach is being paid to pep talk adults.

9. Fortune Tellers: Crystal Ball Bluffers

Tarot Reading
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In fortune telling, you’re getting paid in advance for making a prediction. All you’ve got to do is blurt out a random outcome, and when the time comes, it won’t matter if you were right or wrong since you already bagged the cash. Win-win!

10. Stock Analysts: Market Mystics

Stock Analysts
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Names such as Jim Cramer and Bear Stearns come to a member’s mind when thinking of failed successes. And then there are people like Jeff Rubin, a mainstay of the business news media, who wrote a book about how the oil price was going to $200/barrel and “took every opportunity to trumpet it.” Though the price immediately crashed, it hardly slowed him down.

11. Owner of Twitter: Unqualified Billionaires 

June 16, 2023: Elon Musk, founder, CEO, and chief engineer of SpaceX, CEO of Tesla, CTO and chairman of Twitter, Co-founder of Neuralink and OpenAI, at VIVA Technology (Vivatech)
Image Credit: Frederic Legrand – COMEO/Shutterstock.

If you’re the current owner of Twitter, you’re practically getting paid to fail at your job. Elon Musk, the CEO of Tesla, acquired Twitter not too long ago. However, even in such a short span, he successfully reduced the platform’s value from $44 billion to $20 billion.

12. Regional Vice Presidents: Passive Aggressive Pros 

Angry rude caucasian executive firing male incompetent african employee for bad work, impolite white partner telling black businessman to get out detecting fraud, prejudice and racial discrimination, bigotry, racist, racism, bigot.
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Countless companies try to eliminate business units or close regional operations if times get tough. Instead of just pulling the plug on the division and navigating the bad PR, they put someone foolish in charge. After a few years of losing money, the operation shut down, and the passive-aggressive Regional Vice President is paid for years as part of their severance package.

13. Meteorologists: Weather Witchcraft

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While it’s difficult to predict the weather, I envy that meteorologists can literally be wrong 99% of the time and still get paid for it. 

14. Corporate Commanders: Clueless Zombies 

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It’s not just the CEOs but all business executives that fail successfully. It's common for executives at big companies to get “fired” at the top level. There are no repercussions since most people can get another executive position and blame the past failure on the organization or team execution.

Most executives get paid a salary for months after not working, and they also get severance packages alongside benefits such as staying on as a consultant or having access to benefits for months.

Author: Saad Muzaffar

Title: Writer

Expertise: Gaming, Technology, Lifestyle, Books


Saad Muzaffar is an entertainment, lifestyle, and gaming writer at Wealth of Geeks. He has a Bachelor's Degree in Computer Science with a focus on Cyber Security and Data Science with an accompanying Minor in Political Science. When not writing, Saad enjoys playing the latest exclusive on his PS5 while trying to maintain his authority as the best Smash player in his group of friends. Community work is his passion, and he tries to help out whoever he can to the best of his abilities. He has one cat, Riki, and loves talking about his latest scratches. At WealthOfGeeks, Saad writes contributing lists focusing on entertainment, lifestyle, and politics.