Celebrities Who Took Unusual Paths to Career Success

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“A career path is rarely a path at all. A more interesting life is usually a more crooked, winding path of missteps, luck and vigorous work. It is almost always a clumsy balance between the things you try to make happen and the things that happen to you.”

– Former Viacom President Tom Freston

Do you find yourself struggling to visualize your career path? It can be difficult to see the next steps in your career when you’re focused on the day-to-day responsibilities of your job. Not where you want to be? Relax. Many of the world’s biggest successes took some interesting turns down their own winding career paths.

Martha Stewart


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Before she became the lifestyle and homemaking powerhouse she is today, Martha Stewart was a child model, and from the age of 13 she appeared in fashion shows, print advertisements and television. After attending Barnard College, Stewart left the lights and glamour of the fashion world for the cutthroat world of Wall Street as a stockbroker with the boutique firm Monness, Williams, and Sidel.

Christopher Walken


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Christopher Walken has appeared in over 100 films that have grossed over a billion dollars. Before his inspiring film success, however, Walken worked as a lion tamer for the circus and dropped out of Hofstra University.

George Clooney


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Did you know that George Clooney was an avid baseball player growing up?  Before he became one of the most recognizable faces in film, he tried out for the Cincinnati Reds Major League Baseball franchise.  Although ultimately unsuccessful in making his professional baseball dreams come true, Clooney has since become an Academy Award-winning actor.

Ashton Kutcher


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Before being recruited by a model scout at the University of Iowa, Kutcher studied biomedical engineering. Kutcher also worked in the cereal department of General Mills to make extra money during school. Since then Kutcher has become a model, actor and entrepreneur.

Marissa Mayer


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Current President and CEO of Yahoo!, and No. 8 on Fortune Magazine’s 2013 most powerful businesswomen, Marissa Mayer’s name is recognized worldwide for her innovative and controversial leadership. After beginning her career at McKinsey & Company in a consulting job and teaching at Carnegie Mellon University, Mayer became employee No. 20 at Google and the company’s first female engineer.

A career isn’t about an end destination. Sometimes the twists and turns of your winding path may bring about more insight and learning than you could ever imagine. Take a lesson from some of the world’s most well-known names and try many things on your own road to success.