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What Jon Stewart Can Teach Us About Career Transitions

What Jon Stewart Can Teach Us About Career Transitions

As the saying goes, "the grass is always greener on the other side." What I mean is, when many people look at successful people, all they see is the successes that got them there. Then they spiral into a pity party with themselves thinking "I'll never be as successful because I'm not as lucky as 'fill in the blank.'" Unfortunately, what many people don't see is the perserverence it takes most of these successful people to get to where they are.

For example, many look at the past 15 years of Jon Stewart’s career on The Daily Show and think that he had a meteoric rise to the top or that he had a well thought out career plan. Actually, he had many career transitions. He needed time early in life to sort out everything and decide what he wanted to do. His success is a great model to study for people who want to develop great careers.


Jon Stewart did not leave college and immediately launch his comedic career. He had a lot of career transitions along the way. Consider the jobs that he had after college as referenced in Wikipedia:

  • Contingency Planner for the New Jersey Department of Human Services
  • Contract Administrator for the City University of New York
  • Puppeteer for children with disabilities
  • Soccer Coach at Gloucester High School in Virginia
  • Caterer, busboy and shelf stocker at Woolworth's
  • Bartender at the Franklin Corner Tavern and City Gardens

Even after he made up his mind to develop a career in comedy he had a number of letdowns and setbacks. These included:

  • Losing out to Conan O’Brien to The Letterman Show
  • Being passed over as the host of The Late Late Show (went to Jimmy Kimmel)
  • Having several series cancelled due to poor ratings

This is more than a lifetime of disappointment and setback. But today we now see a successful performer at the top of his profession: winner of nineteen Emmys.

What does this tell us?

There are four lessons that you can learn from the career success of Jon Stewart.

Career paths are not straight lines

Some of us are fortunate to know what we want to do very early in life. The vast majority, though, need to learn by trial and error. This should teach us not to be afraid to try new things and new career transitions. Who knows where they will lead us.

Experience builds over time

In an earlier blog commenting on The Five Patterns of Extraordinary Careers, I wrote that professionals with successful careers seek out new experiences and challenges for the ability to grow their knowledge base and expertise. Moving to a new opportunity does not have to always be about more money or a better title. Growing your experiential learning curve is important.

Perseverance is essential

Jon Stewart is a great example of how to not let setbacks derail your hopes and ambitions. Work hard at knowing what you want and give yourself permission to pursue it.

Never stop looking for new challenges

Even at what one would think is the top of his game, Jon Stewart is leaving The Daily Show to pursue something new. This is a lesson to everyone who wants to put their career on auto pilot. Always look to push and grow yourself.