Jon stewart
Image Credit | Deadline

Jon Stewart is one the most loved and respected comedians in recent television history and is mostly responsible for the large success of The Daily Show. What most people don’t know is that he left The Daily Show to pursue his lifelong dream of directing a movie and he stumbled upon a lot of resistance when he decided to do so.

Today we outline Jon’s 3 career lessons based on his autobiography with The Daily Show: an Oral History as Told by Jon Stewart. Here’s a video version as well:  

1. People Hate Change

When John came onto The Daily Show, he was taking it over from a host who had run it for one season and during that one season it was as successful as it possibly could’ve been. The previous host got poached by one of the big three networks to become a Late Night host. That shows you how good and successful the show was.

When Jon Stewart came in to host The Daily Show it was not a news show, per se. It was more of a comedy show, similar to what was airing on Saturday Night Live. So John had to pivot this show to create one he always dreamt of watching.

Problems arose as soon as he started. One of the main issues that he came up against was everybody on the show were against Jon from the start. They had their own ideas and habits and they were trying to get Jon to host the old style Daily Show and he had to fight and actually fire most of the people that were there in order to get them to pivot to The Daily Show as it became.

Once he created his version of the show it became one of the biggest shows ever aired.

“Every generation has their challenges. And things change rapidly, and life gets better in an instant.” – Jon Stewart

2. Once You Build Something, Live Your Dream

The Daily Show made Comedy Central a household name. During the peak of the show’s popularity Jon decided to make a move that surprised everybody. Jon had this platform, he was very successful and at the height of the show Jon Stewart decided that he wanted to leave the show for a few months and direct a movie.

This movie was called Rosewater. It was about an Iranian filmmaker who gets detained and beat up in Iran. People in charge of the show and Comedy Central would not let him leave. It didn’t make sense for the show or for the network.

He had to negotiate very hard to get this and he eventually did leave the show to live his dream to become a movie director because he felt like he needed to.

So the bigger rule here is nothing lasts forever. Jon Stewart could have easily just sat at the helm of The Daily Show forever until he retired like most comedians and hosts do, but he decided that he wanted to go direct this movie and then come back.

3. Keep Going

When Jon Stewart was off directing his movie he put John Oliver, a british comedian, in charge of The Daily Show during the summer. For 2 or 3 months, those shows were extremely highly rated. They were funny. I actually saw a live taping in New York. Great reviews were just pouring in.

Jon Stewart knew at this point that he wanted to leave The Daily Show and he was preparing John Oliver to take over, when HBO came in and gave John Oliver a much bigger deal to come to their network. John agreed and The Daily Show lost its replacement host.

Jon Stewart still wanted to leave. Here lies the big lesson. Jon Stewart could have given up the search. He was leaving anyway, he could have been: ‘Okay, Comedy Central, you guys figure it out. Doesn’t really matter to me I’m retiring in a few weeks.’ Instead, he went out and he found Trevor Noah.

He found another replacement host for him. So that just goes to show you to keep going. Jon Stewart was living his other dream, he was directing, doing the stuff he loves, but he didn’t want the show to die and he didn’t let it die.

“Love what you do. Get good at it. Competence is a rare commodity in this day and age. And let the chips fall where they may.” – Jon Stewart

It’s okay to move on and it doesn’t always mean that you leave failure and destruction behind. Lots of people get stuck in a role that is perceived as successful and don’t have the courage to pursue doing something their heart tells them to.

Those are the lessons I learned from Jon Stewart’s unique career path. Why do you think most people get stuck in a role that’s not their dream one? Leave your thoughts below.


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