Jon Stewart’s Lesson for Other Professionals

Last night, Jon Stewart signed off as the host of The Daily Show, his award-winning late-night talk/variety/political satire and critique show, after a run of 16 years and almost 2,600 episodes. For starters, that represents a prolific amount of creative output. (By comparison: the popular television show Cheers produced only 275 original episodes, Friends produced 236, and the original Star Trek? A mere 79.)

But the move also surprised many, regardless of whether they liked his show or not, because Stewart is leaving at what still might be considered the top of his game. Great football quarterbacks do not, as a rule, walk away when they’re still completing passes for 375 yards a game. What’s more, Stewart was not just successful. He also had impact, and he had the potential to keep having impact with that show, for some time to come.

Stewart’s agent, who is undoubtedly paid by commission, is also probably wringing his or her hands over such a star talent walking away from a safe, high-paying gig after building up such a strong reputation and track record. Most people spend a decade or two climbing to the top of their professions and then, with big sighs of relief, stay there until they retire, hoping to accrue the maximum pay and benefit from paying all those ladder-climbing dues. Doubly so in a creative field (acting, comedy, art, music, writing, etc.), where one big hit does not guarantee future success in other endeavors. And why would anyone walk away from something when the pay is big and the ability to have impact (something many working professionals crave but do not feel they have in their jobs) is still present?

Why, in other words, would anyone leave the security of a really comfortable, well-paying and even meaningful job … and leap?

Ah … but that is one of the big questions I spend a fair amount of time pondering, and writing about on this blog. I actually wrote a piece on Jon Stewart last February, and I wrote another on the courage to make career leaps, a couple of months before that. But what struck me yesterday, reading all the coverage of Stewart’s upcoming last show, was that there was also a lesson in his decision for any working professional.

One of the conundrums inherent in the ladder-climb-to-the-top scenario I painted, above, is that when you finally arrive at a point of both mastery and experience such that you can perform at a high level, and (hopefully) reap the financial rewards and accolades for that performance … it is no longer as challenging to do what you spent so long learning how to do. And if you are not challenged … if your mind is not fully engaged and if you can do that job with one hand tied behind your back … yes, the job gets much easier, but you also run the risk of becoming stale, stagnant, or bored. And maybe not today, and maybe not tomorrow, but at some point, your performance will no longer be your best. Others might not even notice that your full heart isn’t in what you’re doing anymore, or that you could do better. But you’ll know. And in many cases … you’ll end up making mistakes, or showing “B-” results.

On some level, that truth seems terribly unfair. And there are plenty of people out there who honestly do not care about staying engaged with their work, or finding new territory to explore or master, or new ways to improve and expand. Just give me the paychecks and let me hang on until I retire. I get that. And while my first reaction might be, “But I don’t want them working for me!” I have to add a strong caveat to that thought. Because in today’s increasingly stressful working environment, when engaging, well-paying jobs are scarce, and the burn-out exhaustion level of many employees is high, I understand how people who might even wish for something more are content to just get the paychecks and hang on until retirement. This is the cost from squeezing more and more out of people with fewer and fewer resources to support them.

But none of that means it’s good, for anybody. Not the company, and certainly not the individuals involved. People perform at their best if they feel engaged and passionate about what they’re doing. And you can’t just focus on productivity and efficiency and results and expect that kind of energy and passion to survive. Even if the work inherently is interesting, which not all work is. Heaping more expectations and work load on someone, unless that work entails new, engaging, and passion-inspiring elements, does not challenge them more. It just burns them out faster. Passion has to be fed, nourished, rejuvenated and cultivated. And for that to happen, people have to have opportunities to be and stay excited about what they’re doing, to grow and remain challenged and engaged … and to have some fun doing it.

This is easier, of course, at a company like Pixar, National Geographic or Google, where creativity is an inherent part of both the work and product. At a widget manufacturer or a health insurance company, the challenge is greater. But the need to find some way of engaging your, or your employees’ creative minds, and allowing them to be engaged and have fun, is still there, if you want to be at the top of your game. Because when people lose their passion, excitement, and sense of challenge, they either revert to “good enough” autopilot … or they leave.

If we are to take him at his word, part of the reason Jon Stewart is leaving The Daily Show is to spend more time with his family. News reports say they’ve just bought a farm in New Jersey. And more power to him for that. But I think another big reason he’s moving on is because he needs something new to challenge and engage him, and allow his creative talent to grow in new directions.

In some ways, I can identify with Jon Stewart. He started as a host at The Daily Show the same time as I began writing my “Flying Lessons” column at Flying magazine. And my column, like his show, ran for 16 years. Now, any piece of writing is inherently challenging to produce, whether it’s a column or a script for a television show that has to be new, funny, creative and relevant every single night. But there does come a point when producing the same basic product, with some new ingredients, becomes almost muscle memory. It no longer takes all of your creative effort to produce it. So to stay fresh, you have to push the envelope in some fashion. You have to keep growing, or you stagnate.

In my case, I began going to more adventurous locations, or flying more exotic aircraft, to keep things fresh. I also started writing for The Atlantic, founded this blog, started doing workshops and public speaking, and began working on book projects to broaden the writing and work I did. Stewart added new segments and people, and even took a leave of absence, two years ago, to direct a film. But he wants more. And I get that.

So what is the lesson for other professionals who aren’t writers or comedy show hosts? I’m not necessarily advocating quitting your job in search of something completely new and different. Sometimes that’s the right answer, but there are also reasons why many people either can’t, financially, or don’t want to, because there are good things about the job or career they have. But all of us run the risk of stagnating, even at a job we like. So the challenge for both individuals and managers is figuring out how to keep themselves, and others, somehow engaged, challenged, and excited about what they’re doing, so it doesn’t become muscle memory rote, and retirement is not the most exciting thought they have all day.

How, in other words, do you find ways to grow and have fun and be excited in what you do? How, as a manager, do you feed that passion, genuine engagement, and creativity in your employees? How do you allow or generate creative, fun options for growth and variety?

I’m not sure even Jon Stewart knows the exact answer to that one, even for himself. But the fact that he’s willing to make such a leap in the hopes of finding it underscores just how important working toward that answer is, regardless of where you work, or what you do.