Dave Chappelle

Career lessons from Dave Chappelle

Melissa Allen|

Everyone loves hearing epic job quitting stories. But arguably the most epic was in 2005 with Dave Chappelle’s walking off of the set while they were filming the third season of his television show, Chappelle’s Show, and never looking back. At the time it appeared as if we has at the pinnacle of career and the height of his popularity having spent decades honing his gift of comedy. But he’d had enough, and left, walking away from a $50 million dollar contract, massive career trajectory, and adoring fans.

Last night, Chappelle appeared on the Late Night with David Letterman, presumably there to promote his new act. While the initial banter was light, witty, and friendly, Letterman steered the conversation towards what we all kind of wanted to know. During this interview, it became evident that there were a few things we could all learn from Dave Chappelle-gate.

Own up to your mistakes

“Sometimes I listen to a Jay-Z record and it starts making me feel bad about some of the choices I made. This guy’s had more fun in two songs than I’ve had in 11 years,” Chappelle told Letterman. Ouch. So maybe he should have found a more diplomatic way of voicing his frustrations, instead of leaving an entire television network hanging. He may have been able to compromise, or even convince the network of his point of view, saving his contract and earning tens of millions of dollars in the process. We all have made choices that we regret but if we own up to our mistakes, then we can learn from them, and hopefully never repeat them again.

Have an escape plan

We’re all fascinated with Dave Chappelle’s story partly because he did what many of us fantasized about doing: sticking it to The Man. Only he was able to do it, because he could afford it. For a soft landing, you need a safety net.

Maintain your integrity.

You’ll be coerced, guilt-tripped and tempted to doing things that don’t align with your beliefs. Be firm but gentle about not giving in. A few years ago, one of my friends told me about how his former boss wanted him to sign off on a client document with a couple of “fudged” numbers. He refused to do it, and when the work atmosphere got tense, he found another job. A year later, the firm was forced to close when it started losing all of its clients. If Chappelle walked away from his television deal because conflicting values, then by refusing to back down, he maintained his integrity. While it looks like he “lost out” on $50 million dollars, the long term damage could have cost a lot more. Your integrity is an investment in your future.

Money isn’t everything

On the topic of integrity, it’s really hard to put a price on it, but it sure is easy (and fun) to buy lots of cool stuff with the money you made sacrificing this vague notion of “personal integrity.” As Chappelle joked in the Letterman interview, “Let me take some integrity home and make the kids some integrity sandwiches.” He admits that while money can make him happy, so can a lot of other things. So figure out what really matters, and nurture that, because as he also said, “money is the fuel for choices…but it’s not the end all be all.”

A comeback is possible

Chappelle has been touring for a couple years now and now has a practically sold out series of shows at Radio City Hall in New York City. By steadily continuing to do great work it is possible to rebuild a rewarding career.

Because great work is timeless

Dave Chappelle is a genius. I laughed all through the Letterman interview, even in its darkest, most existential moments. People still quote his stand up and his T.V. show to this day. Sure, for the past few years, his name is often associated with his sudden disappearance almost a decade ago, but there’s proof enough that his actual work will be remembered for generations to come.

Dave Chappelle’s story is complex and enduring. The public has not lost their fascination with his narrative because it touches a nerve within all of us. Whether under extreme stress, the victim of bullying and harassment, or forced to perform work that goes against your values, could you just get up and walk away? Most of us can’t, but he could. And he did. Only time will tell if he regains his past glory, or if he even really wants it, but even for those of us who do not have his resources or clout, we must remember that we are always in charge of our personal brand, and it’s up to us to shape our own story.


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