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What Dave Chappelle can teach us all about success.

Ever since I was a child, I’ve been a major comedy fan. I started watching stand up comedy when I was 6 year old and while I didn’t understand everything Eddie Murphy and Richard Pryor were talking about I was completely enthralled in the experience of watching them on stage. I would watch their stand up specials over and over.

As an adult, comedy is a part of my life weekly. It’s pretty common to catch me at a comedy show on a Friday night in New York City or hear me playing a stand up special on Netflix in the background as I do my work. Laughter is joy and comedy is such an incredible art.

So when I heard that one of my absolute favorite comedians and creative business owner, Dave Chappelle is releasing 3 comedy specials on Netflix I almost broke my nails doing Google searches to find out the date and the backstory.

To my surprise and delight, I found out that two of the specials were ones that he’d filmed while on tour (from his vault and Netflix purchased them) and he will also record one specifically for them this year. The contract was for 60 million dollars. I was DANCING (literally) when I saw this and I’m so incredibly happy for him. What this did for him and what it is teaching the world is such a powerful example of TRUE success. 


IF you don’t know, he walked away from a $50 million dollar multi-season contract in 2005 for his VERY popular, Comedy Central show, “Chappelle Show.”  Many people called him crazy and said he was a fool or on drugs. People were disappointed; they judged him and Dave disappeared from the limelight for a few years.  

I had the same initial reaction as most people, “WTF?” However, having seen contracts that were less than favorable to artists and spent most of my life around famous people, I knew there was more to the story than meets the eye, so I applauded his decision.

To hear him speak of it now, he says that the price was “too high” for him and he felt like his audience couldn’t “SEE” him anymore and he was losing the connection and love for what he truly adored, comedy itself. The sacrifice was too great and he wasn’t willing to compromise his integrity for the money. I honor that.

As an entrepreneur you’re often faced with your spouse, parents, employers or children having no idea why you are making a certain choice because they feel differently. “What you have is so “Right” or “You’re on Top of the World or secure. Why would you give that up?”

Every level of your journey you’re going to be faced with high-stake choices that illuminate who you are and what’s in your life. Your audience and loved ones won’t know the backstory, so they are left to their own ideas and assertions.

As I thought of my own decisions in my business, I realized that they led me to an even true version of everything. I learned who my true friends were. I learned who my true supporters were. I learned of my talent, my love, my desires, my worth. I learned of the deep shame that I cared and the limiting beliefs that had plagued my existence and how to eradicate some of them. I learned of the pressure I put on myself to be what everyone wanted and how I had to live my life for me first. I learned of my personal creative power. I learned vulnerability takes an unbelievable amount of strength and courage, but it’s so freeing and beautiful.

I learned of my pure joy and awesomeness that comes from me just being who I am.

I also learned the greatest lesson of them all, I’m human and that does not strip away my divinity, my ability or identity, but adds to it.

I imagine Dave may have learned some of those same lessons.

Here’s a brief list of some of the lessons I think all creative business owners can learn from Dave Chappelle’s amazing example:

  1. Courage - We are all going to be faced with difficult situations. We are going to be faced with challenges that leave us flat on the ground. However, courage is the thing that will allow us to practice everything else in our lives successfully. Without it we can’t go on.
  2. Trust yourself above all else  - Your intuition is the wisest and best guide. While it may not make sense to anyone else or you may get a slew of other opinions (even from your own head) your inner guide will always lead you to the truth that will bring you the most peace.
  3. Honor your virtues & be true to yourself first - You have to wake up with you. You have to go to bed with you. Your character is your greatest asset so no matter what, if you honor yourself first, all else will come in the right timing and people will respect and understand that.
  4. If the price is too high it’s ok to walk away - If you’re not feeling it, whatever it is, even though it may SEEM good, even if everything is at risk, if it doesn’t feel right, you always have the choice to walk away and you should.
  5. Everything you lost will be returned to you 10-fold through pleasure - Dave may have lost 50 million dollars but what he DID was returned to what he loved, became more grounded in his sense of self and came back stronger than ever with even MORE than he bargained for AND with less work. I mean you can’t beat making 60 million for something that’s so easy for you that you did anyway because you loved it.

To me, this is true success. You have what you desire without compromising who you are. 

I’d love to know what lessons you’ve learned on your entrepreneurial journey or what you've learned that I didn't mention. Hit me up on InstagramFacebook, or Twitter and leave a comment. Let’s keep the conversation going.

And if you know someone who could benefit from this, please share it with them. Helping others is the greatest gift.

Love you Fiercely,