Dave Chappelle, the Stockdale Paradox, and You!

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I think it is Father’s Day in most places or a lot of places today and if you are sharing that with your family, I hope you have a nice Father’s Day. The boy wanted to get confetti and his mother, wisely, said, “I don’t know if that is a good idea.” 


I was chatting with my friend, Simon, earlier this week and he started talking with me about dealing with the pandemic. 

We were both like, “Yeah, in the moment things are cool, but the uncertainty and the monotony are killers.” 

Then, Simon told me about the Stockdale Paradox and how it was impacting him in a positive way. 

If you don’t have the chance to watch the video, it tells the story of Admiral Stockdale, the most highly decorated person to be held at the Hanoi Hilton. The story is about how he dealt with being captive and not knowing when things would end or if they would end. 

Folks assumed that Admiral Stockdale was an optimist. 

He wasn’t. 

In fact, he said that the optimists were the ones that suffered the most and were the ones that were broken by the experience. 

Why is this? 

The why is what makes the paradox important for what we are dealing with right now. 

Because to Admiral Stockdale, there were two things that were important:

First, he knew that his confinement at the Hanoi Hilton would end. He didn’t know when, but he knew it would end. 

Second, he knew that he didn’t know when it was going to end and he was going to have to deal with every bit of crap that was thrown at him every day until it ended…and that it would suck. 

That’s what most of us are dealing with now. 

We are stuck in a position where we know that the pandemic is going on and we likely don’t know a lot else…even if we are following the news and monitoring things, none of us really know what is happening. 

And, because most of us are people that like to set goals, plan, and take action…this is super frustrating. 


Because we can’t plan and set goals and take many of the actions we might normally take without some direction into when things will get back to normal and what the normal we are going to deal with is going to look like. 

Recently, I was watching Dave Chappelle receive the Mark Twain award for comedy and Sarah Silverman was honoring Dave. She talked about what made Dave special to her and she mentioned that he has maintained an ability to be surprised by what he learns.

She used the example of Dave’s first visit to Compton and how he was amazed that folks had lawns…and that didn’t connect to the image he had of Compton. Once he was talking about it, he thought the most amazing thing was that this place that folks were talking about thugs and gangs was this neighborhood with lawns and folks mowing their lawns. 

As we continue through the pandemic, two things stick out to me…

First, we need to be a lot like Dave Chappelle and be surprised by what we learn in the best way possible. Meaning, to look at the things we encounter with wonder and awe at how strange it is that something we thought X about is really like Y. 

In a lot of cases, what we are experiencing is tough for us but at the same time it can be very interesting as well…and finding it interesting or absurd doesn’t lessen anything, but it does change your perspective. 

Hopefully, in a good direction. 

Second, the Stockdale Paradox is really a great guide as we move into what seems like another phase of the pandemic. This matters because what we all have to recognize is we don’t know all that much and that many of our experts are dealing with information that changes by the second. 

Despite this, we have to be confident in knowing that this pandemic will end and the financial crisis driven by it. 

While I don’t know about optimism versus pessimism, I do know that the most productive thing any of us can do is to find a way to keep putting one foot in front of the other so that we can continue to move forward. 

If we do that, we will get through this thing and we will be able to relaunch our businesses. 

Let me know how y’all are doing! 


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