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Writer's picturejon wise

Jerry Seinfeld Stubbed His Toe. Leadership Lessons from the Caffeinated Comedian.


 

Thanks for reading DESK. My name is Jon Wise. My team and I help companies grow through great marketing, comprehensive strategies, and creative problem solving. 

 

Episode Indecision

I wasn’t sure if I was going to watch another episode. The truth is, I’m not one for binge watching - the feeling that I should probably be productive and do something else normally wins out. But after a few seconds of waffling, my love for Jerry Seinfled’s gem of a show, Comedians in Cars Getting Coffee, won out. 


I love old cars - check. 

I love Jerry Seinfeld - check. 


I love watching comedians talk to each other - check check. 


[Play Episode]


As the episode went through its familiar rhythms; a mid-engine 1985 Ferrari, a ride around Manhattan commenting on the passerby’s etc, Jerry and Trevor found their way to a trendy cafe. All very normal. 


Then, some pretty sage perspective. 


Tevor to Jerry: 


I feel like you’ve already taught me so much.


Jerry to Trevor:


You don’t need to know anything. 


Everything you need to know you’ll figure it out when you need to know it.


Even if you miscalculate and make the wrong decision, you needed to know that. 


I always say that pain is knowledge rushing in to fill a gap. 


When you stub your toe on the bed, there was a gap in knowledge. 


The pain is a lot of information coming in really quickly… 


That’s what pain is.


Life is Pain - Leadership is More Pain? 


Instantly, I was thinking about the dozens and dozens of leaders I’ve met and the different levels of ‘pain’ they’ve been in trying to start, run, or grow their businesses. 


  • Finding the right business partner 

  • Finding product-market fit

  • Keeping up with changes in the marketplace

  • Over-reliance on a too-small group of customers 

  • Underestimation of something’s difficulty 

  • Overestimation of your own skills 

  • Building a product with too much technical debt 

  • How to hire great leaders or intrapreneurs

  • How to scale a sales team 

  • And on and on and on


As leaders, we feel the weight of every imperfection in our organization. We intimately know the feeling of wishing we had more information when we made past decisions. 


But this is what I love so much about business, and life for that matter, we get to keep trying. We get to take whatever we’ve learned forward with us into the next pitch, the next weekly sales meeting, the next monthly reporting session, the next quarterly review, the next startup, partnership, year, friendship, and on and on. We get to keep taking swings, hopefully getting better with each try. 


I think this is why I loved Jerry’s little truthitude so much: it gives us (me) permission to not know everything. It reframes failures, small or large, as necessary learnings on a long path of necessary learnings. This, my friends, is a very different outlook on missteps than how most of us are taught to see things. 


Maybe I’m just speaking to myself here, but when I think of the hundreds of lessons I’ve learned along the way, there’s a real sense of wishing I’d just been better, or known more, or wanting to have had more foresight. Especially earlier in my career, I had a deep unease with, what is clear to me now, was just a normal development in leadership abilities, skillset development, and experience. 


Laughing at Lunch


Just the other day I had lunch with an executive from one of our clients. We were discussing making some updates to their product messaging based on recent feedback in sales calls. We were laughing about just how difficult their product is to explain in 15 seconds (our goal for every client) because it doesn’t neatly fit into the product categories his market is used to. When we launched his product, we knew this was going to be an issue… and here it was, being an issue. Here he is, in some small form of product messaging pain. Information about what was not working, coming in to fill a gap. 


In this case, the good news is that we’ve already generated many strong leads for this client this year. So firstly, we know the product messaging is working to some extent, and secondly, we now have a wider base of friendly contacts that we can ask about the messaging. With our post-launch traction, we can continue to hone the perfect 30 word introduction for his product. This client is a very experienced leader, and his approach reminded me of Jerry’s sentiment above. 


There are things we can’t know now, and we will learn those things along the way, as we need to know them. 


Truth or Consequences


What would it look like for us to rethink failure and see it through the longer lens of learning and experience? How would that change how you lead or ask to be led? How would it change how you speak to yourself? How would it change how you speak to others? 


Drop me a note and let me know. 


j


P.S. Thanks for reading the third DESK. Did you see my last post about ketchup


P.S.S. Would you mind helping me spread the word about DESK by liking, commenting, or even sharing this post? 


 
📸Camera Roll (Call) 

A few weekends ago, I got to escape the city for Barnegat Light on LBI with friends. Snapped a few photos along the way. Click the image for a few more. 




 
🔥 Designspiration

While we're on the subject of comedians, I'm wondering if you saw KITH's work with Jimmy Fallon, Seinfeld himself, and most recently Seth Rogan? I'd like to shake the hand of the Creative Director that thought of this collaboration strategy. Each image links to their respective campaigns. 


Be sure to watch the video reveal with Jimmy Fallon. 🧑🍳



Kith x Seth Rogan

Kith x Jerry Seinfeld

Kith x Jimmy Fallon


 
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🔗 Link Lookup

JWC - Full-Service B2B Marketing for Growth-Focused Companies and Startups


Brandcamp - Everything your brand needs to thrive in 6 weeks.


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