Top 10 Business Lessons Learned From David Letterman


I guess I’m getting to the age where many of the people and personalities that I grew up with are going to retire or fade away. Guitar legend BB King and comedian Joan Rivers have recently passed. Last fall Derek Jeter finally hung up his cleats for good. Tim Duncan and Peyton Manning will follow him into Hall of Fame retirement very soon. I just watched the Billboard Music awards kick off the show with the favorite band of my youth, Van Halen. Sadly David Lee Roth and Eddie Van Halen didn’t even resemble the Arena Rock Gods of my teenage years. I finally understand the lyrics “Where have you gone Joe DiMaggio?”

None of these endings seemed to have the same impact though as watching the last Late Show with David Letterman this past Wednesday night. I’ve literally grown up with Dave, like he’s some quirky uncle that always showed up at family events to make wisecracks about our lives.

I have to admit that as I’ve gotten a bit older, staying up till 1130pm on a weeknight happens much less than it used to. Yet like that old tee-shirt I’m unwilling to part with, I found myself reluctant to accept that someone that has made me laugh for so long will no longer be a part of the entertainment landscape.

In honor of his retirement, I’ve created a top 10 List of Business and Life lessons that I’ve learned from watching David Letterman over the past 30 years. Cheers to you Dave and thanks for the memories.

10. It’s never too late to realize that spending time with your family and friends is just as important as your career.

  1. Even in the worst possible circumstances, there can always be something to laugh about. Never underestimate the power of laughter.
  1. Be brave enough to ask people the tough questions, or the obvious ones.
  1. Stop taking yourself so seriously, nobody else does.
  1. Surround yourself with people that are much smarter and more talented than you are and watch how much better you can get.
  1. Sometimes you may have to leave a really great job in order to find the right job that fulfills your purpose.
  1. Staying true to your Core Values and your Brand isn’t always easy, neither is owning up to your mistakes, yet things always tend to work out much better in the end when you do.
  1. Know when to say when, better to leave too soon than wear out your welcome.
  1. Consistency is much more valuable in the workplace than being perfect.
  1. The true measure of a man is not what people say about you when you are here, but rather what they say about you after you are gone.

Please post your own lesson or favorite memory of David Letterman below!

Looking forward to our next conversation.

2 Comments On “Top 10 Business Lessons Learned From David Letterman”

  1. Have fun with your mom!

  2. Tim, Great top 10 list!

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