David Letterman’s WOW Factor – His Legacy

On May 20, after more than 4,250 episodes, David Letterman, host of the Late Show with David Letterman, is stepping down. An iconic comedic leader whose career has spanned more than four decades, Letterman leaves behind a HUGE legacy.

As an executive, can you say the same about your career? What kind of legacy are you building? What kind of legacy will you leave behind?

While you don’t have to be a celebrity or host a TV show to leave a legacy, legacies don’t just happen. Leaving a legacy—one you actually want to be remembered for—requires intention.

Do you want to know why some executives at the end of their long careers have little in the way of a legacy to show for their efforts, while others—even if they’ve failed to reach the pinnacle of their professions—leave legacies of note? Those who leave legacies start building them early on. They focus on other people and how they can influence the ways those people think and act . . . and then they take action to make it so.

John Malone, a billionaire American business executive, philanthropist, and current chair of Liberty Media, Liberty Global, and Liberty Interactive, is a man who already has a rich legacy, even as his career is still going strong. More than 20 years ago, he declared that cable services would one day be offered a la carte. He was criticized heavily for this vision and the so-called “experts” said it would never happen.

Well, fast-forward to present day where we have cable services offered a la carte by Dish, Verizon, and many others. Malone’s vision and his subsequent influence in the marketplace are the stuff of which legacies are made.

When we become intentional about leaving a legacy, we shape our actions and our words while we’re still in the midst of our careers and we’re most able to impact others—not when we’re in our 80s and retired. Professional athletes build their legacies one touchdown, one home run, one batting title at a time from the day they start their careers to the day they retire. It’s pretty hard to swing for the fences when you’re no longer in the game. The way you go about building your legacy should be no different!

In the spirit of Letterman, here’s a Top-10 list for how to leave an intentional legacy of which you can be proud:

#10 – Be clear in your values, what makes you great. Letterman knew his brand of comedy was different from Jimmy Fallon or Jimmy Kimmel’s brand. He simply leveraged his strengths. Once you know your values, you can pass on those values to others.

#9 – Focus on making others “feel” GREAT. The esteemed Maya Angelou once said, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

#8 – Inject a little weirdness. One of Zappos’ highest values was also one of Letterman’s: in order to innovate, you have to risk being “odd” at times. You never know if the normal or crazy things you do will be embraced by your audience, but innovate anyway. You never know what will work!

#7 – Pay it forward. Your learnings come on the heels of others. Throughout your life and career, people have been generous and have taught you how to be, act, and do. Pass these learnings down to others so they may share the legacy of all of your great mentors.

#6 – Foster humility and humanity. As you get older and have more experience you might begin to believe how advanced you’ve become. Don’t believe it. We always have more to learn.

#5 – Find humor in everything. Life doesn’t have to be so serious, even in difficult times. Injecting lightness provides proper reflection and takes the stress off, even if just for a moment.

#4 – Celebrate the small victories. Work is moving so fast it’s tough to stop and acknowledge the small victories. In hindsight, it’s often these small victories that lead to great breakthroughs. Great leaders show others even the tiniest progress can mean big strides.

#3 – Grow others as a process, not as a one-time event. Being devoted to growing others takes time, dedication, intention, attention, and patience. A one-time review or the occasional “that’s great” does nothing to foster another person’s growth. The investment you make in growing others has a profound ripple effect. Stop, pause, and take the time. Never be too busy to be in the business of helping another to flourish.

#2 – Be clear about what matters to you. When you know what’s important to you, take it one step further and create a list of what is non-negotiable. Your non-negotiables become your north star of what you say “yes” or “no” to—and what you say “no” to is as equally critical as to what to say “yes” to.

#1 – Live NOW. Don’t wait to think about leaving a legacy when you are at the tail end of your career. Live the legacy you intend to leave every single day.

Letterman will be missed. His legacy, however, will have lasting impact. Design your legacy now and live it!



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