I started watching Letterman in my formative years… you know the ones where you intently watch, study and emulate people you admire. I didn’t really know what to make of it. The stunts, the disregard for celebrity, the punchlines that go nowhere. Letterman not only defined my sense of humour, but has had a great impact on my leadership.

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Top 10 Things I Learned From David Letterman

10. Self-Deprecating Humour

Letterman’s first target is always himself. During his celebrity interviews, which I only on occasion would watch due to a strong disinterest in celebrity culture, he’d make himself approachable with a joke at his own expense before he ever lobbed one out at his guests.

9. How to Smile

Broad toothy smile & then squint. Easy, right? It works wonders.

8. Make Yourself Heard With A Humbleness That Keeps You Quiet

Both in his private life and on his show, it’s how little Letterman spoke that I always found fascinating. Compared to other television entertainment, I found Letterman more of a listener, from talking to his guests to his candid and rare media interviews. I’ve translated this lesson for my own life, spending as much time as possible simply listening to a room, a community or an idea, and not being so quick to react. It’s through my reaction, understanding & empathy that I express myself.

7. Take Risks

Letterman was always known as the failed successor to Johnny Carson. When he was fired by NBC he wasn’t allowed to take their combined arsenal of late-night skits and sketches to CBS, so he had to come up with his own. What followed was magical. I still give the advice that when you’re doing something for the first time, it’s your ignorance and stubborn belief in what can work that will take you to new places (take this advice cautiously).

6. Don’t Take Yourself Too Seriously

Similar to the self-deprecating humour bit, but more important and foundational. This advice makes it much easier to handle the setbacks and unplanned directions I’ve been pulled in. I’ve learned to accept failure as a learning opportunity, rejection as a tipping point, and fear as a sign of doing something right. The important aspect of this is not to brush these setbacks aside, but incorporate them into your mission.

5. Cause A Scene

Sometimes it’s not so bad to disrupt something with a megaphone. As I was convening 200 people standing on the median of a highway under the Gardiner Expressway last weekend, I glanced around at the gawkers in their cars and it dawned on me that I wasn’t creating enough scenes. I wasn’t doing enough unexpected things. I wasn’t driving around town in a convertible filled with tacos screaming through a megaphone enough. Or taking fake orders at a drive thru.

Send in Moses!

The documentary about Improv Everywhere, We Cause Scenes, inspired further desire to interrupt someone’s day, even for a small, delightful moment. It’s worth the effort, and it’s the best way to incorporate yourself into other people’s lives. After all, “to be the arbiter of good stories is to live forever.

4. Bring Your Community Along

I have circles of friends in different communities For the most part I keep them disparate and segregated, but lessons from Letterman have taught me to bring my community along for the ride, wherever it takes me and however disinterested they might be. Build life-long friendships that stay with you. Letterman’s relationship with Rupert Gee and Mujibar & Sirajul over the years let me feel like I was a participant in a friendship, but also taught me to stay in touch, stay connected, and stay interested, regardless of how far we grow apart. Now if only I could heed this lesson.

3. Will It Float

I watched Letterman the most when I was in high school. He had moved away from the street gags that made me initially enamoured with him, and grew more into a dictatorial arbiter of pranks from behind his desk at the Ed Sullivan Theatre. Through a phone or a line to producers, he would order Spidermen into a Jamba Juice, a hose to sprayed onto an NYC street, or things to be thrown off of a roof. Some gags were good and some weren’t.

Then Letterman introduced ‘Will It Float’, and I was in love. The silliness and impracticality of this bit, alongside the over-the-top involvement of a stage performance sold me. In first year University I even tried to perform ‘Will it Float’ at dorm floor meetings using a residence garbage can and items found around our building. Consider bringing ‘Will It Float’ to your next board meeting or staff retreat.

She’s gone already Chief.

2. It Ain’t Oprah Till It’s Oprah

In similarity to staying connected to your community, Letterman’s running gags like his ‘Oprah Log’ gave me a sense of familiarity at a time in my life when everything changed. Just a few minutes each night on a familiar bit made me feel a great sense of continuity.

1. Good Taste in Music Music

Oh the music. Over the years Letterman has brought indie rockers and undervalued performers onto his show, and has been my best method of discovery for amazing artists. A big chunk of my music collection has been built on the performances on his show, and 10–15 years after a first listen on Letterman, some bands and performers remain amongst my favourite.

Thanks Dave.

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