Important Jay-Z Letterman Lessons

Not many people know this, but when I was in my early teens, I carried a photo of David Letterman in my wallet. I was a diehard fan of his rebellious comedy. Who else rents a convertible, let's the roof and windows down, lights a cigar, and drives the car through a carwash? Without early Letterman there would be no Tom Green, Jackass, Eric Andre, or countless YouTube pranksters. I still love artists who push the boundaries.

Letterman's new Netflix special, My Next Guest Needs No Introduction, has been awesome so far. I just watched his interview with Jay-Z and it did not disappoint. I decided to write notes and share them with you here. Get ready to be inspired. 

But first, I have another thing to admit, I'm completely ignorant of Jay-Z's music. Maybe it's because at my age, I like to hear the familiar. So I listen to much of the same music I've always loved. Understand, I totally crave discovering new music, I just don't have the time. I've also never been a major hip-hop fan. This is probably from lack of exposure more than anything else. I'm no longer surrounded by friends who would share music liberally. I love plenty of "old" hip hop, but I just never got around to discovering Jay-Z's work. That said.... I've just downloaded everything and I'm digging in. Leave a comment with some newer music I should check out if you please.

Jay-Z is Picasso

At the start of Letterman's interview, he referred to Jay-Z as Picasso. Even Heather has talked about how much she admires him. Unsurprisingly, Letterman asked thought-provoking questions that led to me sharing this with you here. Here's what I learned from his interview.

Awake feeling grateful each day. Ask yourself what you're grateful for when you open your eyes. I usually wake up and my mind immediately begins to race with the daily tasks I need to accomplish. Instead, I need to slow down and focus on what I am thankful for. Our health, my family, my friendships, my home, my work, Peggy sleeping on Heather's side of the bed instead of mine.

Use your free time to create. Jay-Z did this writing rhymes on scraps of paper when he was on the street selling crack. Yes, he was a crack dealer in the projects at just sixteen years old. He would earn money to help his single mom raise four kids. My birthday will be the first day of regularly writing a daily journal. I fully commit to the idea of doing this for self-discovery and to leave Ella and Sam something special after I've left this planet mentally or physically.

Become a mentor. Mrs. Lowden, a high school teacher, took Jay-Z under her wing. I've tried to do this with community groups in Nashville, but haven't done a good enough job. I'm excited to reach back out and get this ball rolling again. Organizations like Oasis Center, Thistle Farms, Big Brothers, Conexcion Americas are all solid starting points.

Aim to create content that will last forever. I believe that by teaching improv, I'll impact participants for a lifetime. This work has me so excited. The public facing content I create may be in the shape of a podcast and certainly more writing like this post. Evergreen is key. I plan to keep this all in mind as I consider my next book.

Get to know different people. The more I know about you, the more I can relate to you. This understanding helps us become more compassionate about what others are going through. Volunteering my time will help. Attending events that draw different types of people is also important. Mix it up.

We need to understand and be aware of the invisible similarities we all have.

There is an emotional transcendence that occurs when you become a parent. This happened for me too, it's like you suddenly reach a new level of maturity. Letterman asked why this doesn't occur for other moments in our lives, Jay-Z replied it was fear stopping us.

He explained that we need to understand and be aware of the invisible similarities we all have. For example, we all crave love, integrity, and loyalty. Fear comes from the things that make us different from one another on the outside like our races, sexes, clothing, economic status symbols.

Letterman asked what Jay-Z's thoughts are about the Trump administration and where America is. Jay-Z explained that he thought Trump was a good thing for a key reason.

Trump is forcing people to have a conversation. You can't really address something that's not revealed. He is bringing out the ugly side of America we wanted to believe was gone. And it's still here. We've still got to deal with it. We have to have tough conversations. For example, why is every third black or Latino man in America in prison? Good question. I highly recommend you watch Thirteenth on Netflix for more about this urgent question.

Let's face it, we might not become the next Picasso, Jay-Z, or Letterman. But we can live rewarding lives if we follow this wisdom. That's my plan.

Be thankful, become a mentor, connect with people who are different than you, create your art and make it stand the test of time.