On December 22, 1999 I appeared as a musical guest on The Late Show with David Letterman. It was one of the highlights of my career as a recording artist, and also a turning point in my life. Because in the week after appearing on his show in front of approximately 3.5 million viewers, I sold 80 CDs. And I decided to quit the music business.
There are many reasons why I sold only 80 CDs in the week after my appearance on The Late Show; the fact that I wasn’t on tour at the time is one, and my record label’s poor distribution is another. But the bottom line is that my music never connected with a larger audience, or large enough to justify continuing my life as a singer/songwriter. So I changed careers.
Fortunately, 1999 was the zenith of the dotcom boom and a friend brought me in as a freelance copywriter at the pioneer web shop, Agency.com. I didn’t have any experience with writing for the web, but nobody else seemed to either. What I learned in the music business though was how to improvise. It’s just one of the many lessons that helped get me to this career and undoubtedly shaped the kind of creative director that I am today. Lessons like, don’t tell the drummer what to play. Just hire the best drummer you can find and let him (or her) play the drums. And most important of all – if you don’t sell, you don’t eat. As the leader of my own band, I developed a very clear point of view on the purpose of marketing: to sell more of what you sell so that you can do more of what you do.
Over fifteen years have gone by since that night in 1999 when I appeared on Letterman’s show. Since that day, I’ve been presented with a lot of opportunity in this business, and I’ve managed to turn what started as a freelance gig into a career that has given me a very different type of life. It’s a satisfying life that offers daily creativity, along with many other prosaic things that I couldn’t previously imagine, like health insurance.
So it was with a range of emotions that I watched Letterman retire. I was, and am, sad to see him go. I’ll miss a nightly dose of his wit, grace and intelligence. I remain inspired by how he transformed what a talk show could be, and how he always stayed true to himself. And I feel deeply grateful to David Letterman and his staff. Yes, for allowing me to be one of the 14,082 guests who appeared on one of the 4,214 broadcasts of The Late Show. And yes, again, for his—and their—enduring support for music and musicians. But mostly for letting me walk out onto the stage of the Ed Sullivan Theater, turn to the left and see Dave, turn to the right and see Paul Shaffer, and play one of my songs. It was a great moment, and it changed my life profoundly. Just not in the way I expected it to.
Bruce Henderson is the chief creative officer-North America of Geometry Global. He tweets @BHendersonNYC