Derek Sivers Is a Control Freak

Not long into his 2010 TED talk on creativity and leadership, Derek Sivers plays a video clip of a crowd at an outdoor concert. A young man without a shirt starts dancing by himself. The audience members seated nearby look on curiously.

“A leader needs the guts to stand alone and look ridiculous,” Derek says. Soon, however, a second young man joins the first and starts dancing.

“Now comes the first follower with a crucial role… the first follower transforms the lone nut into a leader.” As the video continues, a few more dancers join the group. Then several more. Around the two-minute mark, the dancers have grown into a crowd.

“And ladies and gentlemen, that’s how a movement is made.”¹

The TED audience gives Derek a standing ovation. He bows, then does a little dance himself on stage.

No one can accuse Derek Sivers of being a conformist. During his career, he has repeatedly played the role of the first dancer. He starts with a risky move, designed to maximize his control over what he does and how he does it. By doing so, he’s at risk of looking like the “lone nut” dancing alone. Throughout Derek’s career, however, there always ended up being a second dancer who validated his decision, and then eventually a crowd arrived, defining the move as successful.

His first risky move occurred in 1992 when he quit a good job at Warner Bros. to pursue music full-time. He played guitar and toured with the Japanese musician and producer Ryuichi Sakamoto, and by all accounts was pretty good at it. His next big move was in 1997, when he started CD Baby, a company that helped independent artists sell their CDs online. In an age before iTunes, this company filled a crucial need for independent musicians, and the company grew. In 2008, he sold it to Disc Makers for $22 million.

At this point in his career, conventional wisdom dictated that Derek should move to a large house outside of San Francisco and become an angel investor. But Derek was never interested in conventional wisdom. Instead, he put all of the proceeds from the sale into a charitable trust to support music education, living off the smallest possible amount of interest allowed by law. He then sold his possessions and began traveling the world in search of an interesting place to live. When I spoke with him, he was in Singapore. “I love that the country has so little gravity, it doesn’t try to hold you here, it’s instead a base from which you can go explore,” he said. When I asked him why he’s living overseas, he replied, “I follow a rule with my life that if something is scary, do it. I’ve lived everywhere in America, and for me, a big scary thing was living outside the country.”

After taking time off to read, learn Mandarin, and travel the world, Derek has recently turned his sights on a new company: MuckWork. This service allows musicians to outsource boring tasks so they can spend more time on the creative things that matter. He started the company because he thought the idea sounded fun.

Here’s what interests me about Derek: He loves control. His whole career has been about making big moves, often in the face of resistance, to gain more control over what he does and how he does it. And not only does he love control, but he’s fantastically successful at achieving it. This is why I got him on the phone from Singapore: I wanted to find out how he achieved this feat. In more detail, I asked what criteria he uses to decide which projects to pursue and which to abandon—in essence, I wanted his map for navigating the control traps described in the last two chapters.

Fortunately for us, he had a simple but surprisingly effective answer to my question….