Andrew Ross Sorkin is puzzled: Why is Silicon Valley populated by one-hit wonders who have created one successful company at an early age, then withdrawn from the field as entrepreneurs to watch from the sidelines as venture capitalists? Sorkin notes that Steve Jobs was the rare exception, a serial entrepreneur.
Steve Jobs would not have been puzzled by Sorkin's observation. Jobs called Bob Dylan "one of my all-time heroes." He opened the public unveiling of the Macintosh by quoting a verse of Dylan's "The Times They Are a-Changin," and played "Like a Rolling Stone" at the public launches of both the iPhone and iPad. Jobs considered Dylan a role model:
The reference to both Picasso and Dylan suggests that Jobs had thought deeply about how to avoid losing his creativity as he grew older. Picasso was the archetypal example of a great conceptual innovator who made not a single innovation, but a series. The key to this was the independence of Picasso's innovations, for each was a new, fresh idea, unrelated to the others. Producing an important conceptual innovation requires the ability to approach familiar problems in entirely new ways. Few people can do this once, and fewer can do it more than once, for even the greatest conceptual innovators normally become wedded to their innovations. Picasso was a unique case in modern painting, who made three fundamental, revolutionary innovations within the span of less than two decades. Dylan deliberately followed Picasso in this respect, making several major innovations by abruptly changing the style and content of his music. Jobs wanted to do the same: "If you want to live your life in a creative way, as an artist, you have to not look back too much. You have to be willing to take whatever you've done and whoever you are and throw them away."
As I grew up, I learned the lyrics to all his songs and watched him never stand still. If you look at the artists, if they get really good, it always occurs to them at some point that they can do this one thing for the rest of their lives, and they can be really successful...That's the moment that an artist really decides who he or she is. If they keep risking failure, they're still artists. Dylan and Picasso were always risking failure.
For conceptual artists or entrepreneurs, the secret to becoming a serial innovator was famously given by Monty Python: make one discovery, "And Now for Something Completely Different." This is obviously more easily said than done. And why risk failure, when retiring as a one-hit wonder brings both fame and fortune? Picasso, Dylan, and Jobs all wanted more than just fame and fortune. As a young folk singer, Dylan learned from Picasso: "Picasso had fractured the art world and cracked it wide open. He was revolutionary. I wanted to be like that." And Jobs told Walter Isaacson that he'd learned from Dylan: "You always have to keep pushing to innovate. Dylan could have sung protest songs forever and probably made a lot of money, but he didn't. He had to move on ... That's what I've always tried to do"