Flounder Mode

I said that there is an idiosyncratic magic to the way he follows his interests, which is that they’re not just an input; Kelly turns his interests into an output that he can share with others. When I asked if I was onto something, I learned that Kelly doesn’t think in outputs. For him, doing is part of learning. “I don’t really pursue a destinatio... See more

I started off by asking him whether there is a unifying theme to his seemingly diffuse life’s work, which has included old-school magazines and books, bleeding-edge technology, conservationism, photographing Asia, and teaching. “Following my interests,” he said simply.

Kelly’s Hollywood style of working has always resonated with me; it’s the way I aspire to work and largely have since starting my career. Yet now, 15 years in, I’ve become self-conscious about it. Working in Silicon Valley will convince you that starting a company with its sights on unicorn status is the only possible way to make an impact, and the... See more

Compared to this, Kelly’s version of doing his life’s work seems so joyful, so buoyant. So much less ... angsty. There’s no suffering or ego. It’s not about finding a hole in the market or a path to global domination. The yard stick isn’t based on net worth or shareholder value or number of users or employees. It’s based on an internal satisfaction... See more

I asked Kelly about the tradeoffs of focusing on a single thing if you want to be great (which is what I had been getting at before). “Greatness is overrated,” he said, and I perked up. “It’s a form of extremism, and it comes with extreme vices that I have no interest in. Steve Jobs was a jerk. Bob Dylan is a jerk.”

I started off by asking him whether there is a unifying theme to his seemingly diffuse life’s work, which has included old-school magazines and books, bleeding-edge technology, conservationism, photographing Asia, and teaching. “Following my interests,” he said simply.

It sounded awfully cutesy for someone so accomplished. I said that there is an id... See more