The big win is when you refuse to settle for average or mediocre.

I wonder why anyone would hesitate to be generous with their writing. I mean, if you really want to make a living, go to Wall Street and trade oil futures ... We're writers. We're doing something that is inherently a generous act. We're exposing ourselves to the muse and to the things that frighten us. Why do that if you're not willing to be generous? And paradoxically, almost ironically, it turns out that the more generous you are, the more money you make. But that's secondary. For me, the privilege of being generous is why I get to do this.

Two elements of successful leadership: a willingness to be wrong and an eagerness to admit it.

My new favorite word is 'awkward.'...Th e reason we need to be in search of awkward is that awkward is the barrier between us and excellence, between where we are and the remarkable. If it were easy, everyone would have done it already, and it wouldn't be worth the effort.

The market and the consumer and idea trump the system.

When you walk around braced for impact, you're dramatically decreasing your chances. Your chances to avoid the outcome you fear, your chances to make a difference, and your chances to breathe and connect.

The wettest, weirdest environment is human interaction. Whatever we build gets misunderstood, corroded and chronic, and it happens quickly and in unpredictable ways. That's one reason why the web is so fascinating-it's a collision between the analytic world of code and wet world of people.