You’re thinking too far ahead my friend. You know what happens when you think too far ahead? Nothing. You get paralyzed. It’s the same thing that happens when you have a big project to do, but for some reason you can’t get yourself to start. You psyche yourself out before you even take the first step... Don’t over…

Try looking at it from the opposite end of the spectrum—think about the last time a stranger started a conversation with you, were you weirded out or annoyed? Probably not. You were probably pleasantly surprised.

Right, but the idea is to be able to recognize when you are in a low stake environment. It requires that you take a step back and see the situation for what it is. And when you do that, then you realize that you have nothing to lose.

I first discovered Ryan's work a few months ago through a post on Tim Ferris's blog called "Stoicism 101: A Practical Guide for Entrepreneurs." I've been hooked on the philosophy ever since. I just finished reading Meditations. The Obstacle is the Way is next on my list.