Here’s my best secret for pitching investors, picking up women, and speaking in front of crowds:

Look comfortable.

That’s it. Most people would say the secret is to look confident. But, really, what does confident look like? How do you fake confident?

Comfortable, on the other hand, is much clearer. And, it turns out, comfortable is much more powerful, a much better synonym for the elusive ‘cool’.

I’ve noted as much of late in the world of politics. Take, for example, the Alfred E. Smith benefit dinner a few weeks back, where McCain and Obama both presented self-deprecating standup. McCain killed, as he appeared completely serene while making fun of himself. Obama, on the other hand, read his jokes stiffly and with clear reservation, and more or less bombed by comparison.

Then, on the other hand, take the Presidential debates. Here, the balance shifted in the other direction. While McCain seemed stiff, angry and stressed, Obama seemed relaxed, in his element. Obama looked comfortable.

Or consider Saturday Night Live. On each of his passes through the show, McCain was clearly willing to play along. His running mate, however, wasn’t. Despite the hype leading to her appearance on Saturday Night Live, Palin ended up mainly serving as a prop, a wax statue of herself. She was so clearly uncomfortable that she became, arguably, the first politician in the history of SNL to seem less cool after her appearance.

Which, then, also yields the corollary to my “cool = comfortable” theorem, which I’ll henceforth refer to as Palin’s Law:

People uncomfortable with playing dumb in a comedy sketch are usually complete and total idiots in real life.