I was driving with a friend recently and telling him about some projects that really excited me. I mentioned a new book I’m working on, an article I’m writing and this new hobby of adventure motorcycling in the desert.

He interrupted me and said, “How do you stay so motivated and so excited about things?”

It caught me off guard. I hadn’t really considered the “why” behind my list of activities. But as I thought about it, I realized that the one aspect each of these projects had to make me so motivated — the common thread — was the feeling of being in just a little over my head. In other words, doing things despite the fact that, as the marketing guru Seth Godin likes to say, “this might not work.”

Now, that may sound a little bit counterintuitive. It’s easy to wonder how doing stuff that makes you uncomfortable, and might not even work, is a source of motivation.

I’ve been thinking a lot about this paradox, and I could not get my friend’s question out of my head. I wondered whether I’m wired differently. But there’s something about a sink-or-swim environment that excites me.