Fiction writers are "what-iffers." What if the hero falls into a pit of despair. What if he falls in love? What if he falls and breaks a leg? You get to a point in a story where you're a little stuck about what should happen next and the what-iffing begins. When a story is boring, it’s usually because there hasn't been enough what-iffing.
So also a life. When you get to a point where you don't know what you should do next, that's the time for some what-iffing. What if I go somewhere where no one knows me and stay anonymous for a while? What if I ask his name? What if I sell everything, grab a backpack and hit the road. Like stories, your life isn’t going to be interesting, if you don't ask "What if?”
When we’re very young, we have powerful imaginations. I remember a recurring dream in which I could fly. For a long time, I thought maybe I really could. Flying becomes winning at some sport or getting into the college you want, then maybe a particular job. I’m not saying those aren’t good, practical things to hope for, but they aren’t flying. “You get what you settle for,” as Louise said.
Meg (one of my dreams that did come true) particularly likes a bit of writing advice Tim O’Brien gave her: “Have people behave in extraordinary ways to illuminate ordinary emotions.” When you come down to it, most of what we want is pretty ordinary. How bold we are in pursuing it is what makes the difference.
There are reasons to be reticent about taking some daring leap in life—money, time, other commitments—but often as not, if our lives are boring, our biggest failure may be one of imagination.