I’ve always been a sucker for a grand gesture. Playing it safe has its place, but the more important something is to you, the less safe you should play it.
I think bold moves work for a lot of reasons. For one, they have a “burn the boats” quality: you’re committing to something in a way that leaves you fewer options to back out. And that’s another reason they work, because that commitment tends to be public. As long as you don’t cry wolf very often, people can see that your move is above and beyond what you normally do, and thus you effectively transmit your seriousness about what you’re trying to do. Talk is cheap, but actions speak volumes.
And maybe that’s another reason I love them. Talk is cheap, which means even when it works, it isn’t a terribly good story later. So much of what we leave behind is just the stories, so you might as well aim for at least a few great ones. Even if your bold move doesn’t work, the story of trying and failing is better than the story of how you played it safe.
Screw your courage to the sticking place, my friends.