Staring into the abyss means thinking reasonably about things that are uncomfortable to contemplate, like arguments against your religious beliefs, or in favor of breaking up with your partner. It’s common to procrastinate on thinking hard about these things because it might require you to acknowledge that you were very wrong about something in the past, and perhaps wasted a bunch of time based on that (e.g. dating the wrong person or praying to the wrong god). However, in most cases you have to either admit this eventually or, if you never admit it, lock yourself into a sub-optimal future life trajectory, so it’s best to be impatient and stare directly into the uncomfortable topic until you’ve figured out what to do.

The first time I learned what really exceptional abyss-staring looks like, it was by watching Drew, the CEO of Wave. Starting a company requires a lot of staring into the abyss, because it involves making lots of serious mistakes (building the wrong thing, hiring the wrong person, etc.); to move quickly, you need to be fast at acknowledging and fixing them. Drew was extremely willing to tackle uncomfortable decisions head-on—“should we not have hired this person?” “Should we pivot away from this business that is pretty good but not great?”—and every time, it was immediately obvious that the decision he made was a big improvement.