Staring into the abyss as a core life skill
Recently I’ve been thinking about how all my favorite people are great at a skill I’ve labeled in my head as “staring into the abyss.”1 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. Since then, I’ve become fascinated by the role that abyss-staring plays in people’s lives. I noticed that it wasn’t just Drew who is great at this, but many the people whose work I respect the most, or who have had the most impact on how I think. Conversely, I also noticed that for many of the people I know who have struggled to make good high-level life decisions, they were at least partly blocked by having an abyss that they needed to stare into, but flinched away from. So I’ve come to b
