Another abyss-staring strategy I’ve found useful is to talk to someone else. One reason that I sometimes procrastinate on staring into the abyss is that, when I try to think about the uncomfortable topic, I don’t do it in a productive way: instead, I’ll ruminate or think myself in circles. If I’m talking to someone else, they can help me break out... See more

The same principle applies even more to romantic relationships: past some threshold of compatibility, much of your relationship’s value comes precisely from the fact that the two of you expect to being together for a long time, and can make correspondingly long-term investments in making your relationship awesome.

One solution to the timing problem is to check in about your abyss-staring on a schedule. For example, if you think it might be time for you to change jobs, rather than idly ruminating about it for weeks, block out a day or two to really seriously weigh the pros and cons and get advice, with the goal at the end of deciding either to leave, or to... See more

It’s interesting to me that these people have both become very personally accomplished, and have produced ideas or writing that have had a big influence on how I think. This makes sense since both making effective life decisions and having novel insights require you to figure out non-obvious true things about the world, which are sometimes... See more