Staring into the abyss as a core life skill | Ben Kuhn 

⭐⭐⭐ (I've been a huge believer since my first company that if you're going to think about large life decisions, e.g., changing jobs, plan a decision date):

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 stay and stop thinking about quitting until you’ve gotten a bunch of new information. For romantic relationships, marriage is a formalized commitment to essentially this process.

Timing matters, because you don't want to stare into the abyss too often nor too little:

If you do it too little, you’ll end up taking too long to make important life improvements; but if you do it too often, you might end up not investing enough in being great at your current job or relationship because you’re too focused on the prospect of next one.

Main point:

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.

Great examples, concluded with:

Overall, I’d say Drew “wasted” about five years of his own time on things we later pivoted away from, and over 40 employee-years total. But without the decision to declare that time wasted, we’d probably be on a much less exciting trajectory today.

Tip for getting better at it:

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 of those patterns and make progress. They can also be an accountability buddy for actually spending time thinking about the thing.