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 believe that becoming more willing to stare into the abyss is one of the most important things you can do to become a better thinker and make better decisions about how to spend your life.


To try to recreate the flavor of watching Drew stare into the abyss for seven years, here are some examples.

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.


When I think about the other people (whom I’ve met or followed closely) whose work I most respect and who have had the biggest influence on how I think and act, they all have a similar willingness to admit that they were previously extremely wrong about things. Some other examples:

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 uncomfortable or scary, and therefore you’ll only figure them out if you’re good at staring into the abyss.

The converse of this is also true: for many people who I’ve seen struggle to improve their life, part of their problem was that they avoided thinking hard about some important part of their life because it was scary to stare at directly.


I’ve started thinking of staring into the abyss as the “one weird trick” of doing great work, because it seems to be upstream of so many other ways that people do well or poorly. So I’ve been thinking about how to become better at it.

As I mentioned, the thing that made the single biggest difference for me was spending five years watching Drew repeatedly confront hard decisions. I had the experience many times of personally flinching away from a scary thought, watching Drew address it head-on, and immediately realizing that he’d made an important decision correctly and Wave was in a much better position as a result. Eventually, whatever part of me originally flinched away from these uncomfortable questions switched to being drawn towards them, at least for many classes of question.

I got lucky to work closely with Drew, but I expect it’s possible to seek out people who are great at this. You could evaluate this while reverse-interviewing your future manager and peers: “tell me about a time you had to make a difficult decision. How did you realize it you needed to do that?” And look for evidence that they acted quickly and didn’t dither or procrastinate. If you’re looking at early-stage startups, consider making this one of the top things you look for, since it’s so important to the eventual outcome. (This suggestion is speculative; I haven’t tried 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.

Of course, it can be hard to find the right person to help you stare into the abyss. The ideal person is someone who is willing to ask you uncomfortable questions—which means you need a close enough relationship for them to feel comfortable doing that, and they need to be wise enough to figure out where the uncomfortable questions are—and they also need to be a good enough listener that talking to them about a tricky topic is fun rather than aversive. I’d expect a good therapist to be good for this, although I haven’t personally worked with one.


Staring into the abyss about your job is difficult in part because it’s easier to do good work if you’re committed to your job for a long time. 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.

This suggests that a critical part of being effective at staring into the abyss is timing. 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.

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. The abyss-staring process is sometimes formalized as well: for example, in the Quaker tradition (in which I was raised), couples who want to get married meet with a “clearness committee” to encourage them to stare into the abyss and make sure it’s the right decision for them. (I’ve never experienced a clearness committee, so I don’t know how well they achieve this goal.)


My hope with this essay is to convince you to stare into the abyss a bit more. To help with that, I’ll close with some uncomfortable but hopefully productive questions:

Thanks to everyone who suggested questions (cited above) for comments/questions/discussion.


  1. This phrase originates from a quote by Nietzche:

    He who fights with monsters should look to it that he himself does not become a monster. And if you gaze long into an abyss, the abyss also gazes into you.

    I’m probably not using “stare into the abyss” in the exact same sense Nietzche intended, since I wouldn’t really describe what I’m talking about as “fighting with a monster” or like it has the potential to turn you into a monster. However, when I described this blog post to a friend without using the term, she independently described it as “staring into the abyss,” as did Elon Musk when he said that “Being an entrepreneur is like eating glass and staring into the abyss of death” (staring into the abyss in the sense I mean is indeed a core skill of being a founder, as discussed later), so I think it’s a reasonable leap. ↩︎

Comments

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Daniel

I enjoyed this essay. It spoke to me on a level that will hopefully spark some change….

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Jesse

This was a great read

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Will

good read – appreciated this.

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Zandra

Nice post! And thank you for including so many reference links. I’ve already opened “The Magnitude of His Own Folly” and “Leave a Line of Retreat” in other tabs. :)

I’m curious - do you have any resource recommendations or thoughts about what it looks like to share this task in a relationship or community?

I’m asking because I’ve started to worry about (and sometimes resent) how often I wind up becoming an “abyss lookout” in communities. By which I mean that often, I’m the person most willing or able to identify and then make an effort to complete projects that require making many attempts, each of which is a waste of time until something sticks.

The most recent examples at home:

I find these kinds of projects extra draining too, but it seems like I’m more able to force myself to put in a lot of effort over a long period of time, and to think through no-good-choice choices. And, in each case above, I had to step in when people who took on critical roles either didn’t follow through, or did a low-effort or ultimately insufficient job.

– tldr – I need to figure out how to divide up the work for tasks that are demoralizing because doing them well requires abyss-starring.

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Leah

I doubt I’ve done this as much as I should, but I’ve definitely done it more than more friends in my social group, and I think one thing that has helped it feel possible/desirable is the kind of science fiction/fantasy I read.

There’s a lot of stories I read as a kid that are about seeing difficulty/aversion as a sign something precious might be hiding from you, and leaning into it. A few examples off the top of my head:

I was a gifted kid, and, like many of us, I had the experience of very very seldom doing things I found hard growing up. And I did hit some speedbumps (abstract algebra!) in college. But I think I benefited a lot from books that gave me a hunger for what was uncomfortable, rather than only having feedback that struggling was failing.

I think I also had a lot of “never lie” from… reading a thousand books on the Salem Witch Trials. But that one seems less portable.

I had my daughter (almost 3yo) in Montessori initially and I will again when we get off the waitlist in our new neighborhood, because the schools really emphasize struggling as a natural part of learning, and an exciting sign that you are at the edge of your mastery where you can learn new things.

Caveat: I have not always applied these mindsets well. It is actually kinda dumb to not take advil when I’m in pain because “I want to learn if I could endure this if I had to. Picking the hard thing is the noble thing!”

fabian

really appreciated your thoughts here; love the idea of fiction being able to teach you some of this.

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Gilles

Hi Ben,

Thanks again for this fantastic essay. It really resonates.

Staring into the abyss reminded me of one of the mindsets of Good-to-Great companies in Jim Collins’ book:

“Confront the Brutal Facts” “Every good-to-great company embraced what we came to call ‘The Stockdale Paradox’: you must maintain unwavering faith that you can and will prevail in the end, regardless of the difficulties, and at the same time, have the discipline to confront the most brutal facts of your current reality, whatever they might be.”

https://www.jimcollins.com/concepts/confront-the-brutal-facts.html

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Philip Dakin

Thanks Ben - really enjoyed the questions at the end.

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Damon

This was a great read Ben. This is a very interesting concept and something I’ll definitely be thinking more about going forward. Looking forward to more posts.

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bk

fucking cool

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Tomas

I was recommended this article and really enjoyed it. Definitely will read more of your work. Also thanks for the links which introduced me to another authors I did not know. Good luck to you!

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Sudheer khan

This was a great read

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Lucabrando

Loved it, thanks

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Alex

This is great. I love this framing.

The best book on that topic I’ve read so far is Guy Claxton’s ‘Hare Brain, Tortoise Mind’

Here’s how he puts it: ‘To tap into the leisurely ways of knowing, one must dare to wait. Knowing emerges from, and is a response to, not-knowing. Learning – the process of coming to know – emerges from uncertainty. Ambivalently, learning seeks to reduce uncertainty, by transmuting the strange into the familiar, but it also needs to tolerate uncertainty, as the seedbed in which ideas germinate and responses form. If either one of these two aspects of learning predominates, then the balance of the mind is disturbed. If the passive acceptance of not-knowing overwhelms the active search for meaning and control, then one may fall into fatalism and dependency. While if the need for certainty becomes intemperate, undermining the ability to tolerate confusion, then one may develop a vulnerability to demagoguery and dogma, liable to cling to opinions and beliefs that may not fit the bill, but which do assuage the anxiety.’

And also Eugene Gendlin’s body of work is mostly focused on developing better ways of ‘staring into the abyss’

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