Staring into the abyss as a core life skill

post by benkuhn · 2022-12-22T15:30:05.093Z · LW · GW · 21 comments

Contents

21 comments

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 found some important part of their life aversive to think about.


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 watching Drew make hard decisions repeatedly over the last five years. I frequently had the experience of personally flinching away from a scary thought, watching Drew confront 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 eventually switched to being drawn towards them, at least for many classes of question.

I got lucky when I found Drew, but I expect it’s possible to seek out people who are great at this. In fact, since it seems to be so important for success, I’d suggest making it one of the top things you filter for when deciding who to work with. 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. (This suggestion is speculative; I haven’t tried it.)

Another 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 strongly to romantic relationships: past a certain 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. ↩︎

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comment by AprilSR · 2023-12-21T19:10:37.159Z · LW(p) · GW(p)

While the concept that looking at the truth even when it hurts is important isn't revolutionary in the community, I think this post gave me a much more concrete model of the benefits. Sure, I knew about the abstract arguments that facing the truth is valuable, but I don't know if I'd have identified it as an essential skill for starting a company, or as being a critical component of staying in a bad relationship. (I think my model of bad relationships was that people knew leaving was a good idea, but were unable to act on that information—but in retrospect inability to even consider it totally might be what's going on some of the time.)

comment by Darmani · 2023-01-02T23:55:00.005Z · LW(p) · GW(p)

Quote for you summarizing this post:

“A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

— Tim Ferriss

Replies from: elityre
comment by Eli Tyre (elityre) · 2023-07-29T01:25:01.750Z · LW(p) · GW(p)

I think Mark Zuckerberg said this on the Tim Ferris podcast, not Ferris himself?

comment by [deleted] · 2022-12-25T12:27:00.185Z · LW(p) · GW(p)

I’d like to hear from folks with degrees in psychology what they think about the dangers of staring into the abyss and possible strategies to do it well because I'm pretty sure running through worst case scenarios is quite a common part of certain type of psychotherapy sessions on anxiety and must be rigorously researched and living in textbooks for a long time now.

Being said that, without any credentials on my side to back up that claim mind you, it does read to me like a cunningly purposeful weaponisation of pessimism and certainly strikes tone with School of Life’s multiple works (articles, videos) on pessimism I’ve been going through lately.

Replies from: guillermo-diez-bazan
comment by Guillermo Diez Bazán (guillermo-diez-bazan) · 2023-01-05T03:49:39.513Z · LW(p) · GW(p)

Last year student of psychology here. Compulsive thought about past perceived mistakes (rumination) is an extremely common disadaptive behaviour that is highly correlated with present and future anxiety disorders and depression. That is not necessarily what the OP is talking about, but I fear it might be ambiguous enough that some readers might be lead down a risky path.

The main reason it is so dangerous is because repeated thought tends to bias thinking towards previous patterns, increase the intensity of fear (that makes complex thought more difficult) and cause exhaustion that leads to less productive analysis and higher incidence of mistakes, specially in complex topics.

The recommendation is usually simple: do not ruminate. As the OP suggests, schedule a period where you can think clearly about it instead of trying to do it continuously and, if you realize you are getting overwhelmed by exhaustion and/or emotion, make sure to stop so it doesn't bias your thinking. Learning to do so is very hard for a lot of people, so they usually need to practice with outside help first.

As for the original topic, I would agree with the OP that being able to analyze a situation and take the right choice despite the common risk aversion biases is an important skill for enterpreneurs in new fields. However, it is also necessary to remember that it requires a high degree of field-specific knowledge (without it, adequate estimation of the risks is unlikely) and that the adequate amount of risk taking behaviour is field-dependent (for example, while learning a new topic being willing to risk being wrong continuously is the right choice, as it leads to faster learning, but the same is not true in finance within a highly established field. In the same vein, a person who uses a very risk adverse approach [and, as a result, is unable to take what the OP describes as difficult choices] is unlikely to prosper in the high risk high reward environment of startups).

The other factor he mentions, being able to adapt to new evidence even if it means your previous decisions were wrong is a very useful life skill, but I would focus more on "adapt to new evidence" and less on "even if it proofs you were wrong". Weighting new evidence correctly and using it to properly re-evaluate a situation is really important when making decisions, but focusing on whether one was right or wrong is a waste of precious cognitive resources. Be willing to admit you were wrong if you were, but don't conduct the analysis with a focus on proving or disproving the rightness of your previous actions, as it would bias your though either in favor (more frequently) or against (less frequently, but still happens) yourself. Focus on understanding instead. Once again, learning to do it alone is hard for a lot of people (in many senses, thought patterns are build by social interaction), so outside help is usually necessary.

Finally, being able to adequately conceptualize the current situation so a topic can be evaluated is an ability by itself. A lot of people are unable to take those "hard choices" not because they are hard, but because they are unable to apply the schemas they may have learned in business class or philosophical discussion in real life (or viceversa). That is a field of study I have not studied enough to be comfortable giving guidance on thought.

comment by Darmani · 2023-01-03T00:19:00.812Z · LW(p) · GW(p)

It does not take luck to find someone who can help you stare into the abyss. Anyone can do it. 

It's pretty simple: Get a life coach.

That is, helping people identify, face, and reason through difficult decisions is a core part of what life coaches do. And about all the questions that Ben cobbled together at the end (maybe not "best argument for" — I don't like that one) can be found in a single place: coaching training. All are commonly used by coaches in routine work.

And there are a lot more tools than the handful than the ones Ben found. These questions are examples of a handful of techniques: eliciting alternatives, countering short-term emotion and status-quo bias, checking congruence with dentity. (Many of these have catchy names like "visioning" or less-catchy names like "identity coaching," but I can't find my coach manual right now which has them listed.)

* Noticing flinching or discongruent emotions ("I heard your voice slow when you mentioned your partner, and I'm wondering if there's something behind it")

* Finding unaddressed issues ("Tell me about your last hour. What caused you stress?")

* Helping you elicit and rank your values, and then check the congruence of each choice with your values
* Helping you access your intuition ("Close your eyes and breathe. Now, one day you wake up and everything's changed / put yourself into the shoes of yourself in 10 years and tell me the first thing you see ")

* Many techniques to address negative emotions around such a decision ("If you abandon this path, what does it mean about you? Now suppose a friend did it; what would you think about them?")

* Many techniques to actually make the decision ("If you made this change, what could go wrong? Now, let's take the first thing you said. Tell me 3 ways you could get more information about how likely that is to happen?")

This also implies that, if you want to be able to do it to yourself, you can pick up a coaching book ("Co-Active Coaching" is my favorite, but I've also heard recommended "The Coaching Habit") and try it, although I think it takes a lot of practice doing it on others before you can reliably turn it inward, as it is quite difficult to simultaneously focus on the concrete problem (what the coachee does) and on evaluating and guiding the thinking and feeling (what the coach does).

There have been a number of posts like this about questions to help guide rationalists through tough decisions or emotions. I think the rationality community has a lot to learn from coaching, which in some ways is all about helping people elevate their rationality to solve problems in their own life. I gave a talk on it in 2016; maybe I should write something on it.

Context: I completed coach training in 2017. The vast majority of my work is no longer in "pure" life coaching, but the skills influence me in daily life.

comment by Ruby · 2023-01-02T04:53:53.780Z · LW(p) · GW(p)

Curated. If I've understood correctly, "staring into the abyss" is an evocative way of saying "consider the uncomfortable and/or inconvenient. And I think the ability to do this is foundational to rationality. For most people considering that you are wrong requires considering something uncomfortable. Same for considering that you have room to improve. And the willingness to consider the uncomfortable often comes from having a clear map-territory distinction. You consider the uncomfortable because if it's real, it's real even if you don't consider it.

This post provides more and better examples of considering the uncomfortable/staring into the abyss than I can point to elsewhere. Kudos! This is a good resource I expect to come back to.

comment by Zachary · 2022-12-27T21:26:45.235Z · LW(p) · GW(p)

Honestly, smoking weed has always helped me with this because it has a way of forcing those issues I'm ignoring to the surface

comment by Gordon Seidoh Worley (gworley) · 2022-12-25T01:29:11.837Z · LW(p) · GW(p)

I agree. [LW · GW] This is basically the most important life advice, as it will reliably act to generate good outcomes by forcing you to deal with the stuff that you're hung up on.

comment by Jasnah Kholin (Jasnah_Kholin) · 2023-03-05T09:58:59.834Z · LW(p) · GW(p)

Interesting! reading this post make me realize I have somehow opposite opinion. the people I respect are often the people that are good at untangling big-scary-questions, so they will not be like that. It's very much Bucket Errors [LW · GW] - If i will think on X I will have to do uncomfortable thing Y. so the mental move that helped me was to untangle.

for example, when i thought about the possibility of break up i was practically panicking. it was very irrational, disentangles from the territory emotion - the break up itself was swift and easy and I'm pretty sure i should have done in sooner except i still have no idea when. 

but the mental move that let me to think about that was to say to myself that  I DON'T HAVE TO BREAK UP. now, it's not exactly like that. i told myself we can stay together for a year. and then it was extremely clear i want to plan for this break up. and then during something like one week break up become the only possible option. 

in the same way, I didn't break up by having uncomfortable conversation. I just... didn't. it' harder to describe, but there are people that i can have emotionally vulnerable and deep conversations and people i don't. and the right move is not to have the conversations with people that it hard to have them. but to have connections with those with whom it's not hard to have those conversations. 

for this move to work it have to be honest. for example, I'm staying at my job despite the real possibility i will be able to earn more in other place because it's comfortable and moving jobs is very high cost emotionally to me. i did told myself year ago that if they don't give me the promotion they promised i leave (and i believe this is why i actually got it), but I'm still here. and I'm not sure your framing will see that as the right choice, despite the fact i did stare into the abyss and precommited to search for different job if i don't get the promotion.

there is two things here, to acknowledge something, and to change it. and you sorta conflating them here. for example, there are ultra-orthodox people here (Haredim) with some cult-like live. and there was forums (and i assume there are facebook groups) for Haredim-against-their-will. people who stare into the abyss, decided religion is a lie, and then decided it's not worth to losing all their family and friends and work place, and it's better to pretend. 

there is to see something, and there is to act on it, and it's two different things. and your framing is too much on the side of forcing yourself to do something as the only option, when I see forcing yourself to do things as form of self harm (like in Forcing yourself to keep your identity small is self-harm [LW · GW]), and prefer ways that does not include forcing yourself, and that I don't see in your map (but see in the territory).

also, I noticed now that I wrote a lot about where I disagree, and it's misleading. I VERY MUCH agreeing that do the hard thing is very important life skill. I just prefer to un-abyss the abyss before you stare at it. 
 

comment by tlevin (trevor) · 2023-01-09T01:08:22.525Z · LW(p) · GW(p)

This post has already helped me admit that I needed to accept defeat and let go of a large project in a way that I think might lead to its salvaging by others - thanks for writing.

comment by phelps-sg · 2023-08-02T04:57:28.496Z · LW(p) · GW(p)

What is the epistemic status [LW · GW] of this claim?  e.g is it based on well established evidence beyond hearsay and personal opinion? How does it relate to other well-established cognitive biases such as the sunk-costs fallacy?  Alternatively, are you conjecturing that there is a new kind of cognitive bias (that psychologists have not yet hypothesized) that causes people to persist with failing projects when it is irrational to do so?  If so, how could it be experimentally tested?

comment by Nicholas / Heather Kross (NicholasKross) · 2023-08-30T17:31:42.675Z · LW(p) · GW(p)

This came at a good time for me, here are thoughts I had:

  • Going to try "scheduled time" for this thinking, 1 evening a week. It batches abyss-thinking for all areas of my life. Unsure if this is a good way to do it or not.
  • Some of the helping-questions (plus feedback from others) have helped me immediately. For other life-areas, I'm less-certain what the "hard/icky thing I'm avoiding doing" is, since there are multiple plausible options. This might mean I'm getting un-bottlenecked on abyss-thinking and am now bottlenecked on run-of-the-mill option-generating and decision-making.
  • A few items are more "should I do what's most congruent with my personality, or force myself to do things that're less-congruent with my personality?". In hindsight it will be obvious, but it's not like this in particular is a solved problem.

Advice welcome.

comment by Pendertif (ryan-prendergast) · 2024-05-09T21:12:20.787Z · LW(p) · GW(p)

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).

I strongly disagree with this, for the reason that words are not reality. For most people, their relationships and their gods are load bearing for unarticulated reasons. arguments are going to outcompete your sacred pillars in the world of words and arguments. Challenging yourself to stare into the abyss (aka reduce your unarticulated beliefs) is more likely than not to conclude that your sacred beliefs are somehow wrong. in high dimensional space odds are that there is some suboptimal dimension.

comment by phelps-sg · 2023-08-01T16:48:50.599Z · LW(p) · GW(p)

If somebody is finding it difficult to move on from a failed project I would tend to suggest to them to "be mindful of the sunk-costs fallacy" rather then to "stare into the abyss".
https://www.lesswrong.com/tag/sunk-cost-fallacy [? · GW]

comment by David_Kristoffersson · 2023-07-15T13:37:04.645Z · LW(p) · GW(p)

Thanks for this post Ben. I think a lot of what you're saying here could alternatively be filed under "Taking ideas seriously": the dedication to follow through with the consequences of ideas, even if their conclusions are unorthodox or uncomfortable.

comment by CuriousMeta · 2023-01-02T13:02:14.274Z · LW(p) · GW(p)

Problem: Abyss-staring is aversive, for some (much) more than for others. 

In my case, awareness hasn't removed that roadblock. Psychedelics have, to some degree, but I find it hard to aim them well. MDMA, maybe?

Replies from: sharmake-farah
comment by Noosphere89 (sharmake-farah) · 2023-01-03T00:10:55.190Z · LW(p) · GW(p)

More importantly, it relies on you being able to retain your sanity, and that's not always guaranteed here.

Staring at the abyss means disabling protections from Adversarial search, and if this goes wrong it can be devastating.

Good examples of failure to retain sanity include Roko's Basilisk, as well as MIRI a few years ago.

comment by Andrew Nelson · 2022-12-26T04:48:53.722Z · LW(p) · GW(p)

Great post, absolutely agree with the value of this approach.

Wanted to add a productive question with a social angle: Who would you not want to have a serious conversation with about your life? What part of your life would you not want them poking at, and why?

My guess is that many people avoid conversations with people who they know will confront them on issues they don’t want to face. And I wonder if we can use this to our advantage by asking the question above.

If anyone tries and feels comfortable doing so, please report. I’ll try myself too.

comment by tricky_labyrinth · 2022-12-24T10:24:42.847Z · LW(p) · GW(p)

Reminds me of http://mindingourway.com/recklessness/ (and also your recent post on overconfidence).

comment by Mary Chernyshenko (mary-chernyshenko) · 2022-12-24T09:39:09.044Z · LW(p) · GW(p)

Followed the Twitter link. I actually liked it, but... is it just me, or is the word "superpowers" sensu lato (including someone suddenly dropping dead and stopping being an inconvenience) more frequent in the list than the word "money" and things like that?

I get that a lot of the questions are about interpersonal exchanges (maybe most of them). But in some ways, "money" hits harder.