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.

  • When he and his cofounder Lincoln first started a company together (well before my time), they built about 10 different social mobile apps in succession, pivoting from each one when it didn’t get traction. The decision to pivot away from a product you’ve invested a lot of effort into designing, building and distributing is painful enough that many people procrastinate on it and keep working on ideas that clearly aren’t working. In fact, Drew and Lincoln had a third cofounder who left partway through this phase in part because doing so many things that failed made him too stressed and anxious. (To be clear, this is a reasonable reaction that I probably also would have had if I’d been working with them at the time.)

  • Once they pivoted the 11th time and launched Sendwave—building money transfer from the US to Kenya by delivering to the M-Pesa mobile money system—the product grew incredibly quickly and within less than a year, a majority of the total possible users were using Wave. (I joined toward the tail end of that year.) When we tried to expand to other countries, we realized that their mobile money systems weren’t nearly as good as M-Pesa, which meant that the user experience was worse and the potential market was smaller than expected.

    The default response would have been to ignore this info and continue trying to expand Sendwave to integrate with progressively worse mobile money systems in other countries, thus implicitly accepting the constraint of smaller market size while refusing to actually acknowledge it. Instead, Drew and Lincoln realized that, if mobile money was so bad in other countries, we had the opportunity to launch a better one ourselves. In late 2015, they delegated running Sendwave to other employees, went almost completely hands-off, and moved to Africa to work on what was effectively their 12th completely different startup. It’s now really obvious that this was the right move, since Wave (the mobile money company) was recently valued at over 3x what Sendwave sold for. But that wasn’t obvious even within Wave until maybe 2019. Back in 2015 when they made the original decision to pivot, it required an absurd amount of conviction.

  • After our mobile money pilot started to take off in one country, we tried expanding to a second. Drew, I and a coworker moved there in mid-2016 and launched a pilot. But in the second country, unlike the first, one of the telecoms that we relied on for USSD ran a competing mobile money system, and we started worrying that if we got big enough, they would block us. Even though everything seemed like it was going well at the time, Drew did the research and came to the conclusion that, if that telecom decided to sabotage us, we wouldn’t be able to get the regulator to intercede, and the telecom would be able to effectively shut us down. Since the first country was still growing quickly, we decided that adding a second would be a distraction, and after a few weeks we halted the launch and went back to focusing on scaling our original country.

  • We eventually had to leave country #1 as well. After that, we tried launching in a third country, where, like the first, the telecoms didn’t compete with us. But there we had a different problem: it was possible to do instant interbank transfers, meaning that banks fulfilled much of the role of mobile money elsewhere. Our product ended up being used as a glorified ATM—users would go to our agents to withdraw cash from a linked bank account, since it was more convenient than a bank branch, but they wouldn’t use Wave to transact. We saw reasonable growth with this model, but it didn’t solve as big of a problem or have the same network effects as mobile money, and so we ultimately decided to pull out of the third country as well.

  • The next country we tried to launch in was Senegal, where we eventually found product-market fit, grew to the point where a majority of adults use Wave every month, and are now able to launch in other countries and use our network effect in Senegal to launch new products I’m really excited about.

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:

  • Eliezer Yudkowsky, one of the biggest contributors to the development of the field of AI alignment, and whose writings on rationality helped me improve my thinking a lot, wrote a great description of how he came to stare into the abyss and realize that a powerful AI wouldn’t automatically share human goals:

    When I finally saw the magnitude of my own folly, everything fell into place at once. The dam against realization cracked; and the unspoken doubts that had been accumulating behind it, crashed through all together. There wasn’t a prolonged period, or even a single moment that I remember, of wondering how I could have been so stupid. I already knew how.

    … I knew, in the same moment, what I had been carefully not-doing for the last six years. I hadn’t been updating.

    And I knew I had to finally update. To actually change what I planned to do, to change what I was doing now, to do something different instead.

    … Say, “I’m not ready.” Say, “I don’t know how to do this yet.”

    These are terribly difficult words to say…. Say, “I’m not ready to write code,” and your status drops like a depleted uranium balloon.

  • Holden Karnofsky, currently co-CEO of the Open Philanthropy Project, started out by founding GiveWell, an organization trying to find the best possible charities to donate to. He went through the following phases, each of which probably required a big shift away from a previous worldview:

    • GiveWell originally tried to find the best charities within various different cause areas (including e.g. US-focused charities). Eventually, they decided that they believed US-focused charities were sufficiently less effective overall than global health that trying to evaluate them was a distraction, and pivoted to focusing solely on charities that looked like they had the highest impact overall.

    • Originally, GiveWell focused on charities for which a robust, transparent and quantitative case could be made that they were among the highest-impact charities, which effectively required them to focus on global health where charities' effects could be studied via randomized controlled trials. Over time, he came to think the best giving opportunities might be in causes where it was hard to make a sufficiently robust and legible case to outsiders because the evidence base was weaker. This resulted in the creation of GiveWell Labs to evaluate more speculative opportunities.

      Holden described GiveWell Labs as “positioning ourselves to advise seven-figure donors”; shortly after the launch they acquired a ten-figure donor, Good Ventures, and spun out into a separate org, the Open Philanthropy Project.

    • Originally, Holden/Open Phil focused on a variety of different cause areas as a result of worldview diversification, which included global health, US policy, animal welfare, and global catastrophic risks, with Holden not focused on any one in particular. Over time, Holden updated in favor of personally being fully convinced by “longtermism”—the idea that it’s most important to focus on whatever causes are most likely to improve humanity’s long-term trajectory—eventually culminating in him promoting Alexander Berger to co-CEO to focus on the non-longtermist side so Holden could focus all his attention on longtermist grantmaking.

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.

  • For example, it’s common for students at elite colleges to follow the mantra of “do what you love” and choose a major that doesn’t have very good job prospects, without really grappling with that fact until their final year. (I’m not saying that they don’t think about it at all, just that they don’t work effectively to solve that problem, which is understandable since they mostly have way too little life experience to do so effectively and don’t get much support from their environment by default.) Many of these students ultimately end up going into finance or consulting, not because they were particularly excited about that as a career path but because it’s the easiest high-status next step from their in-retrospect-poorly-chosen major. Unfortunately, those are also career paths that require long hours and where the work is often meaningless. While I’m sure that finance and consulting are the right career choice for some elite college graduates, it seems very unlikely that it’s the best choice for nearly 50% of them.

  • Another place where people frequently fail to stare into the abyss is when they take a job that turns out not to be very good. I’ve often seen people stay in these jobs for far longer than seems reasonable, even when the job market in their field is very hot and they could easily find a better position somewhere else. Thinking about whether to leave your job is uncomfortable in a few different ways: it involves acknowledging that you made a poor decision in the past (taking your current job) that wasted a bunch of time; it involves signing up for a bunch more difficult, stressful work to interview at new jobs; and it saps your motivation to invest in getting better at your current job if you think it’s likely that you’ll leave soon. So it’s understandable that people procrastinate on staring into that abyss. But that procrastination leads to a lot of avoidable suffering.

  • Symmetrically, most managers are too reluctant to let go of employees who aren’t working out. When I’m interviewing people for managerial roles, one question I ask is to tell me about how they handled a time when one of their reports wasn’t performing well. People often say it took months between noticing the underperformance and having a tough talk with the employee about it, and describe investing unreasonable amounts of time trying to salvage the situation. Most memorably, one interviewee said they wished they had tried promoting the underperforming employee because the promotion would put them in a role more similar to their previous background, even though their company was small enough that they didn’t really need anyone in the promoted role.

  • It’s also common for people to avoid staring into the abyss about their relationship. Similarly to jobs, it’s a common observation that people stay in bad relationships for far too long, and I’d guess it’s often for similar reasons.


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:

  • If you had to leave your job today, what would you do instead?

  • What’s the best argument in favor of doing that right now?

  • If you have a partner, what’s the best argument in favor of breaking up with them?

  • Are there ways you behave that you wish you didn’t? What unacknowledged desires could be driving those?

  • What have you said “yes” to that you wouldn’t say “hell yes” to? (prompted by Alex Watt)

  • Is there something you “should” do that you’re not currently doing? Why? (prompted by Silas Strawn)

  • What bad things are you afraid of happening? Imagine in detail what it would be like if they happened. (prompted by Kamilé Lukosiute)

  • What do you need that you’re not currently getting? (—David MacIver)

  • What are you avoiding because it conflicts with some part of your identity / self-image? (—Nicholas Schiefer; more at link)

  • “What is the biggest thing in your life that you just kinda casually fell into and would you have made a conscious decision to do it if you’d known in advance everything you know now?” (—@GeniesLoki; hundreds more at link)

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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14 comments, sorted by Click to highlight new comments since: Today at 5:49 PM

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

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.

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.

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.

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.

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.

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

I agree. 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.

This is so good.  Meditation has helped me more than anything else at staring into the abyss-- you are just there with the thoughts so they are harder to ignore.  It's amazing how much you can still ignore them though!

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?

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.

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.

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

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.