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:

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.

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. ↩︎