Staring into the abyss as a core life skill | benkuhn.netStaring into the abyss as a core life skill
December 2022<br>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<br>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.<br>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.<br>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.<br>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.<br>To try to recreate the flavor of watching Drew stare into the abyss for seven years, here are some examples.<br>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.<br>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...