Willingness to look stupid

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Willingness to look stupid

People frequently1 think that I'm very stupid. I don't find this surprising, since I don't mind if other people think I'm stupid, which means that I don't adjust my behavior to avoid seeming stupid, which results in people thinking that I'm stupid. Although there are some downsides to people thinking that I'm stupid, e.g., failing interviews where the interviewer very clearly thought I was stupid, I think that, overall, the upsides of being willing to look stupid have greatly outweighed the downsides.

I don't know why this one example sticks in my head but, for me, the most memorable example of other people thinking that I'm stupid was from college. I've had numerous instances where more people thought I was stupid and also where people thought the depths of my stupidity was greater, but this one was really memorable for me.

Back in college, there was one group of folks that, for whatever reason, stood out to me as people who really didn't understand the class material. When they talked, they said things that didn't make any sense, they were struggling in the classes and barely passing, etc. I don't remember any direct interactions but, one day, a friend of mine who also knew them remarked to me, "did you know [that group] thinks you're really dumb?". I found that really delightful and asked why. It turned out the reason was that I asked really stupid sounding questions.

In particular, it's often the case that there's a seemingly obvious but actually incorrect reason something is true, a slightly less obvious reason the thing seems untrue, and then a subtle and complex reason that the thing is actually true2. I would regularly figure out that the seemingly obvious reason was wrong and then ask a question to try to understand the subtler reason, which sounded stupid to someone who thought the seemingly obvious reason was correct or thought that the refutation to the obvious but incorrect reason meant that the thing was untrue.

The benefit from asking a stupid sounding question is small in most particular instances, but the compounding benefit over time is quite large and I've observed that people who are willing to ask dumb questions and think "stupid thoughts" end up understanding things much more deeply over time. Conversely, when I look at people who have a very deep understanding of topics, many of them frequently ask naive sounding questions and continue to apply one of the techniques that got them a deep understanding in the first place.

I think I first became sure of something that I think of as a symptom of the underlying phenomenon via playing competitive video games when I was in high school. There were few enough people playing video games online back then that you'd basically recognize everyone who played the same game and could see how much everyone improved over time. Just like I saw when I tried out video games again a couple years ago, most people would blame external factors (lag, luck, a glitch, teammates, unfairness, etc.) when they "died" in the game. The most striking thing about that was that people who did that almost never became good and never became great. I got pretty good at the game3 and my "one weird trick" was to think about what went wrong every time something went wrong and then try to improve. But most people seemed more interested in making an excuse to avoid looking stupid (or maybe feeling stupid) in the moment than actually improving, which, of course, resulted in them having many more moments where they looked stupid in the game.

In general, I've found willingness to look stupid to be very effective. Here are some more examples:

Although most of the examples above are "real life" examples, being willing to look stupid is also highly effective at work. Besides the obvious reason that it allows you to learn faster and become more effective, it also makes it much easier to find high ROI ideas. If you go after trendy or reasonable sounding ideas, to do something really extraordinary, you have to have better ideas/execution than everyone else working on the same problem. But if you're thikning about ideas that most people consider too stupid to consider, you'll often run into ideas that are both very high ROI as well as simple and easy that anyone could've done had they not dismissed the idea out of hand. It may still technically be true that you need to have better execution than anyone else who's trying the same thing, but if no one else trying the same thing, that's easy to do!

I don't actually have to be nearly as smart or work nearly as hard as most people to get good results. If I try to solve some a problem by doing what everyone else is doing and go looking for problems where everyone else is looking, if I want to do something valuable, I'll have to do better than a lot of people, maybe even better than everybody else if the problem is really hard. If the problem is considered trendy, a lot of very smart and hardworking people will be treading the same ground and doing better than that is very difficult. But I have a dumb thought, one that's too stupid sounding for anyone else to try, I don't necessarily have to be particularly smart or talented or hardworking to come up with valuable solutions. Often, the dumb solution is something any idiot could've come up with and the reason the problem hasn't been solved is because no one was willing to think the dumb thought until an idiot like me looked at the problem.

Overall, I view the upsides of being willing to look stupid as much larger than the downsides. When it comes to things that aren't socially judged, like winning a game, understanding something, or being able to build things due to having a good understanding, it's all upside. There can be downside for things that are "about" social judgement, like interviews and dates but, even there, I think a lot of things that might seem like downsides are actually upsides.

For example, if a date thinks I'm stupid because I ask them what a word means, so much so that they show it in their facial expression and/or tone of voice, I think it's pretty unlikely that we're compatible, so I view finding that out sooner rather than later as upside and not downside.

Interviews are the case where I think there's the most downside since, at large companies, the interviewer likely has no connection to the job or your co-workers, so them having a pattern of interaction that I would view as a downside has no direct bearing on the work environment I'd have if I were offered the job and took it. There's probably some correlation but I can probably get much more signal on that elsewhere. But I think that being willing to say things that I know have a good chance of causing people to think I'm stupid is a deeply ingrained enough habit that it's not worth changing just for interviews and I can't think of another context where the cost is nearly as high as it is in interviews. In principle, I could probably change how I filter what I say only in interviews, but I think that would be a very large amount of work and not really worth the cost. An easier thing to do would be to change how I think so that I reflexively avoid thinking and saying "stupid" thoughts, which a lot of folks seem to do, but that seems even more costly.

Appendix: do you try to avoid looking stupid?

On reading a draft of this, Ben Kuhn remarked,

[this post] caused me to realize that I'm actually very bad at this, at least compared to you but perhaps also just bad in general.

I asked myself "why can't Dan just avoid saying things that make him look stupid specifically in interviews," then I started thinking about what the mental processes involved must look like in order for that to be impossible, and realized they must be extremely different from mine. Then tried to think about the last time I did something that made someone think I was stupid and realized I didn't have a readily available example)

One problem I expect this post to have is that most people will read this and decide that they're very willing to look stupid. This reminds me of how most people, when asked, think that they're creative, innovative, and take big risks. I think that feels true since people often operate at the edge of their comfort zone, but there's a difference between feeling like you're taking big risks and taking big risks, e.g., when asked, someone I know who is among the most conservative people I know thinks that they take a lot of big risks and names things like sometimes jaywalking as risk that they take.

This might sound ridiculous, as ridiculous as saying that I run into hundreds to thousands of software bugs per week, but I think I run into someone who thinks that I'm an idiot in a way that's obvious to me around once a week. The car insurance example is from a few days ago, and if I wanted to think of other recent examples, there's a long string of them.

If you don't regularly have people thinking that you're stupid, I think it's likely that at least one of the following is true

I think the last one of those is unlikely because, while I sometimes have interactions like the school one described, where the people were too nice to tell me that they think I'm stupid and I only found out via a third party, just as often, the person very clearly wants me to know that they think I'm stupid. The way it happens reminds me of being a pedestrian in NYC, where, when a car tries to cut you off when you have right of way and fails (e.g., when you're crossing a crosswalk and have the walk signal and the driver guns it to try to get in front of you to turn right), the driver will often scream at you and gesture angrily until you acknowledge them and, if you ignore them, will try very hard to get your attention. In the same way that it seems very important to some people who are angry that you know they're angry, many people seem to think it's very important that you know that they think that you're stupid and will keep increasing the intensity of their responses until you acknowledge that they think you're stupid.

One thing that might be worth noting is that I don't go out of my way to sound stupid or otherwise be non-conformist. If anything, it's the opposite. I generally try to conform in areas that aren't important to me when it's easy to conform, e.g., I dressed more casually in the office on the west coast than on the east coast since it's not important to me to convey some particular image based on how I dress and I'd rather spend my "weirdness points" on pushing radical ideas than on dressing unusually. After I changed how I dressed, one of the few people in the office who dressed really sharply in a way that would've been normal in the east coast office jokingly said to me, "so, the west coast got to you, huh?" and a few other people remarked that I looked a lot less stuffy/formal.

Another thing to note is that "avoiding looking stupid" seems to usually go beyond just filtering out comments or actions that might come off as stupid. Most people I talk to (and Ben is an exception here) have a real aversion evaluating stupid thoughts and (I'm guessing) also to having stupid thoughts. When I have an idea that sounds stupid, it's generally (and again, Ben is an exception here) extremely difficult to get someone to really consider the idea. Instead, most people reflexively reject the idea without really engaging with it at all and (I'm guessing) the same thing happens inside their heads when a potentially stupid sounding thought might occur to them. I think the danger here is not having a concious process that lets you decide to broadcast or not broadcast stupid sounding thoughts (that seems great if it's low overhead), and instead it's having some non-concious process automatically reject thinking about stupid sounding things.

Of course, stupid-sounding thoughts are frequently wrong, so, if you're not going to rely on social proof to filter out bad ideas, you'll have to hone your intuition or find trusted friends/colleagues who are able to catch your stupid-sounding ideas that are actually stupid. That's beyond the scope of this post. but I'll note that because almost no one attempts to hone their intuition for this kind of thing, it's very easy to get relatively good at it by just trying to do it at all.

Appendix: stories from other people

A disproportionate fraction of people whose work I really respect operate in a similar way to me with respect to looking stupid and also have a lot of stories about looking stupid.

One example from Laurence Tratt is from when he was job searching:

I remember being rejected from a job at my current employer because a senior person who knew me told other people that I was "too stupid". For a long time, I found this bemusing (I thought I must be missing out on some deep insights), but eventually I found it highly amusing, to the point I enjoy playing with it.

Another example: the other day, when I was talking to Gary Bernhardt, he told me a story about a time when he was chatting with someone who specialized in microservices on Kubernetes for startups and Gary said that he thought that most small (by transaction volume) startups could get away with being on a managed platform like Heroku or Google App Engine. The more Gary explained about his opinion, the more sure the person was that Gary was stupid.

Appendix: context

There are a lot of contexts that I'm not exposed to where it may be much more effective to train yourself to avoid looking stupid or incompetent, e.g., see this story by Ali Partovi about how his honesty led to Paul Graham's company being acquired by Yahoo instead of his own, which eventually led to Paul Graham founding YC and becoming one of the most well-known and influential people in the valley. If you're in a context where it's more important to look competent than to be competent then this post doesn't apply to you. Personally, I've tried to avoid such contexts, although they're probably more lucrative than the contexts I operate in.

Thanks to Ben Kuhn, Laurence Tratt, Jeshua Smith, Niels Olson, Justin Blank, Tao L., Colby Russell, Anja Boskovic, David Coletta, and Ahmad Jarara for comments/corrections/discussion.