The compounding returns of being willing to look stupid

People frequently think I'm stupid—I notice it about once a week, and it likely happens far more often than that. This doesn't surprise me. I don't adjust my behavior to avoid seeming stupid, which of course results in people thinking I'm stupid. While there are downsides (failing interviews where the interviewer clearly thought I was stupid), the upsides have greatly outweighed the downsides over the course of my life and career.

A memorable example from college sticks with me. There was a group of students who struggled with the class material and seemed to barely understand it. One day, a friend told me that this group thought I was really dumb. The reason? I asked really stupid sounding questions.

Here's the pattern I've noticed: often, 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, complex reason that the thing is actually true. I would figure out that the obvious reason was wrong and then ask a question to understand the subtler reason. To someone who believed the obvious reason—or thought the refutation meant the thing was false—my question sounded idiotic.

The benefit of asking a stupid sounding question is small in any particular instance, but the compounding benefit over time is enormous. People who are willing to ask dumb questions and think "stupid thoughts" end up understanding things much more deeply over time. Conversely, people with very deep understanding frequently ask naive sounding questions and continue applying the techniques that got them there.

Learning from failure instead of making excuses

I first became sure of this underlying phenomenon playing competitive video games in high school. There were few enough players online back then that you'd recognize everyone and could see how much people improved over time. Most people blamed external factors—lag, luck, glitches, teammates—when they died. The most striking thing was that people who did that almost never became good. My "one weird trick" was to think about what went wrong every time something went wrong and try to improve. Most people seemed more interested in making an excuse to avoid looking stupid in the moment than actually improving, which, of course, resulted in them having many more moments where they looked stupid in the game.

This pattern extends far beyond gaming:

  • Buying the smallest box: I once went into an Apple store and asked for the computer that comes in the smallest box, which I had a good reason to want. The person helping me, despite being polite, clearly thought I was an idiot and kept explaining that "the size of the box and the size of the computer aren't the same." I knew that—I design CPUs—but saying so without establishing authority wouldn't have helped. I eventually asked them to humor me and bring out the boxes for various laptop models so I could see them, which they did, despite clearly thinking my decision-making made no sense.
  • Covid precautions: I took Covid seriously relatively early and bought a half mask respirator on 2020-01-26, using N95s I'd had on hand for the week before. The case that Covid was airborne was very strong based on existing SARS literature. Months later, people still looked at me like I was an idiot; as late as 2020-08, people would verbally make fun of me. The person I was living with found the mask too embarrassing to wear on a 1-hour round-trip BART ride and became one of the early Bay Area Covid cases, which gave her long Covid that floored her for months.
  • Air filtration: I looked into air quality and health and bought air filters for my apartment in 2012. Friends have chided me for years, and strangers sometimes tell me I'm paranoid. I added more capacity when I moved to a wildfire risk area, which increased the bluntness of people telling me I'm weird. I've been basically unimpacted by wildfire despite living through severe wildfire seasons twice, while others I know developed persistent issues—in one case, persistent asthma.
  • Work: Early in my career, working on chip verification shortly before tape-out, the head of verification wanted to re-run old tests that had virtually no chance of finding bugs instead of new generated tests that had a much better chance—both logically and empirically. He said we'd look stupid and incompetent if a bug slipped through that could've been caught by an old "golden" test. I was shocked that someone would deliberately do the wrong thing to reduce the odds of potentially looking stupid. Now I see that most people would do the wrong thing to avoid looking stupid to people who are incompetent. I think that's self-sabotaging; the gains to my career for standing up for what I believe have been so large that even ten unlucky failures wouldn't erase them.
  • Car insurance: I had to confirm three times that I only wanted coverage for damage I do to others, with no coverage for my own vehicle if I'm at fault. The agent was increasingly incredulous each time I confirmed.
  • Learning: When learning to climb, I repeatedly try the same easy move in various ways to understand what works better. Strangers have literally pointed and made snide comments. When learning to drive, I wanted to set up cones and barely hit them to understand where the edge of the car is; my father thought this was very stupid.
  • Medical care: Doctors are often very confident in their opinions and get condescending quickly if you disagree. In the most extreme case, I would have died if I'd listened to my doctor; in the next most extreme case, I would have gone blind. When getting blood drawn, I explain that I'm deceptively difficult to draw from and tell people what's worked in the past. About half the time, the nurse or phlebotomist takes my comments seriously, resulting in a painless blood draw. About half the time, they look at me like I'm an idiot and make condescending comments—and so far, everyone who's done that has failed to draw blood and/or given me a hematoma.
  • Recruiting: I have an unorthodox recruiting pitch that candidly leads with the downsides, often causing people to say I'm a terrible recruiter. I've never failed to close a full-time candidate and have brought in many people who never would've considered working for us otherwise.
  • Posting things on the internet: Self-explanatory.

High-ROI ideas require stupid thoughts

Being willing to look stupid also makes it much easier to find high-ROI ideas. If you go after trendy or reasonable sounding ideas, you have to have better ideas and execution than everyone else working on the same problem. But if you're willing to think about ideas most people consider too stupid to consider, you'll often find ideas that are both very high ROI and simple enough that anyone could've done them if they hadn't dismissed the idea out of hand.

I don't have to be nearly as smart or work nearly as hard as most people to get good results. When I have a dumb thought—one too stupid sounding for anyone else to try—I don't necessarily have to be particularly smart, talented, or hardworking to come up with valuable solutions. Often, the dumb solution is something any idiot could've come up with; the reason the problem hasn't been solved is that no one was willing to think the dumb thought until an idiot like me looked at the problem.

The downsides are mostly in judgment-heavy contexts

For things not about social judgment—winning a game, understanding something, building things—being willing to look stupid is all upside. Downside exists where social judgment matters, like interviews and dates, but even there, many apparent downsides are actually upsides. If a date thinks I'm stupid because I ask what a word means and shows it in their expression or tone, we're probably not compatible—finding that out sooner is upside.

Interviews are where I think there's the most downside. At large companies, the interviewer likely has no connection to the job or your co-workers, so their pattern of interaction has no direct bearing on the work environment. But saying things that might make people think I'm stupid is a deeply ingrained habit, and changing how I filter my thoughts just for interviews would be a large amount of work. Changing how I think so that I reflexively avoid "stupid" thoughts—which a lot of folks seem to do—would be even more costly.

Do you actually avoid looking stupid?

Ben Kuhn, on reading a draft, remarked that he realized he's actually very bad at this, at least compared to me. He asked himself why I can't just avoid saying things that make me look stupid specifically in interviews, then realized the mental processes involved must be extremely different from his. He couldn't readily think of a recent example of doing something that made someone think he was stupid.

I expect most people will read this and decide they're very willing to look stupid. This reminds me of how most people think they're creative, innovative, and take big risks. There's a difference between feeling like you're taking big risks and actually taking them—someone I know who is among the most conservative people I know cites occasionally jaywalking as a big risk they take.

I think I run into someone who thinks I'm an idiot in a way that's obvious to me around once a week—which might sound as ridiculous as saying I run into hundreds to thousands of software bugs per week. If you don't regularly have people thinking you're stupid, it's likely that at least one of the following is true:

  • You have extremely filtered interactions with people, and have filtered out anyone who'd have the reactions described here (if you count internet comments, you don't post things to the internet or don't read internet comments).
  • You are avoiding looking stupid.
  • You are not noticing when people think you're stupid.

The last one is unlikely. While sometimes people are too nice to tell me directly (I found out about the college group via a third party), just as often, the person very clearly wants me to know they think I'm stupid. It reminds me of being a pedestrian in NYC: when a driver tries to cut you off and fails, they'll often scream and gesture angrily until you acknowledge them, and if you ignore them, will try very hard to get your attention. Many people seem to think it's very important that you know they think you're stupid, and will keep increasing the intensity of their responses until you acknowledge it.

I don't go out of my way to sound stupid or 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. I'd rather spend my "weirdness points" on pushing radical ideas than on dressing unusually.

"Avoiding looking stupid" also seems to go beyond filtering comments or actions. Most people—Ben is an exception—have a real aversion to evaluating stupid thoughts. When I have an idea that sounds stupid, it's extremely difficult to get someone to really consider it. They reflexively reject it without engaging. The danger isn't having a conscious process to decide whether to broadcast stupid sounding thoughts—that seems great if low overhead—but rather having some non-conscious process automatically reject thinking about stupid sounding things altogether.

Of course, stupid-sounding thoughts are frequently wrong. 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 colleagues who can catch the stupid-sounding ideas that are actually stupid. Because almost no one attempts to hone this, it's easy to get relatively good at it by just trying.

Stories from others who operate this way

A disproportionate fraction of people whose work I really respect operate similarly with respect to looking stupid, and have stories about it. Laurence Tratt was rejected from a job at his current employer because a senior person who knew him told others he was "too stupid." He found it bemusing for a long time, then highly amusing. Gary Bernhardt once told me about chatting with someone who specialized in microservices on Kubernetes for startups; Gary said most small startups could get away with a managed platform like Heroku or Google App Engine, and the more he explained, the more sure the other person was that Gary was stupid.

There are contexts where training yourself to avoid looking stupid is more effective—where looking competent matters more than being competent. Ali Partovi has a story about how his honesty led to Paul Graham's company being acquired by Yahoo instead of his own, which eventually led to Graham founding YC. Personally, I've tried to avoid such contexts, although they're probably more lucrative than the ones I operate in.

How to not care about looking stupid

The "how" is idiosyncratic and varies greatly by person, so general advice won't be effective. For me, this came easy: I genuinely felt I was fairly stupid during my formative years, so the idea that some random person thinks I'm stupid is like water off a duck's back. I'd guess this came from two things. First, my childhood friends were all much smarter than me, and weighted by interactions, most of my interactions were with them. Second, I grew up in a fairly abusive household, where one of the minor things that went along with the abuse was regularly being yelled at, sometimes for hours, for being so shamefully, embarrassingly stupid. I wouldn't exactly recommend that path, but it seems to have worked out okay.