This post from Dan is one of the best reads in the past few months for me. He openly talks about instances that he might look like a stupid person, and how it’s benefiting him. I highly recommend reading the full blog post .

… I frequently ask questions when there’s something I don’t understand or know, from basic stuff, “what does [some word] mean?” to more subtle stuff. On the flip side, one of the most common failure modes I see with junior engineers is when someone will be too afraid to look stupid to ask questions and then learn very slowly as a result; in some cases, this is so severe it results in them being put on a PIP and then getting fired.

… 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 thinking 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.


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