Willingness to look stupid

I think it is pretty hard, possibly impossible, to learn new things without appearing stupid to at least some people. It is also pretty difficult to break with a dominant trend or viewpoint without someone judging you as dumb or foolish.

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.

It is cool to see the inventory of examples provided. I haven't done an exhaustive inventory of my own examples, but things that come to mind:

• The deep exploration I've taken of the crypto ecosystem has resulted in a surprising number of people thinking that I've lost my mind and am being stupid.
• My deep distrust and cynicism of Facebook starting 10 years ago was seen by many as "tinfoil hat" weirdo behavior.
• The fact that I am both very public on the Internet, but simultaneously have a strong belief that privacy online is a critical issue. A surprising number of people (to me) think the expectation of privacy is a quant aspect of a bygone era, and I’m either a luddite or stupid to value it.

Two things that additionally come to mind.

• A constant reminder that you are not responsible, nor do you necessarily know all that influences, other peoples opinions.
• On the flip side, be cautious to not assume causality, and assume iff everyone else thinks you are wrong then you must be right. That may be true sometimes, but not always. But this essay is about judging (stupid) less than being correct.

The list of examples ends with one that I found very funny.

Posting things on the internet: self explanatory

😂