I think that sometimes "willingness to look stupid" can simply be a function of your power situation.
When I was a respected Principal Engineer, secure in my position, I was willing to look stupid.
When I was in a contract-to-hire position, where I had spent months looking for a job and where I was constantly judged and I thought I might be let go at any moment, I was not willing to look stupid.
When I was a long-time group leader and project architect, I was willing to look stupid.
When I worked at a place where I was in the political and religious minority, I was not willing to look stupid.
One shouldn't be afraid to look stupid in situations where that fear is groundless. But I think it's worth having some empathy for people who are in a situation where looking stupid could actually be a threat.
The author mentions this as the biggest drawback, understandably so - if getting a job depends on knowledge and confidence, which it usually does, you really need to be careful with how you come off
When I was a respected Principal Engineer, secure in my position, I was willing to look stupid.
When I was in a contract-to-hire position, where I had spent months looking for a job and where I was constantly judged and I thought I might be let go at any moment, I was not willing to look stupid.
When I was a long-time group leader and project architect, I was willing to look stupid.
When I worked at a place where I was in the political and religious minority, I was not willing to look stupid.
One shouldn't be afraid to look stupid in situations where that fear is groundless. But I think it's worth having some empathy for people who are in a situation where looking stupid could actually be a threat.