I don’t think I would quiiiiiiite recommend criticizing people more often; I agree with your general assessment of the costs and risks. It’s more something along the lines of “own the condescension that you’re dishing”? Something like, I see a lot of people lying or curating and not wanting to admit that there are implications in what they’re doing (e.g. that they think they’re more mature than the other person).
I think that if you know in your own head that you’re taking a stance/making a claim about the other person, and proceed in open willingness to pay that cost (because you think that even with that cost, it’s the best available move) then I’m on board with what you’re doing. I think it’s often true that one is significantly/demonstrably more mature or more rational or in possession of better info, and also it’s often true that social consequence concerns limit one’s ability to be candid. I think it’s just important to notice, internally, that one holds these beliefs, because if the beliefs remain implicit and subconscious then they’re much less likely to be subjected to critical review.
I think that the claim here is slightly weaker. It is about the odds. More often than not, there won’t be much in the way of bad consequences or you can patch it up. However, occasionally people will take it really badly and you’ll destroy a friendship or relationship over it.
Yeah, I do think that I can become aware of that implicit condescension of not criticizing and update more frequently on whether someone might be worth trying to help in that way. I’m still going to avoid criticizing as a general heuristic, especially after just meeting people.