Various blogs posts (e.g. https://www.lesswrong.com/posts/Tnpp3cyEHMGthjGAf/seven-ways-to-become-unstoppably-agentic) give the advice that if you're not getting rejected enough then you're not asking for enough things.

I'm a guess culture native; if I'm rejecting you then you're well beyond where you should be and it's likely each "acceptance" before then is actually coming with a bit of grievance.

So this advice has downsides if you're doing it in a guesser heavy environment. Should we/I just be askers instead? Or what's the equivalent advice for guessers?