Sam Altman's advice to "always ask" has been very helpful. I can't find the link but the sense is: do not skip asking for something you want because you assume you'll get a "no".
I audited a few classes and the difference in student behavior was immediately evident. They freely questioned assertions or topics that didn't make sense! At my first university students would just muddle on and hope to figure things out as exams approached.
That little experience changed the way I approached learning and life in a massive way.