Not to be overly confessional, but my worst moment as a parent in this process was when I was briefly encouraging my kid to maybe volunteer for the local organization my wife and I support the most. My intentions were not exactly check-boxey, I actually thought it would be a cool experience, but I realized (pretty quickly, fortunately), that my kid was way more comfortable volunteering time at school as a tutor and peer counselor and such.
Which of course is fine. But I also learned my lesson about providing counsel only when asked, because this is very much not my journey.