What are you most proud of to date in your teaching career?
This may sound weird, but the thing I'm most proud of are the number of students who "friend" me on Facebook after they graduate from high school. To add to that "weirdness" is that sometimes the students who wish to stay in contact with me are not the ones I would have thought might want to do so.
The students I get friend requests from are often the students who talked back or claimed they didn't like English or didn't get the highest grades. I find this knowledge to be extremely gratifying because that means I succeeded in creating a rapport with my students, even if they didn't make the best grades.
Connecting with my students in some way that makes the ones who didn't even like my content area want to befriend me after high school, that is what I'm most proud of in my teaching career. I get to see pictures of their kids. I get to see statuses (even those non-grammatical ones which make my English teacher heart and soul cringe) about their lives. And all of that makes this teacher's heart and soul puff out with pride; I made a difference.