A few years ago, while I was a young, naive college student and networking trying to get a job, I cold-emailed an alum from my school who had a very senior position at a very large investment bank. Incredibly nice guy, had me in his office for a pretty lengthy chat, and while we exchanged a couple more friendly emails we haven't been in touch for a few years. Fast-forward three years and I'm working in banking and hate it. I like finance but want to explore something different than my current position. I'd like to reach out to this guy but don't want to come off as too forward (which a college kid can get away with). At the same time, I don't want to seem too clueless ("I was wondering if you could talk about some opportunities that might be available outside my narrow part of the business") because I know what those other avenues are and anyone with a couple years experience in banking should too. So how can I approach this guy without seeming like the needy d-bag I am?