Same here on the bold choices. My two "mistakes" (not actually regretting -- everybody has their own path) were staying at the academy too long, and secondly not asking at all, but expecting. Not smart, and actually rather neurotic.

What I've found out just in the last few years is that by making yourself valuable and then asking for what you really want will actually bring the thing to you (if it's reasonable). Preparing the question and paths forward for both outcomes is a way better strategy than losing hope and blowing up.