How: From generic left-liberalism towards the middle/no ideology, towards pragmatism, free-markets and neo-conservatism (think Irving Kristol, not Bush administration cretins).
Why: To me, it's mostly education, experience and life events. My foreign policy views are probably strongly shaped by Iraq and 9/11. My economic views are shaped by volunteer work with poor people in Brooklyn and a few jobs at banking institutions. My gun control views are shaped by almost being shot a couple of times. And, I think coming into my own in between the Bush reelection when I was in high school and Obama election in college was really important as well.
Jews in America always say that "He who, when young, is not a liberal has no heart; he who, when old, is not a conservative, has no head." They're all morons too, I suppose. That's okay. Evolution still happens, whether or not one chooses to accept its results.
Pretty sure that commonplace is neither Jewish, nor accurate.
Technically, the Jewish version, of course, is "He who, when young, is not a liberal has no heart; he who, when old, is not a conservative, has no money." As to its accuracy, I suppose that If you're pretty sure about something, then it must be so.
I had always heard that attributed to David Lloyd George.