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I've been reading them since I was 8. When I was very young, advice columns were a window into a world I hadn't seen yet. As I got older, they remind me both that 1) a lot of people have the some problems I have, and 2) some people have problems that I would _never_ have, and 3) some of the problem I thought I'd never have, I did end up having. So you learn a lot.
Being an advice columnist is easy. Being a "famous" advice columnist is not so easy. If you just want to do it, you can throw up an advice website, get people to link to it, and start answering letters on the Internet; hundreds have. You can even try your wings by commenting on people's problems on the TFP, particularly in Tilted Living and Tilted Sexuality.
In the real world, what usually happens these days is that somebody talks a newspaper into letting them write an advice column -- and it might even be a college newspaper or a local weekly, even -- and then tries to get it syndicated, or published in several other papers as well. (I don't know the mechanics of this.) Some advice columns in local papers are written by reporters or editors on the paper who do it as just another assignment, but there's always the chance to break in.
I don't say this would be easy, and you'd actually have to prove you could do it by, well, _doing it_ for free or no many in a campus paper or small-town paper. It'd also help, in this day and age, to have a specialty: aside from general advice, you could do advice to teens, advice to college-age or 20s people, dating advice only, and so on. Oh yeah, it helps to be witty, to say things clearly and directly and with some humor.
Just having common sense, a good writing style, and some wit will get you a long way. The greats, like Ann Landers, also know a lot or have great resources to turn to when answering a letter.
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