I'm aware the OP is just an excuse to have yet another Terry thread, but I think the most important techniques for "making it" in photography are entirely unrelated to the camera.
One is knowing your element. Take >>3927057
for example. Dude works at nightclubs as a bouncer, and now takes pictures for Playboy. There's probably a bit of conceptual overlap between a nightclub's clientele, and taking pictures for Playboy. He knows his element and he works it, both behind the lens and in talking to people. Some of that comes down to dumb luck of getting in touch with the right person, but it's basic statistics to know that the more enthusiastic people you talk to (not marketers or people who use the word "networking), the better your chances are.
The other big one is confidence, which I think is a big part of Terry's success. I guarantee you the man does not second-guess himself, or ever show a shred of doubt about his decisions when shooting. If you make the client feel like you're in charge and are picking the best thing, then as long as the result is pretty, they're going to be satisfied.
tl;dr: Stop being an insecure faggot and do what you know you enjoy and are good at.