Apprentice Roofer. Salary: $22,350 

The best way to learn the roofing business is to work in the roofing business. You figure, hey, you like working outside, chatting with your coworkers, and have never been worried about heights. Sounds like a perfect fit.

Restless Roofer, one-two years experience. Salary: $28,000 

You're learning the ropes, experiencing a variety of jobs and working with all kinds of clients. However, you're getting kind of tired of working for somebody else. Now that you know what you're doing, you're thinking it's time to find a roof of your own.

Free as a Bird. Salary: $35,760 

Life is even better when you're the one calling the shots. You're licensed, you're bonded, and you've just responded to another home owner wanting to hire you. Things are looking up—like sky-high. For a roofer, that's the best news of all.

The Big Cheese. Salary: $47,000 

It's so much easier to climb the ladder of success when the ladder has your name on it. New homes, home repairs, and even some commercial work all have your business humming along. You've had so much business that you've had to hire some help.

Old Pro. Salary: $60,350 

Solid experience builds a solid reputation, and by now you've done everything from roofing a backyard gazebo to putting the roof on the biggest house in town. There's nowhere for you to go but up. Or you can leave that to your helpers and spend your time bidding on new projects. It's up to you. You're the boss.