Ktixx,
It can be done, but not in a weekend. When I began longing for a DSLR, I decided to see if I could get the hobby to pay for itself. Almost a year later I have a nice little weekend business going. There are a couple of ways to go about it:
1) Get involved with a studio. I worked for a large studio shooting graduations in May and June. It was easy work; show up, push the button several hundred times, and drop the film in the bag. The studio provided the equipment and the clients. I made enough to buy my DReb, but I had to shoot a lot of grads to get there (at $100 bucks a pop).
2) Contact local wedding photographers to see if they would use you as a paid assistant. You would get a chance to shoot, but would probably not get paid much more than the studio gig.
3) Try to go on your own. This is the slowest way, and the one that requires the most commitment. This is also the way to potentially make the most money. First you need to develop a portfolio (this usually means doing a few TFP shoots), then you need to get your name out. You won't start to really make money until you build a reputation for your work and your manner.
Bottom line...it is possible, but it takes a lot of work and comittment to get there. How many weekends are you willing to give up?
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www.jamisonwexler.com
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