I recently wrote a blog post about something along these lines. Back in the day, freelance was the way to go. You produced the work, and then looked for someone to buy it. Nowadays, it seems like everyone wants to be hooked-up with an official gig, as if it is some kind of badge of success. Here's how I see it...
We're artists. There is something within us that yearns to create, perhaps some more than others...but it is there nonetheless. We have vision, imagination and creativity. When you receive a paycheck for doing what you love to do, you are truly living the American Dream. I think that doing creative work for payment is a mistake when handled the wrong way. You are no longer realizing your vision, it becomes the vision of whoever is holding the money. The simple truth is, less than 1% of us will hit the big time and land a photojournalism job. There's only room for so many Joe McNally's in the world, and that position is currently filled.
There are tons of freelance opportunities out there, but you have to be able to add marketing into your bag of tricks. You have to not only be able to produce good photos, but be willing to talk to people and generate a buzz about what you're doing.
Just yesterday I met a photographer at a local racetrack who was selling 4x6 prints to the drivers for $4 a pop. He had a little 6x6 canopy tent set up in the staging area, complete with laptop and photo printer. Between races, he would return to his tent, edit and print some photos, and set out on foot to find who was in them. More often than not, he was successful and people ate them up like candy. Why? Because they were great photos and this market niche was untouched by any competition.
That is where freelance photography lies today. It's not in selling pictures to TIME Magazine or the local rag. It's directly to the people.