I now work as a full-time professional photographer, but I spent years trying to make it freelance, and I can tell you some of the things that worked for me, as well as some of the things that my company looks for in freelancers.
This is of course the bedrock of your career as a freelancer. The first thing it needs to be is focused. No one will hire a freelancer who can’t demonstrate some work in their subject, whether it’s horses, politics, cars, food, travel or fashion. You’ll have to build a lot of that on your own, so think long and hard about the areas in which you want to specialize. Many people start building their portfolio with newspaper work; a nearby local paper will often give starting photographers credentials to cover a local event, although they may only pay $25 for a published photograph.
The physical portfolio itself has to look good. It’s your resume, so it has to grab attention right away, and demonstrate a knowledge of your subject matter. If you include a couple of 8 x 10 glossies (not from your home color printer), the rest can be on DVD.
You need to be able to provide your clients with imagery that meets their needs, so these days you must have a professional digital rig (listed at the end). If you’re going to do any product work, then you’ll need lighting equipment as well. You’ll have to be able to burn DVDs, as well as upload web content.
Go to your local library, and look at the 2006 edition of Photographer’s Market; it should give you some ideas. It won’t be easy, but once you’re established, you can end up making a very good living.
Appendix: Equipment. This is what I'd tell someone looking for a job here--we shoot classic cars...
Pro cameras—Nikon and Canon like to offer something at the top of their lineup in the $5,000 range; pros seem to feel anything less doesn’t cost enough. Entry-level pro cameras start around $1,500; this is the range in which you should start looking. Megapixels aren’t an issue here, as that refers to jpeg images, which you wont use very often. You’ll be shooting in RAW mode, so check the RAW file size, and you’ll want a good framerate or burst mode if you're doing action, at least 5 frames per seconds (fps).
“Prosumer” cameras offer some of the features of the high-end models, but with lower resolution and, more importantly, often in a less-rugged body.
Nikon vs. Canon: Nikon traditionally had about 90?f the 35mm SLR market, but Canon has made huge inroads into digital. Canon has more camera options, but there are more lenses for Nikon.
Lenses: You can operate happily with three. One close up (wide), one fast medium and one long zoom. Don’t skimp! The aperture (i.e., f/2.8) is a ratio describing how much light the lens admits; the lower that number the better, and more expensive. It’s described as lens speed, because a wide aperture enables a short (fast) exposure in lower light. This is vital for action and allows you to be free from the tripod more often. The difference in image quality between a cheap lens and good glass is breathtaking.
Your close lens can be a zoom, and will be something like a 17-55mm. Most camera kits will come with one, but it will be an f/4.0-5.6 (4.0 at 17mm focal length, 5.6 at 55mm). Don’t bother with it. Instead, find one that’s a constant f/2.8 or better for that range. These run about $1,000…If you felt confident, or poor, you could get a straight closeup lens, like a 16mm or 20mm f/2.8 or f/1.8 for under $500.
Your medium lens is your workhorse. You’ll use it for chrome shots where you have to be farther away, profile views, owner shots, specialist profiles, events. This will be something like a 28-70mm, or again if you felt poor, you could look at a straight 50, 60 or 80mm lens. I have a 50mm f/1.4, which is considered a portrait lens.
Your long lens will be the bank breaker. Good ones—like pros shoot with—run around $5,000 for a 400mm f/4 or 300mm f/2.8. But you have to have something over 200mm—this is probably where you’ll have to skimp or take what comes in a package with camera for the time being—it’ll be a 70-300 f/4.0-5.6, and it will suck. To get up to a straight 300mm f/4.0 will be about a grand.
Tripod. A pro tripod is an absolute must. Everybody here uses a Bogen/Manfrotto combination. It’ll run you about $200. You’ll determine which leg/head combination based on how much your camera/lens combination weighs.
Storage is the last item. RAW files take up a lot of room. You’ll need at least 4 gigabytes of memory in whatever card your camera takes. I have two 2gb cards, each one holds 79 photos in RAW (which equals 1,800 6mp shots).
Other stuff: A cable release or remote for the camera is must, and you’ll want a reflector (about $50). Eventually, you’ll need a sensor cleaning kit, about $100 for a year’s worth.
To get up and running, you’ll probably get some sort of ‘pro shooters kit,’ which will include the camera body, memory, 2 or three lenses and a bunch of worthless accessories. Once you’ve settled on a camera, check eBay, Abe’s of Maine, Addorama, et c. If you can afford it, but the body only and add on lenses, as it will cost less in the long run. Hypothetically, this is all tax-deductible, and of course you get to take it with you when you leave
Canon pro cameras:
Canon EOS-1DS Mark II, 16.7 Megapixel, $6,899.95
Canon EOS-1Ds, 11.1 Megapixel, $4,999.95
Canon EOS 5D, 12.8 Megapixel, $ 2,879.95
Canon EOS 30D, 8.2 Megapixel, $1,299.95
Canon EOS 20D, 8.2 Megapixel, $1,034.95
Canon EOS Digital Rebel XT 8.0 Megapixel,$674.95
Nikon pro cameras
Nikon D2Xs, 12.4 Megapixel, $4,699.95
Nikon D200, 10.2 Megapixel$1,699.95
You might be able to find a recently-discontinued Nikon D100 around, too.
Nikon D70s, 6.1 Megapixel,$679.95
My funky alternative (Nikon lenses). Check out the RAW file size—to get a larger raw file, this is the least-inexpensive alternative: http://tinyurl.com/m57ta.
Downside is a VERY SLOW burst rate. It also is unique in using AA batteries, very handy.
Fujifilm FinePix S3 Pro, 12.3 Megapixel $1,199.95