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I do some tech writing, but not for documentation. Mine usually has more of a marketing focus, usually on explaining how a given technology works, how it can be used, how it relates to other equipment and software. Have also edited fairly techie mags and run a website that covers some technical stuff in the printing industry.
One approach to get started is to find some small technology companies that need documentation written or even some copy for their web site or marketing collateral. The latter is not tech writing, but it can open doors. Nothing beats some hands-on experience. It's getting the first few assignments that's hard.
Getting some bylines also helps with credibility, especially if they are in a technical journal. Pick up some journals or magazines in the areas you are most interested in and see what the articles are like. Then figure out a topic or three and pitch the editors. You'll hear "no" a lot, but once you get something published you have more credibility as a writer. Over time, mixing tech writing (which can pay nicely) and some magazine writing (which pays poorly) is a good balance because the magazine stuff has your name on it and you begin to build a rep. And that makes getting other TW gigs easier. And with experience you can also land a FT gig as a tech writer in a company, as opposed to working freelance.
Degrees are nice but not necessary. A Bachelor's, a high degree of comfort with technology are key, and being able to write well is critical, as is being able to clearly explain technical information in simple terms. It's a bit more of an art than one might think. There are classes/courses you can take. If you are near Boston, the Harvard Extension School has a certificate course (I once considered taking it). The course I looked at was only part writing--there were classes on data structures, some programming, software and hardware test techniques, etc. You might also check out University of Phoenix, which seems to have courses on everything.
Like anything, there's no quick road to success, but writing for a living is definitely a good way to go through life.
Hope this helps. Good Luck!
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