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I'm also in Chicago at the moment -- began my career as writer here back in
the late 60s. I think you raise an interesting facet of this discussion.
In my case, I started as a cub in a local newspaper...walked in off the
street and told the publisher "I want you to teach me everything you know
about journalism and publishing". I started out a proofreader and advanced
quickly into editorial, reporting, assistant editor. From there I advanced
step by step through all sorts of positions in corporations and freelancing.
I taught myself desktop publishing and grew with the Internet out of
Electronic Bulletin Boards. Meanwhile, I got a degree in Business
The break into technical writing came after a year working on the help desk
for a major computer company, learning to troubleshoot their hardware,
software and web service. Then, I went back to a software company and
essentially said the same thing...I'm at this point, I want to grow in this
direction." This was just the beginning. It began a life of excessively long
hours and continued self education which has become a way of life. (I think
most aspiring technical writers don't understand - it's a great life to
aspire to but not an end. It's just the beginning of your education and
countless long challenging hours to keep yourself up-to-speed with your
industry. Not only are you called on to learn how to simplify highly complex
concepts into plain English that can't be mis-understood but you must
constantly upgrade your technical skills and ability to use and troubleshoot
ever evolving tools of the trade.)
I have serious problems with advice being given to writers that they should
take whatever volunteer work, unpaid gigs and internships they can find. I
think this is skewing the market. There are thousands of wanna-bee writers
out there who will do anything to get their name/work into print. And, the
industry is playing on this big time. Hence, we're seeing a serious
degradation of our role. This is what's fueling the concept that any
secretary can create a website, a newsletter, a book, etc. etc.
More than that, we do beginners a disservice with this advice. Once you've
entered the market as cheap labor, you play heck trying to rise above that.
But that's a whole 'nother issue and you don't want to get me started on it.
Rather, I suggest a person develop a skill set at some level of proficiency
and start stretching it by stepping into work that challenges those limits
-- then work like the devil to exceed expectations.