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I've been contracting for several years now. Yes, I have to do more
complicated taxes, and yes, I pay my own insurance, but the freedom from
office politics, the respect I get from being the "hired professional",
and the ability to pick and choose clients (well, most of the time
anyway), is well worth the false sense of security I had at my last
staff position.
True, I don't get paid for holidays or sick days. OTOH, I can take a
month off if I need to. I'm not limited to a corporate schedule.
My contracts sometimes state that I must be available onsite x days a
week, but the advantages of being able to work at three in the morning
if I can't sleep are hefty. I have a laptop which works well for most
jobs. It keeps the 1099/W2 line clear even when I'm onsite most of the
time.
Another advantage is that because you get paid for "overtime", you're
not asked to do jobs that can be done by someone on staff, and often you
get more recognition and can get meeting time with an SME more easily
than a staffer. You're treated differently because you are a not a fixed
asset.
Also, I *like* short contracts. I usually have 3 or 4 small contracts
juggling at a time. Many tech writers like long-term contracts (I don't
mean all of you - no flames!), but I keep occupied and have been pretty
happy with the smaller contracts. No matter how bad, they end quickly.
Plus, this way I am exposed to many different technologies in a
relatively short time.
That said, I have to also say that it takes a certain kind of
personality to thrive in an inherently unstable and often socially
exclusive environment. I'm ignored a lot of the time by people who don't
want to "waste time" getting to know someone that's not going to be
there in two months. Contractors are sometimes excluded from social
events when onsite, and when you work at home it can get a little
lonely.
Overall, I've worked for some pretty good companies. I love the 1099
life! For me, at least, the advantages far outweigh the negatives.