Today I am taken by the microcosm which is the <project>McFeely</project> project team. I feel compelled to give advice even though I am no better off than they are.
I too live in that murky sysadmin/would be progammer world. I took the leap a few years ago to become a consultant (actually I was pushed). But I have one client for whom I am basically an employee - so I end up facing many of the same questions of focus, direction, goals and definition that cdent discusses in his diary. Strangely, he also brings up the calculus people - geometry people spectrum. My thesis supervisor described this as holistic thinker - linear thinker and suggested that I sat in the middle too. I compare this to my work mates who have a thirst for detail that I avoid if I can. I find myself programming less and less, but remaining very opinionated about the projects I work on. I guess that's the overview thing.
jlf (a friend of cdent) complains of being dragged into the politics of his workplace, ouch. Workplace politics is a huge problem - also do you really want to be a manager or is it the only route up in your organisation. I've often wondered what became of the chief programmer team concept pioneered by Frederick P. Brooks it's worth trying to sell the concept to management (even if only to get yourself a reputation as a creative thinker). If you haven't read Brooks' book the "Mythical Man Month" it is a classic case study of (failed?) Cathedral development methodologies.
nymia asks "how contractors like me could get into the free software and open source market". I recently won a nice contract to build a community web site (which I have to fit in after hours of my other client). It is a government contract, so although their stock contract demanded copyright ownership, they were perfectly happy to place the source under a GNU licence. There are plenty of organisations who are driven by social rather than business goals (government, unions, charities), and plenty of other businesses who wouldn't know what to do with source code if it hit them in the head. If (realistically) they will never sell their in-huse software, and it won't be of use to their direct competitors, then you should be able to sell them on Open source on the basis of price, performance, compatibility etc.
He roa rawa te kakau o taku paipa - the handle of my
pipe is way too long.
p.s. oops there is no <project> tag.