Which I.T. path should I take?

This is a problem I wrestle with all the time. (As well as most people in the IT field)

Specializing is a high risk/reward. For example, getting all the way to the CCIE, for example, makes you a specialist with a huge earning potential. CCIEs are near the top on salary surveys, but it does limit you to one field. (OK, if you get multiple CCIEs, you can go down different paths, but still.) There is a narrow list of employers who can and will hire CCIEs. Being more generalized gives you a better chance of getting employed, but it can limit your advancement down the road. One thing I have noticed is that as companies have cut back on staffing, they are looking for more jack of all trade types. Like I said, though, this could come back to haunt you as you try to move up through the non-management ranks. From what I have seen, though, most IT pros tend to start out as generalists, then either through necessity or enjoyment, end up specializing in something.

I have ended up being more of a generalist, due to necessity. Someone leaves or gets reassigned, and the company needs a backup in an area, and I get volunteered. At a previous job, I became a SAN administrator after the primary guy left, and the backup got promoted. I became the new backup, even though I had never done it before. When I got to my current job, I quickly found out I was about #4 on the Cisco depth chart, but that nobody wanted to be the server jockey, so I moved more into that role. It's not all bad, though, as it's also how I stumbled into the world of Macs.

 

I am pretty much in the same situation as you, from helpdesk to hardware/software support, to server admin role (currently systems admin.), but what I realized is as for me I don't want to stay at admin level forever, therefore since I don't have bachelor degree its even harder to get into management, I decided go back to school and get my management degree, this way I will be more visible to management position with 12 years of technical IT experiences.

 

I am joining you in the list of people wanting to go IT and trying to decide how to go. I making the change after losing my job. Now I already have a bachelor degree in a unrelated field so I going back to school to get a some stuff in computer IT.

I am going to general route and hoping to get into a small the medium company as one of the people in the IT deparment since they will value jack of all trade type.
From there I will start becoming more specialized in the areas I want to move on into. I just have to get my foot in the door first.