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I am in my early 30s. I have a BA in an non-computer science field. Currently I am not working in a professional role and have not had much experience in jobs that might require a college degree. I am intelligent and am a good problem solver. I just have had a pretty rough time getting a career started at a level that is appropriate for a person with a college degree. I graduated in the last recession in an economically depressed region of the country and made some dumb career moves early on. Any way I have always been interested in computers and networking. I am more interested in the infrastructure / hardware - OS integration / System / server admin side rather than the app or web site developer side. I have some experience with programming and have worked with linux / unix / set up websites and set up VPS etc. I have set up unix based routers, gateways, VPNS, firewalls, etc. All as hobby. Not for work. My question is if I want to get into a career as an IT admin, with a long term goal such as ultimately an CIO for small to medium size company or governmental department what is my best application of effort? Should I get an MS in information systems? How is the job market in the field? Are certificates by examination an alternative to an MS? What is the best MS for degree that is relatively easy to get into for some one who is 10 years post his bachelors degree? Is it at all possible to just learn on the job. I would rather learn on the job than get another degree. Any other suggestions?