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This entirely depends on how much you want to make. Foremost, helpdesk consultants in large cities and for corporations usually make $50 - $60K starting and also get full benefits such as 401K, health, dental, etc. If you are looking for a more managerial role you might want to take management certifications so that you can fill a role as an Operations or Business Systems Analysts. If you want to be able to have a more flexible schedule you can do contract or consulting work which runs usually 6 - 8 months per year. However, you are trading off job security for contract jobs if you are planning on doing so.
Please note that the amount of students in computer technology and information technology has jumped significantly. You might find that many more people are applying to the same jobs at entry level. I would suggest that maybe you can join a small company first as a Chief Technical Consultant and then build them a system that can then translate as both technical and managerial success when going after corporations.