You like working with users, and designing software - that sounds like the descriptiong of a Product Manager, sometimes also known as a Systems Analyst. By whatever title, the role is one of interfacing with customers/clients to identify their needs that your employer's software doesn't yet address. Your software development experience will allow you to recognize the feasibility/usability, etc. of the ideas the users suggest - because often users suggest solutions, rather than presenting the problem and letting the vendor identify the solution. Best, of course, is when vendor and customer work together (iteratively) discovering (perhaps using prototypes) the best design/architecture/UI/etc. that solves the problem they have. Your preference for working with users suggests that this role of "helping the user to understand the problem they are really trying to solve, and designing an appropriate solution for it" would be fulfilling for you. Product Managers & Systems Analysts are often office-bound. If you think you'd like to be out on the road then Technical Sales is the equivalent position. A Technicals Rep partners with another (non-technical) sales person; the non-technical rep does the work of opening doors, haggling, negotiating, etc. At some point in the process the Technical Rep is introduced into the conversation to present the actual capabilities of the product being sold, and to demonstrate how they would solve the prospect's needs. None of the above would require a new education. Of course, if what you really want is to go back to college, then that's another thing. HTH, Chris