I'm the owner of a small business (very small, 3 people). I recently brought my two contractors on as employees after paying them as contractors for a year. A month later one of them asks for a raise, then informs me that he's planning on going back to school in about two months. Yes, in the same sentence. He hadn't been officially accepted, but wanted to let me know. My original plan was to keep him as an employee until he went back. Then, put him back to contractor status and give him work as-needed. I started setting up interviews and preparing to transition his projects to somebody new. I informed him that he would not be getting a raise and needed to know what his last day in the office would be. I then receive an email and he tells me it turns out he may not be able to start in two months like he thought and now it may not be until next spring or fall. So far he hasn't told me either way. What do I do? Stick with my original plan? Keep him on as an employee until next spring or fall? Obviously his interests are no longer with my company and productivity has been slowing down, etc. Who's to say he won't change his mind again or go back earlier than he's telling me? I feel like at this point, with the flip flopping, I can't rely on him to be here for another 6 months and if I need to replace him in 6 months why not just do it now? Are there any unemployment implications I'm not thinking of if I put him back to contract in two months? I doubt I'll be able to give much if we find a suitable replacement anyways.