Are you going to go through this dilemma for all your developers when they consider jumping ship at various points of their careers? Probably not, so you're al

Are you going to go through this dilemma for all your developers when they consider jumping ship at various points of their careers? Probably not, so you're already doing something special for this person. Since you seem to be intent on being a robot with regard to personnel decisions, there is only one question to answer: Is your company going to go down the tubes if he/she leaves? If so, do what you can to keep them. If not, cut ties and move on. As an aside, I find it humorous that you're consulting an anonymous online message board for this type of advice. Surely you've handled more difficult problems than this in growing to a 50 person company?