CTBBALLDAD and FENWAYSOUTH pretty much summed up what I recommend to players your son's age. The original OP referred to "me" which is fine for you to play "what ifs" as long as you don't focus on it at this stage. It is important to have your son figure it out on his own and once he does you be there for support and guidance. No matter how much you want it, if son isn't 110% committed and driven, he can't go through the motions just to appease his parents (unless a super stud). I used to sit in the stands and listen to some parents describe how they have high school then college then minors all planned out for their son. In many cases these are the same parents who put so much pressure on their sons to succeed and play at an elite level. Many of these players hung up the cleats during high school or upon graduation because they didn't have the drive and/or talent to continue. I often told others that when the day comes where my son decides to move on from baseball, that's it, it's over. Now and through high school is an excellent opportunity to bond as father-son where a shared common interest can be discussed between 2 "adults". Enjoy these times and watch baseball as a game, not an occupation. If fortunate there will be a time for that in the future