GREAT topic, JBB! And definitely, as you said, not an easy one.
BTW, HShuler, for reference, JBB has two sons in the pro ranks currently if I'm not mistaken. So, he has certainly been down the full road as much as anyone. But he is generous enough to continue bringing insight here and occasionally throwing out these thought-provoking topics.
Of my three kids, the youngest son was the only to pursue sports beyond HS. He is currently a college senior and would certainly be considered by most to be an over-achiever in baseball.
I tend to be very pragmatic in my parenting and coaching approach. As I think through how I have guided my own kids through their career direction, this certainly applies. However, when it comes to the youngest, his lofty goals were in the arena of my specific interest and passion (sports/baseball). So, for him, I was much more careful to walk that fine line as to not disrupt his far-reaching dream and at the same time, keep him grounded with reality. I struggled with this often. His size/ skill set did not equate to beyond college and, at some point late HS or early college, I think he was able to figure that out. But his 6th tool could play anywhere and that kept the dream in play. I think, with the kids I coach, I tend to be even more pragmatic with directing those with next-level aspirations (so that I can provide sound recruiting path advise) but I still try to allow for (positive or negative) 6th tool and growth potential.
I think so much of this process applies to all career / schooling / athletic / philanthropic / arts decisions we go through with our kids as well. Is it a pipe dream? Is it a far but reachable goal? Should it/ could it be a career? How do we advise our kids? Bringing knowledgeable outsiders with personal distance for a pragmatic viewpoint has much merit and should always be part of these big decisions. But also, someone close to the person (parents/ close advisors) should factor in heart, work ethic, passion, street-smarts, ability to push through obstacles, competitive nature, etc. (6th tool). I think it is important to take interest in each of our kids' interests and take lead on the "believer" team. With both sides covered at the detail level, smart decisions can be made. Usually. I don't know. It's still hard.