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"So where is the line between pushing too hard and letting him make is own decisions? Do I just put my foot down and say this is what you're doing and you'll thank me later? Is this just part of "that age?"
Only you can answer that question because you know your son best. Of course your son would rather play Xbox, watch TV, or surf the internet. As humans, we're all a little lazy and like the easy option. However, you know deep in son heart what his intent is. If it's to play HS baseball, college later, and maybe a shot at the pros, you know it well. As the wise father, you also know the work required to get there. Let me challenge you with this, go the HS track and run 2 miles (8 laps). As it gets harder and harder and your heart is working at full speed, that's somewhat equal to physical/mental challenges that your son faces when working-out for baseball. It's tough doing that day in, day out. That's where he needs someone to keep a boot in his a$$ and positive motivation to keep working towards his goal. We all need that I guess. I know I had to do that for my son and he's now living his dream.