We all have our own approaches to these issues. I will contribute my 2 cents. I am saddened by the push to make kids specialize at an early age. Those who do so to try to get their kids into the professional ranks will fail most of the time and risk causing their children to lose the love of the game. But in many communities if a child wants to make even a high school team,they have to specialize pretty early. My solution was to leave it up to my kids. My daughter was crazy for music, theater and dance and was pretty good. So I attended a lot of concerts, plays and recitals. My son, who is pretty small, loved golf from an early age. Early in high school he realized that while he had a good swing, he would have to drop his other summer activities (spending them in the north woods) to have a chance. I left it up to him and he chose to play tournaments. He ended up a pretty good player who could have played at lower level DI or below. Instead he made a long term choice to focus on his studies which is where his best talents lie and he has one year left in law school. For me, the important thing was that after consulting with his parents and coaches, he made his own decisions. Making those decision was part of growing up and while part of me wishes he could have enjoyed a broader experience, he learned a lot from having to determine what he wanted to do.
For me. that is a key to the parenting process. Barney, I suppose I have been pretty lucky. I too never wanted to disappoint my Dad, or my Mom for that matter. I still don't and I am almost 10 years older than you. But that desire arose not out of any fear, rather it came from a mutual love and respect. As I grew older we had our disagreements; mostly over politics in the late 60's (he eventually came closer to my way of thinking although I moved a little too) but we retained our mutual caring and have become best of friends while retaining a father son relationship. All this despite the fact that Dad never saw many of my games because of an extremely busy work schedule. I knew he was interested, he just had other things he had to do to build a business and take care of us.
I have been luckier than Dad in that my schedule has been more flexible so I have been able to watch my children's activities. I have had very few rules, I guess I was lucky to have kids who understood that if they were well behaved they would get more leeway so I didn't have to spell the rules out. I learned that from my folks. When the kids got close to the line, we would talk our way through issues so that they would understand why their behaviour might be troubling. The idea was to instill an approach that would allow them to figure out problems in a caring and ethical manner. I suspect that they don't want to disappoint me or their mother. But more importantly, they don't want to disappoint themselves. We are also good friends, not in the way they are with their peers, but good enough so that we can go to ballgames, play golf etc and have real conversations and engage in good natured ribbing without any prompting. Like I said, I am a lucky guy but I would like to believe I gave myself a chance to get lucky by encouraging my kids to make decisions that they were capable of making at any particular stage in life and by being supportive of them in their pursuit of the things they loved. They still have a long way to go and I only hope I can continue to support them and enjoy the journey.