I think my parents did it pretty well.....
encouraged me to partake in something like sports.... but never made me do it... and by giving me support, I grew to enjoy football, and baseball...
when I gave them up Junior year, my dad told me "that's fine your doing that, but were not going to have you coming home, and sitting on your butt everyday... It would be nice to see you get a part-time job"... to which he helped me get one, and then gave me a loan to get a cheap car to get me there and back... I had to pay him back every week till it was paid in full, and if I quit my job, I would either have to get another one, or give back the car....
with friends, I could hang out with who I wanted, but they new who were the bad kids... and ussualy rewarded me for picking the right friends... ussualy by taking us to movies or sporting events...
they let me make mistakes, becuase they always feeled that mistakes and failure helps make a man grow, and causes more growth in character...