As the parent of a Millennial that has carved his own niche and is now beginning to enjoy financial rewards, I can tell you what worked for him:  we told him that we expected at least an 80% average in school and we didn't ride or coddle him.  80% was good enough as I also wanted him to have a life outside of academics.   It was up to him to figure out how he was going to do this.  We didn't push him in any particular direction.  We didn't expect him to work, except for summers.  We felt that school, hobbies and social life were his 'job'.  We provided him with enough money to have bit of fun and a bus pass - no driving him here and there.  He bought clothes at thrift shops and loved it.  The fruits of our hands-off approach is an intelligent, hard-working successful adult.  He would be the first to say that not everyone is the same and that not everyone is meant to be self-directed.  As a society we need to support all personality types, not just competitive entrepreneurs.