This definition is predicated upon by the term Life of Riley. The Life of Kibbie is a more evolved state of the Life of Riley. The evolution is: an individual who lives the life that everyone around them wants to; but for one reason or another the jealous party cannot live this life, usually a job or "real world" responsibilities are holding them back. This is a balance that one has to achieve over time, usually after their 40th birthday. This is a keystone in the compliment world.
Deaner: Yo Bob what are you up to tonight?
Bob: I am going go see Terry, he is back in town from his travels around the world.
Deaner: Did you hear Terry just got a new motorcycle in August and traveled to Chili to ski and surf?
Bob: Man oh man, does that guy live the Life of Kibbie or what?
Deaner: Yes Bob he certainly does.