One effective approach lies in the words of a great Chassidic personality who exclaimed: 'one must establish rules in order to break them!' (No, he wasn't a confused anarchist!) He meant that people should train themselves to live according to particular sets of disciplinary rules and programs for spiritual self-development. However, upon succeeding to do so, one should avoid becoming bound by those rules or routines and to perform them out of habit. Rather, one should maintain self-awareness and, when necessary, 'break' the rules in order to cater to the ever changing circumstances of life.
Without rules and a routine, life is unstable and disorienting. Progress becomes difficult to gauge and one can't see if they are on the right track - after all, without rules there is no track! A routine provides a solid base for life. On the other hand, without change and variation, life becomes dull and monotonous, for the unpredictability and risk of adventure injects much joy into life. It also allows for progress to occur in leaps and bounds rather than gradual successive steps.
Cohesion between the two aspects is apparent in Jazz music where a regular beat and rhythm serve as the solid ground from which musicians temporarily depart and adventure through improvisation and extempore play. Analogously, a skater should first learn to perform tricks properly by setting solid boundaries between each trick, as mentioned above. However, once he's trained himself to perform many tricks proficiently, he mustn't become confined by them.
One must establish boundaries in order to break them: one must skate Jazz.