A series of articles has recently appeared in which implications of second-order cybernetics for the practice of family therapy have been discussed. In this article, we attempt to advance the discussion by addressing ideas that we think have not been adequately emphasized thus far. Specifically proposed are ideas about conditions that might facilitate the emergence of consciously pragmatic strategy informed by the kind of systemic wisdom that delicately balances natural systems without the benefit of human planning. It is argued that a shift in the personal habits of knowing and acting that typically organize individual human experience is required. After attempting to specify what this shift might involve, implications of these ideas for the practice of family therapy and for human action in general are discussed.