This essay explores the relation between worldly orientation and rational comprehension in Kant. Both require subjective grounds of differentiation that were eventually developed into a contextualizing principle for reflective judgement. This kind of judgement can proceed either inductively to find new universals or by analogy to symbolically link different objective spheres. I will argue that the basic orientational function of reflective judgement is to modally differentiate the formal horizonal contexts of field, territory, domain and habitat laid out in the Introduction to the Critique of the Power of Judgement. Assessing which context takes priority will be important in making aesthetic judgements and for applying practical reason to comprehend human affairs.