Paradox theory has strongly advanced the understanding of organizational both/and approaches but says surprisingly little about their relationship with the “either/or”. We argue that the relationship is a paradoxical one because either/or responses enable both/and ones, and both/and responses exclude either/or ones. Using Luhmann’s theory on decisions, we develop a process model, apply it to concepts of ambidexterity and introduce self-reflexive approach that addresses competing demands and the paradoxicality of decisions. Our main contribution is to conceptualize the paradoxical relationship of “either/or” and “both/and”, to introduce the distinction between single decisions and approaches to manage competing demands, and thereby address the potential bias towards “both/and” in paradox literature.