Entrepreneurship researches have been curiously silent on luck since luck, itself is elusive and cannot be systematically quantified in any meaningful measurement. An explicit and systematic evaluation of where luck is situated along the spectrum of certainty to absolute uncertainty will be undertaken in this paper. Exploration on the social construction of luck, effect of luck, human interventions relating to luck; the discussion on the operationalization of luck will open potentially rich veins of theoretical inquiry premising on quantum uncertainties, chaos theory, Heisenberg uncertainty principle and Weick’s sensemaking. Heisenberg uncertainty principle or Knightian’s uncertainty or the chaos theory, they are not competing alternatives and irreconcilable as they are not dealing with the same aspect of the indeterministic phenomenon. This paper will explore the indeterminacy of luck along the processual pathway of entrepreneurial venturing. It concludes by offering a compelling proposition on opportunistic and propitious timing with regards to the eventual rewards.