The paper investigates the cognitive determinants of routinization and creativity by means of a lab-in-the-field experiment run at the 20th edition of a mass gathering festival in Italy (“La Notte della Taranta”). Subjects play repeatedly the puzzle version of the Target-The-Two game (32 hands). In hands 1-16, the strategy that is optimal given the card distribution is always the same and it is the easiest to be discovered. Conversely, in hands 17-32, subjects are exposed to games where the optimal contextual strategy may differ from the one with which they have been made familiar. We investigate whether and how, in hands 17-32, subjects remain routinized on the familiar strategy, or creatively choose a different one. We define as “experts” those subjects who played the optimal contextual strategy in the overwhelming majority of hands 1-16. In hands 17-32, we find several subjects playing the familiar strategy even when it is not the optimal one, regardless of whether they are experts or not. This shows that routinization is deep-rooted in the cognitive individual process. Furthermore, routinization pays off only for inexpert subjects: creative inexpert subjects are slower and they fail to find the optimal contextual strategy in several hands. Among expert subjects instead, creative subjects, although still slower, need less moves than routinized ones to find the optimal contextual strategy.