Personal growth occurs with life experiences and most importantly handling and reflecting on negative life experiences teaches us more (Mickler & Staudinger, 2008; Staudinger & Gluck, 2011). The distinction between personal and general wisdom is based on the differences in the development process and happiness-satisfaction distinction. This article argues that personal wisdom development involves pain and suffering (Staudinger & Kunzmann, 2005) yet feels more satisfying in retrospect. The wisdom literature so far is focused on understanding the concept which is majorly correlational, and recommendations are to study the idea experimentally so the concept can be brought to the intervention arena. Therefore, the present study attempts to explore, 'the effect of personality disposition (emotional regulation, reflectiveness, openness to experiences and action orientation) in decision making and affect handling (regret handling) as an indicator of wisdom. Precisely, 1) if people with different personality disposition differ in the choices, exploring the alternatives and handling regret in the face of failure; 2) if people with higher action orientation chose a risky option and if this choice results into failure how do they handle and finally, 3) does personality disposition predict regret handling. The objective was explored by applying SAWS questionnaire, Action Orientation questionnaire, and share the market task. The results suggested that openness to experience, and preoccupation vs. disengagement, hesitation vs. initiative dimension of action orientation significantly influences choice-making and comparatively less regret experience. Additionally, individual high on openness and action orientation explore more alternative, choose risky options and report less regret if faced with failure. The common explanation for less regret after failure may revolve around the theme of 'at least I tried'. The mediator regression analysis suggested that the individuals with initiative tendencies regret less, similarly, people with an openness to experience also regret less than their counterparts. However, individuals with high initiatives and openness to experience regret more in comparison to people with only openness or initiative tendencies. This experimental evidence confirms the observation that individuals who are open to different experiences and take specific actions to try new things will face more ups and downs and experience more regret.