The purpose of this paper is to increase our understanding of how insights in conflicting concerns can be used as an approach to design for subjective well-being. This is done through examining qualities of a conflict experience across three life domains: food, procrastination, and safe sex. Ten participants from various age groups and backgrounds volunteered for a two-week diary study followed by in-depth interviews. Our findings indicated that there are three layers to a conflict experience: (1) mutually exclusive action alternatives, (2) immediacy of concerns, and (3) elicited mixed emotions. Interaction among these layers revealed three variables that influence people’s choices between two mutually exclusive action alternatives, namely size of the hurdle, awareness of potential costs and gains, and vividness of concerns. Our findings also include individual strategies that people use to deal with conflicting experiences. These strategies inspired three initial principles for designing products that can motivate people to prioritise meaningful goals, fulfilment of which can lead to sustained happiness.