The paper analyzes mutual relationships between three processes from the title on the example of three paintings by Slovak painter Rastislav Podoba. Analysis of the painting Observation from 2011 leads to the need for a deeper examination of the character of relations between observation, painting, and interpretation. The central problem is the problem of observation which leads to questioning the place and the role of theoretical reflection in the creation, experience, and perception of the work of art. The standard philosophical approach to interpreting as an ascription of meaning is questioned. Finally, the paper proposes a different approach to interpretation that could better explain running processes in analyzed works.