This chapter examines how different types of situations in preschool activities shape children’s models of reality and contribute to personality development. It identifies three key activity types—learning, play, and project-based learning—each corresponding to a distinct situational model. Learning unfolds in normative situations, where children engage with cultural artefacts according to established rules, constructing models of the world based on social norms. Play involves imaginary situations, where symbolic modeling allows children to explore meanings, emotions, and relationships, forming semantic representations of reality. Project-based learning introduces creative situations, combining cultural and personal meanings in the child’s model of the world. An empirical study with 215 preschoolers revealed that while play supports self-regulation, project-based learning provides emotional stability. Both contribute to speech development. The findings highlight the importance of integrating all models of reality, emphasizing the role of acquiring social norms, cultural meanings, and personal agency in preschool settings.