Countless creative ideas are constructed while preschoolers play, and are often reflected in their expressions and performance. Various psychological developments can occur during such activities. Some worth mentioning are the transcendence in their logical-cognitive, social-cognitive, and intrapersonal-affective domains, each of which is influenced by the nature of the learning relationship between teachers and children. The meaning of transcendence in this study is neither moral, ethical, nor religious. It is biological, as expressed by Joseph Pearce as “the ability to rise above restriction, incapacity, or limitation”. The transcendence results in a newfound adaptive intuitive sensing that can be developed in both adult and children.  The purpose of this qualitative research study, based on the grounded theory research design, was to derive the indicators of transcendence from the key informant children between the ages of 4-6 years during authentic play in a natural setting self-initiated by the subjects. The environment was in a school context involving both outdoor and indoor play using Gordon Wells’ Modes of Meaning as a research methodology. Another goal was to find out what kinds of play patterns lead children to transcend. Furthermore, this research includes the study of the performance indicators of the key informant teachers using Robert Kegan’s Subject-Object Interview (SOI) to find out how differences in the teachers’ orders of mind affected ways of transcendence in young preschoolers during their self-initiated play. This can be used to determine how teachers, in the Thai social context, should interact with the children to maximize transcendence.