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India’s education system has often been critiqued for aspects of rigidness, competition, work overload, hierarchic power, and lack of creativity, resulting in feelings of stress and anxiety in students. Interestingly, alternative education approaches have come up in the past few decades in response to formal education, including the rise of unschooling. In this article the journeys of three unschooling parents are analyzed to bring insights into 1) what role stress and anxiety might play in the decisions of Indian parents to choose unschooling, 2) how key advantages and disadvantages of unschooling are shaped and recognized by unschooling parents, 3) how personal experiences of ‘stress’ are appreciated and experienced in Indian unschooling family contexts, and 4) what distinctively different processes are evident in the upbringing process of unschooled children, compared with those existing in formal education systems. Results reveal that a sense of tedium in formal classrooms, as well as a problematization of stress, motivates parents’ decision to unschool. Social pressures and challenges are experienced, yet also welcomed by parents as part of the unschooling journey. The ideas of stress versus distress are examined. Finally, this article reflects on aspects of trust and self-agency, which were found meaningful in unschooling and how to potentially encourage such notions in formal education settings to prevent mental health issues in children and youth.