Transgender individuals go through their intrapersonal differentiation between covert “I” (expressed gender) and overt “I” (assigned gender), often unnoticed by family members before their coming out. Consequently, their coming out rockets anxiety in the family system and the process of differentiation of transgender parents seem to go through its unique path to search for equilibrium. Recent social and clinical studies about transgender parents have paid attention to the experience and challenges of the gender transition process, social pressure, acceptance of transgender individuals in a parenting role, and readiness of families to cope with the transition of a parent (Bischof, Warnaar, Barajas, & Dhaliwal, 2011; Chung, 2016; Di Ceglie, 1998; Freedman, Tasker, & Di Ceglie, 2002; Haines, Ajayi, & Boyd, 2014; Hines, 2006; Theron & Collier, 2013; Veldorale-Griffin, 2014; White & Ettner, 2004, 2007). No research study has attempted to explore the essence of transgender parenting and the related self-differentiation process (Bowen, 1978; Kerr & Bowen, 1988). In this research, I intended to address this gap in knowledge by utilizing a heuristic phenomenological research design to explore the essence of parenting and self-differentiation of transgender parents. I used interviews with ten transgender parents, both females, and males, to embrace the elements of the lived experienced. The first conducted heuristic analysis revealed five emerging themes: Selfish Unselfishness: Becoming Me; Relationship with My Close Family: It is About Respect; Battle of Emotions: Do the Right Thing; Competence, Confidence, and Legacy: This Is How We Do It. Or Not; and Life Satisfaction: Welcome to My World. The second, qualitative data analysis, brought evidence of these qualities of self-differentiation: Balancing Individuality and Togetherness; Balancing Thoughts and Feelings; and Self-differentiation in the Expressed Gender.