The sense of belonging for educators is inconsistent across public high schools in the United States. Recent increases in restrictive legislation and shifting societal attitudes have forced many individuals to conceal aspects of their selves, creating long-term ripple effects on students, staff, and communities. This qualitative study examined how educators in public high schools experience belonging in their workplace. Participants, including teachers, school counselors, principals, and assistant principals, were recruited through snowball sampling, professional networks, and social media groups supporting diverse educators. Participants in this study were selected based on their roles as public high school educators (i.e., teachers, administrators, counselors, professional support staff) from the Mid-Atlantic region (i.e., New York, New Jersey, Pennsylvania, Delaware, Maryland, and Washington, D.C.). Analysis of 15 participants’ experiences revealed several key findings: school leaders set the tone for how educators connect with their workplace and colleagues; fear of others’ perceptions often leads to guarded interactions with colleagues, communities, and supervisors; external factors inhibit a sense of belonging and impact educators’ ability to bring their authentic selves to work; educators believe their authenticity impacts students, which supports teacher-student connections and empowers teachers to remain visible as role models; despite challenges, educators offer actionable recommendations for school leaders to support authenticity and foster a sense of belonging.