This qualitative study explored ex-offender’s community reintegration experiences following a prison sentence. Fourteen ex-offenders from the Offender Alumni Association participated in an in-person in-depth individual interview regarding their current roles, daily routines, living situation, activity participation, and current and future plans. A phenomenological approach using thematic analysis was employed for data collection and interpretation. The emerged themes were categorized under facilitators and barriers that influence healthy community reintegration. The facilitators included visualizing and committing to an ideal future, establishing a daily routine, upholding life balance, and discovering and connecting to external supports. The barriers included impediments to employment opportunities, lack of financial resources, social stigma, regulations imposed by the judicial system, disconnection from social advancements, and addiction to drugs and alcohol. The themes identified from the interviews suggest that current reintegration strategies and programs need to be improved in order to benefit ex-offenders seeking these services.