This is an auto-ethnographical qualitative research based on the context of Bangladesh. It is written on the “Hero's Journey Model” (Coaching, 2014) that refers to a complete course of self-development. Being stirred by my own story, I posed to make this study with an effort to unveil certain socio-cultural challenges and taboos in disguise that are liable to stigmatize or, in certain cases, traumatize single mothers and cause them to suffer in their academia and career. This is an attempt to help these mothers cope with the hurdles that they face and find hope in building resilience for stress-free lives. Certain professional, academic, personal, and socio-cultural challenges have been identified through this. A great deal of reasons like wrong social perceptions, cultural restrictions, patriarchy, etc. behind the sufferings of single mothers has also been emerged in course of this study. This overall surfing came up with chief discussions and suggestions to establish a universal platform for their overall transformations. Finally, effective inklings like the formation of help groups, special quotas or extensions of age limits, and special funding for healthcare, study, childcare, etc. are incorporated as recommendations. Keywords: auto-ethnography, qualitative research, hero's journey, challenges, taboos.