Career breaks, whether due to caregiving, personal health, or other life circumstances, can have profound psychological effects on women re-entering the workforce. This paper explores the emotional and mental health challenges women face after a career hiatus, including diminished self-confidence, imposter syndrome, anxiety, and workplace reintegration struggles. Social and structural barriers, such as skill obsolescence, gender bias, and work-life balance concerns, further exacerbate these challenges. However, support systems like mentorship, upskilling programs, and organizational flexibility play a crucial role in easing this transition. The study highlights the need for policies that promote inclusivity and mental well-being to ensure a smoother reintegration process. One needs to understand that the role of primary caregiver has been entitled to the women which she plays significantly well without putting any conditions but at the end of the day and back of the mind it is essential to study the thought process and the key challenges that she faces post a career break which is essentially highlighted in the paper.