This dissertation examines how individual characteristics such as gender, education or motherhood status interact with context characteristics such as the location and intensity of care, the structural characteristics and skill requirement of an occupation to create heterogeneity in health and work outcomes. The first chapter examines whether the associations between caregiving and mental health reflect the heterogeneity in caregiving experiences. It explores whether differences in care context (location and intensity of care) and caregiver characteristics (gender and relation to care recipient) impact caregivers' health. Using a large nationally representative sample of the British population and individual fixed-effect models, I find that 1. caregiving is a stressful social role 2. care intensity is a crucial dimension of variation in the relationship between caregiving and mental health 3. the location of care interacts with care relations only for the less intensive caregiver 4. there is a gradation in the negative association between caregiving activities and mental health by care relations and 5. female caregivers are more susceptible to role overload and role captivity. The second chapter focuses on occupational characteristics as an understudied pathway that may explain mothers' return to work after childbirth. I test the overarching hypothesis that specific aspects of occupations, which directly relate to tangible constraints and advantages influence mothers' decisions regarding whether and when to return to work. I also formulate and test a theory of resource substitution which implies that occupational characteristics may buffer the absence of paid maternity leave on the return to work after childbirth. Using the NLSY-97, logistic regression and discrete-time hazard models, I find that occupational characteristics introduce heterogeneity in mothers' return to work. The results suggest that structural aspects of the work context are potential pathways of work re-entry and can both facilitate and hinder the return to work after childbirth. Factors such as autonomy, caring demands, and low physical demands can positively impact a mother's ability to effectively manage competing demands. Conversely, authority in the workplace may act as a factor that pushes women back into work. I also find evidence for the resource substitution hypothesis between paid maternity leave and autonomy and caring demands respectively. The third chapter examines how occupational gender essentialism and the gender wage gap are linked across a continuum of gender-essentialized occupational skills. I investigate if the wage premium for skills differs by gender when those skills are highly gender stereotyped, and if education moderates this relationship. Using data from the NLSY-97, results of individual fixed-effect models show that the return to skills is heterogeneous, especially for women, and differentiated both by college credentials and by the nature of the gender-stereotypes skills itself. Higher levels of gendered occupational skills are generally protective for women with college degrees, and compounding for non-college women.