This chapter considers the impact of age together with gender in the working life and career development of early to mid-career women managers. The authors’ analysis of interview data with women managers in Finland and Scotland/United Kingdom found that direct and indirect discrimination intersected across women’s ages and employment sectors, with similar experiences in both countries. Although many organisations profess to be working towards diversity in the workforce, women were regularly dealing with discrimination, based upon their age and gender. Issues included being a woman supervising men, to potentially becoming pregnant, taking maternity leave, becoming a career, and reconciling domestic, family and working life. The day-to-day and longer-term experiences of early to mid-career women are often ignored, taken for granted or considered to be addressed through human resources policies. Thus, in addition to existing legislation and national and organisational policies, there is a need for transparency in pay and in terms of the issues presenting challenges for women’s careers.