The Covid-19 pandemic had a profound impact on careers globally, leading to phenomena such as the “Great Resignation” and “quiet quitting.” This chapter explores to what extent men and women in Italy experienced pandemic-related “career shocks” and how these events affected their career attitudes, perceptions of success, and work-life balance. Using data from the 5C Career Barometer survey (2020–2021), 284 Italian managers and professionals were analyzed. The results show that while both men and women faced similar shocks, women experienced more frequent family and health-related challenges, such as the loss of a loved one or difficulties related to children. Women also reported higher levels of social isolation, burnout, and technostress, particularly due to remote work. Despite these challenges, women re-evaluated the meaning of their careers, placing greater importance on work-life balance and financial security compared to men. However, men reported higher levels of career optimism. Overall, the chapter highlights how the pandemic exacerbated gender inequalities in careers, with particularly severe psychological and organizational effects on women.