The authors study the pecuniary penalties for family-related amenities in the workplace (e.g., job interruptions, short hours, part-time work, and flexibility during the workday), how women have responded to them, and how the penalties have changed over time. The pecuniary penalties to behaviors that are beneficial to family appear to have decreased in many professions. Self-employment has declined in many of the high-end professions (e.g., pharmacy, optometry, dentistry, law, medicine, and veterinary medicine) where it was costly in terms of workplace flexibility. The authors conclude that many professions have experienced an increase in workplace flexibility, driven often by exogenous factors (e.g., increased scale of operations and shifts to corporate ownership of business) but also endogenously because of an increased number of women. Workplace flexibility in some positions, notably in the business and financial sectors, has lagged.