The paper describes the huge loss of skills and experience that will accompany the retirement of the baby boom generation. The problem can be mitigated by making longer work more attractive through offers of part-time employment and longer vacations. Unfortunately, a number of private practices and public policies have evolved over the years that encourage early retirement and make it challenging for employers and employees to negotiate flexible, partial retirement arrangements. Private and civil service defined benefit pension plans often penalize working beyond the late 50s even though they specify an official retirement age of 65. High health insurance costs for older workers also curb employment opportunities. The combination of tax law, IRS regulations, ERISA, and the Age Discrimination in Employment Act create complex barriers to partial retirement that are not insurmountable, but can only be overcome with great effort and the risk of litigation. The authors make a number of suggestions for changing regulations and for new legislation.