Survey findings indicate that members of the Silent Generation--those born between 1933 and 1945, and perhaps the last ones to rely heavily on a defined benefit pension plan--feel confident that they will have enough money to live comfortably to at least the age of 85. Yet, many are at risk of outliving their retirement assets. They overestimate their Social Security payouts and the likelihood that they will work in retirement, and they underestimate their postretirement expenses, especially health care. Many lack safeguards against overspending and do not understand their longevity risk. The Silents' experiences in preparing for and living in retirement may offer some valuable lessons to be learned by the baby boomers and the generations that follow as they plan for a financially secure future.