Abstract: A lifestyle management tool may determine a first work optional date, wherein the first work optional date is a date in which a user's retirement income is greater than a user's expense. The tool may also receive past health characteristics of the user, current health current characteristics of the user, and future health characteristics of the user. The tool may further derive an estimated date of death of the user based on the received health characteristics of the user. The tool may also calculate the net present value of the user's income less expenses each year from the first work optional date until the estimated date of death. The tool may also determine a second work optional date, wherein the second work optional date is a date in which the net present value of the user's income moves from negative to positive.