The classification of financially at-risk is an expansive term that fits the personal profile of most individuals when it comes to the conditioning of their attitude toward money management, particularly in the planning and investment of that money for the achievement of long-term goals. In the case of this thesis, we focus primarily on those who have made a career in professional athletics and entertainment. The behavioral finance tendencies of these two industry professions are widely regarded as insufficient and often damaging the to the longevity of achieved financial security. This ideology stems primarily from an environment where individuals enjoy rapid wealth accumulation in a highly competitive and constantly transitioning role within their respective crafts. The subjectively common behavioral shortcomings of these world-class athletes and performers and uncertain day-to-day security of the professions which these at-risk individuals possess make for highly unfavorable circumstances when striving to achieve a lifetime of income and a secure retirement. In examining individuals of these classes who have faced grave financial hardship, this thesis will serve as a basis for identifying measures to recondition problematic behavioral tendencies that ultimately cause disengagement from a prudent financial plan. Therefore, this thesis will also serve as a framework to determine what investment strategies will complement the behavioral modifications financial planners strive to instill in these individuals, so that professional athletes, celebrities, and financially at-risk professionals alike may achieve higher probability of creating financial freedom through the engaged execution of a goals-based financial plan.