The present invention discloses a system and a method providing for a progressive transition of the holdings within a portfolio that takes periodic gains as the market rises and utilizes a portion of those gains to buy back in as the market falls while providing for a gradual reduction in the volatility of the portfolio. Many existing systems only allow one stop-loss or trailing stop-loss value to be used resulting in the complete liquidation of the investment once the target value is breached while some newer systems involve the use of two or more different protection levels per security, some of which may adjusted to reflect market performance and some of which may be essentially fixed. As will be appreciated by those in the art, the various systems may be adjusted to reflect the financial goals and risk tolerance of particular clients.