We propose a novel multi-period trading model that allows portfolio managers to perform optimal portfolio allocation while incorporating their interpretable investment views. This model's significant advantage is its incorporation of the latest asset return regimes to quantitatively solve managers' question: how certain should one be that a given investment view is occurring? First, we describe a framework for multi-period portfolio allocation formulated as a convex optimization problem that trades off expected return, risk and transaction costs. Second, we use the Black-Litterman model to combine investment views specified in a simple linear combination based format with the market portfolio. A data-driven method to adjust the confidence in the manager's views by comparing them to dynamically updated regime-switching forecasts is proposed. Our contribution is to incorporate both multi-period trading and interpretable investment views into one efficient framework and offer a novel method of using regime-switching to determine each view's confidence.