Examining the Polish and Argentine political and economic transitions, I formulated a means to monitor concurrent transformations diachronically by specifying the constitutive elements of democracy and capitalism and measuring each value annually. In each country, democracy and capitalism can be characterized yearly as particular value combinations. Plotted diachronically, these combinations form transition trajectories. I developed hypotheses about pair-wise relationships between values and simulated maximally different trajectories annually. Applying this methodology to the Polish and Argentine data, I evaluated two oft-recommended yet unheeded policies . The first, restricting elections, is disadvantageous if there is popular transition commitment, immediate economic reform, and few powerful opposition groups ; the second, initial profit-making, may hinder democratization, but nevertheless be worthwhile with democratic commitment, economic stability, minimal reform opposition, and adequate state reform capacity. Establishing democracy and capitalism simultaneously is possible and advantageous, while instituting capitalism without democracy may be deleterious