Some philosophers understand the pessimistic model of Schopenhauer like finished product. Pessimistic ideas, issued from the Plato and Buddhism, have been transformed by Schopenhauer in the full-fledged vision of World and human moral. However, this phenomenon or paradigm ought to be not only negative sense, but new positive concerning of pessimism in the strategic management in nowadays economy. That is why this article deals with the attempt of practical adaptation of the system pessimism by A. Schopenhauer as positive model: cautious strategy of behavior. It is used an analogy and the principle of "Maxmin", which is spread on strategic management. The result of such interpretation can also be applied to social sciences and interdisciplinary researches.