The article focuses on a interrelation factors around the principles of strategic sustainability or territories and enterprises in a depressive region. Pskov region serves as a case study in the research. Based both on the static and the dynamic approaches in calculating a number of indices and matrices, the authors demonstrate the impact of the social component and of the human capital upon sustainable development. Calculations of the integral index of the balanced developmental dynamics allow to offer recommendation for human capital development on all levels of power, including that of enterprises, to increase sustainability and decrease the level of depressiveness.