This article focuses on the Czech pension system and its goal is to set limits and discuss options for resolving challenging periods that will arise during this century. Considerations are aimed at using fiscal and pension policies, as demographic projections start to improve the situation again around 2065. The article explains the difficulties with the principle of solidarity, demographic development and pension indexation. It analyses possibilities of parametric adjustments of social insurance (retirement age, insurance rate, replacement ratio) and considers ways of transferring pension expenditures within public budgets. By appropriately configuring the compulsory pillar and the optional options in the voluntary pillar, it seeks a solid coverage of the pension entitlements of the population. The factors influencing social insurance are divided into endogenous and exogenous. It stresses the importance of participation in the pension system and the level of employment. The findings are that we need to design and implement better pension pillars where pension contributions will be paid — while creating a fiscal plan to cover the difficult (but transitional) period ahead.