This paper aims to investigate the multilevel careers of members of Polish regional executives from the first direct election to regional parliaments in 1998 until the end of 2014. Formation of self-government in regions is assumed to have started the process of formation of the multilevel system in Poland. Consequently, political career paths began to be diversified and to take place at more than one level. Among the factors with a critical impact on the specificity of Polish regional careers was the fact that regionalisation was preceded by local government reform (1990), and it was assumed that the local elite would become its natural recruitment base. On the one hand, the challenge to the development of the multilevel system has to be recognised. First, regional politics has undergone rather limited professionalisation (only positions in regional executives are full-time political jobs). Second, the legacy of communist centralisation resulted in lukewarm regional decentralisation in 1998. However, one can observe a certain increased prominence of self-government due to access to EU funds and increased financial autonomy. Positions in regional executive boards, especially as heads of regional boards [marszałkowie], have been seen as increasingly attractive career choices for professional politicians. Therefore, modification of the traditional career model is expected, e.g. some inflow of national politicians into regional boards (from positions in the legislature to executive posts).