Born Orthodox by his princely origin of the Obolensky Russian family of the Rurik Dynasty.

In exile he was converted to Catholicism and became a member of the Russian apostolate abroad.

In 1901 Obolensky graduated from the Faculty of Law, Saint Petersburg State University.

In his career Obolensky was a State Counsellor (1914), member of the Ministry of Internal Affairs (Russia) (1915) and Chairman of the Special Committee for the Struggle against high prices (1916).

Together with his son, Sergei Nikolaevich Obolensky adopted Catholicism, and became a member of Russian apostolate.