 Osborn left the D'Oyly Carte company in November 1959, to enter the retail business in Surrey, occasionally directing amateur productions.In 1975, during the company's centennial season, Osborn was invited to participate in the final performance of "Trial by Jury", in which the regular D'Oyly Carte chorus was augmented by fourteen former stars of the company.In 1977 he rejoined the company as stage director for "Princess Ida" for the Sadler's Wells special Jubilee season.