After graduating from primary school, Olakulehin taught briefly as a primary school teacher at Wakajaiye in the Akobo area of Ibadan and subsequently gained admission to Yaba Technical Institute for vocational study in printing and artwork.
[4] In 1959, Owolabi Olakulehin commenced his career at the Ministry of Works, Western Region Government in Ibadan, entering as a third-class clerk.
He subsequently undertook diverse roles and assignments throughout the nation, steadily advancing to the rank of Major.
During his tenure, he assumed various leadership positions, including that of Commanding Officer of the Army Maintenance Regiment in Jos, Kaduna, and Lagos.
[6] After retiring from the army, Olakulehin ventured into entrepreneurial ventures, through FAKOL Nigeria Ltd, a construction contracting firm, Olakulehin Press, (later rebranded as Solid Prints) and FAKOL Bakery in the city of Ibadan.