He took a break from his primary education to work as a shop keeper from 1968-1969 in Agbovile, Ivory Coast, in order to cover tuition for his secondary education at Baptist High School, from which he graduated in the year 1975.
[1] Next, he attended The Polytechnic, Ibadan for two years and earned an Ordinary National Diploma (OND) in Mechanical Engineering in 1978, after which he spent a year working at the Nigerian Bottling Company run by Coca-Cola as a Mechanical Supervisor.
[1] In 1985, after his National Youth Service Corps year, Oriolowo briefly taught at Bishop Onabanjo High School in Bodija and at Ile-ogbo Anglican Church Grammar School.
In 1991, he was hired as the Principal Irrigation Engineer in charge of FADAMA I Coordination until 1992.
[5] Prior to his election, he was the General Manager of the Osun State Agricultural Development Corporation from 2007 to 2013 and Permanent Secretary of Ministry of Water Resources, Rural Development and Community Affairs of Osun from 2013 to 2016, and parent to enikasaye olanrewaju samuel.