[2] Taiwo commenced his teaching career as the headmaster of Sagun United School, Oru-Ijebu, a government-assisted institution in 1932.
[3] He was the first African Principal of Edo College, Benin City and became Permanent Secretary, Ministry of Agriculture & Natural Resources in the former Regional government of Western Nigeria;[4] He was called to the Bar at the Middle Temple (Inn of Court), London on 4 February 1964, and enrolled as Barrister-at-Law and Solicitor of the Supreme Court of Nigeria on 3 July 1964.
Taiwo worked with the Western Nigerian Government between 1960 and 1966 when he served variously as Administrative Officer, Inspector of Education and ultimately as Permanent Secretary, to the University of Lagos where he spent 11 years, private legal practice and authorship of books.
He was also appointed as Pro Chancellor and Chairman of the Governing Council of the University of Ilorin on 1 September 1990 and became a Solicitor and Advocate of the Supreme Court of Nigeria.
[7] Taiwo was a prince who hailed from the Olumota ruling house of the Oba Oloru of Oru, Ijebu, thus making him an Omoba of the Yoruba people.