Oladokun was born in 1958 in London, England, to an Irish mother from County Clare and a Nigerian father from Ondo town in Ondo state, Nigeria. He grew up in London and Liverpool. He has also lived in Nigeria and the United States.^{[citation needed]}

Oladokun attended Corinthian Avenue Primary School (now Corinthian Primary School) in Liverpool; a Canadian Jesuit run Catholic high school, St. Joseph's College in Ondo, Nigeria; and the University of Ife (now Obafemi Awolowo University), Nigeria, where he studied History and Political Science from 1977 to 1981.^[4] At Ife he developed a fascination with the media and envisioned a future television and media landscape that included improved professional presentations, innovative programs, and inspirational content.^[5]

Oladokun holds a Master of Arts in Communication from Regent University, Virginia Beach, Virginia, US and also a Doctorate of Strategic Leadership (DSL) degree from the same university.^[6][5]

Early in his career, Oladokun worked at Cadbury Nigeria Plc in various management positions from 1983 to 1986 as Publications Manager, Media Relations Manager, and Acting Corporate Affairs Manager. From 1986 to 1987, he was the Group Public Relations Manager/Spokesperson for the A.G. Leventis Group of companies, Lagos, Nigeria.^[7]

Between 1990 and 2009, he worked in the United States as a news journalist, international TV host, producer, senior producer, and later as a managing producer at CBN International in Virginia Beach. At CBN, he developed and produced a portfolio of international TV programs including the popular CBN World News and Turning Point.^[8]

For almost two decades, along with his long-time co-host Kathy Edwards (née Rucker), they popularised several news and magazine programs, including CBN World News and Turning Point, across English-speaking Africa, the Caribbean and the UK.^{[citation needed]}

During his broadcast career, Oladokun interviewed several global figures including Mohammed Ali, George Foreman, Thabo Mbeki, Olusegun Obasanjo, Ibrahim Babangida, Kenneth Kaunda, TD Jakes, Terry Waite (the Church of England envoy kidnapped and held hostage in Lebanon), Andraé Crouch, Myles Munroe, and Cece Winans. In a 1999 tell-all interview, then Nigerian President Olusegun Obasanjo spoke about corruption, debt reduction, his political ordeals including time spent in prison, forgiveness and his faith in God.^[9]

After 19 years at CBN, Oladokun worked as an international media and communication consultant between 2013 and 2017.^[10]

Oladokun was appointed Director of Communications and External Relations at the African Development Bank Group in 2017.^{[11][12][13][14]} Bank President Akinwumi Adesina credits him with restructuring the institution's communication team and strategically raising the profile of the bank, its operations and development impact. Oladokun retired from the Bank on 31 March 2020.^[15][14]

Oladokun is a media and communication strategist, public speaker, event moderator, TV host, and writer. He has spoken at various events including The Platform Nigeria,^[16] the African Economic Conference, the Africa Investment Forum in South Africa.^[17] and the 2022 Dakar II Food Security Summit.^[18] He moderated the 2019 and 2023 Lagos State Governorship Debate.^{[19] [20]}

• Future of Drone Technology – in Thisday 21 Mar. 2019^[21]
• Africa: Saving Our Languages, Preserving Our Future^[22]
• Mr President: 7 things you must do now^[23]
• Echos of communism: The end of globalization?^[24]
• COVID-19: Why Africa Urgently Needs an Ubuntu Plan^[25]
• Locking down Africa now: There is no time for test runs^[26]
• The End of Social Conventions?^[27]
• Africa: Sports as a Business and a Brand^[28]