Hon. Timbo spent his early formative years moving between Murray Town, Cline Town/Kanikay and Bellair Park. At the early age of one, Hon. Timbo, his siblings and their mum, moved from Murray Town to Cline Town/Kanikay, in the eastern part of Freetown, where his maternal grandparents lived in a humble abode. There, he started his kindergarten education at the J.S. Momoh Kindergarten school (now called John F. Kennedy Memorial School). After spending a year there, he was transferred to the King Hermann Preparatory School (now Kings Independent School). When his father was appointed a Court of Appeal judge and moved to the judges’ quarters at Bellair Park, they all relocated there and then he and his siblings got enrolled at the Mereweather Preparatory School at Joko Kenyatta Road. He studied at that school until standard/prep four and his mother, again, transferred him to the Tower Hill Municipal School where he sat to his National Primary School Exams (NPSE) in 1996.

He gained admission into the Sierra Leone Grammar School where he pursued his secondary education and sat to his senior school exams (WASSCE) in 2003. He spent six years at the school and served as a school prefect, a house captain, president of the Integrity Club, a member of the school’s quiz team and a performing artist for both the french and drama clubs. He was a perennial best performing pupil in his class. During the political interregnum in Sierra Leone between 1997 – 1998, he and his family fled to the Republic of Guinea and there he attended the Conakry International Academy.

In 2003, Osman was admitted to study law at Fourah Bay College (FBC), University of Sierra Leone, and in 2007 he graduated with a Bachelor of Laws. During his time at FBC, he was elected to serve as a member of the Students Representative Council (the Students Parliament) – [therein, he was also elected to serve as the Council’s clerk by his peers], contested for the position of Secretary General of the Solomon Caulker Hall (an election which did not hold), was a member of the Human Rights Clinic, a member of the Law Society and a comrade of the Auradicals Club.

Upon completion of his undergraduate studies, he proceeded to the Sierra Leone Law School, sat to his Bar Final Exams and was called to the Sierra Leone Bar in October 2008.

He also holds a Master of Laws degree from the University of London, several certificates in Public Private Partnership Investment and International Law from the Institute of Public Private Partnerships, USA and the United Nations Office of Legal Affairs, respectively.