Simon, who is , was born in Dar-es-Salaam, ('the place of peace' in Swahili), the youngest of four children, and then travelled a great deal with his family, as his father was working for UNESCO.
After completing his secondary education at Stonyhurst College, Simon spent some time working with a North American Jesuit in a parish in the hills above Kingston, Jamaica. This experience, being close to those who had very little material possessions and who had an undaunted faith in God, encouraged him to study theology when he returned to England. He spent three years at Pembroke College in Cambridge, and then after working some time with the sisters of Mother Teresa in north London, he trained as a social worker at York University.
After qualifying, Simon worked in Brixton for the Catholic Children's Society, trying to prevent homelessness among 13-18 year olds and, wherever possible, trying to bring about reconciliations between these young people and their families. This work brought him back into contact with the Society - his boss was a Jesuit (who is now the Provincial) and the local parish in Brixton is served by the Society. This renewed contact and friendship helped him to reconsider the life of St Ignatius and of the Society and, after some time of spiritual discernment, he was accepted into the novitiate in 1993.