Stephen Dailly studied English Literature and Classics at Keele University before teaching in a variety of schools and colleges for eighteen years.
In the late 1990s he began volunteering in prison chaplaincies and has worked with prisoners before and after their release, in various capacities ever since. In 2013 he was involved in starting Walk Ministries.
An evangelical Christian, he is a member the Dove Church in Uttoxeter, Staffordshire where he regularly speaks and leads worship.