Music shaped Brailey's life from an early age, leading him to a career that spanned both military and civilian performances. Before attending music school, he joined the Pier Pavilion Orchestra. Initially performing in hotels, he later joined the Royal Lancashire Fusiliers as a musician, was promoted to lance corporal in 1906, and spent time in Barbados, before leaving the service prematurely in 1907. Back in London, he continued to refine his abilities as a pianist, eventually finding work aboard ocean liners. By 1911, he had performed on ships such as the RMS Saxonia and the RMS Carpathia, where he met fellow musician Roger Bricoux. Both later joined the White Star Line through the music agency C.W. & F.N. Black, and became part of the Titanic’s orchestra. He boarded the ship in Southampton on 10 April 1912 as a second-class passenger.