Other sources, however, suggest that Calendar dropped out of school on his own free will, influenced largely by his young friends. He joined the Public Works Department (P.W.D.) in 1927 as an apprentice carpenter. By 1930, he had become a qualified carpenter, and he was employed by Pa Alimamy Boungie, an undertaker at Kissy Street. Pa Boungie's undertaker shop used to conduct wake-keeping ceremonies for bereaved families. Thus Calendar would learn coffin-making during the day, and at night he would be among the men Pa Boungie would send to sing at wake-keeping ceremonies.
About this time, Calendar and two of his friends formed a small musical group. They practiced on open grounds, and on-lookers would sometimes give them money. Later, they began getting invitations to perform at weddings, parties and other festive occasions. All of this was just part-time, reserved for evenings, as Calendar continued working for Pa Boungie. Before finally embarking on a full-time musical career, Calendar worked for some time with the Sierra Leone Railway, opened and ran an undertaker shop, and then was employed as cabinet-maker for the United African Company Limited (U.A.C.).
A versatile musician, Calendar learnt to play several different musical instruments including the mandolin, the cornet, rhythm guitar and the trumpet. Calendar's group in the 1940s and 1950s, relied upon a combination of locally produced instruments like the bata (hand drum) and the triangle, and Western instruments like the guitar and the tambourine to produce his distinctive maringa rhythm. In 1951 he was commissioned by DECCA Recording Company to record a song commemorating the launching of the newly introduced double decker buses. The tune was an instant success and Calendar established his reputation as a popular songwriter/musician celebrating contemporary events of the period.
From this point of view, he can be looked upon as a social historian, commenting on contemporary happenings. Calendar's early songs formed part of the dance music of the fifties and sixties, and most of his compatriots will remember the swinging rhythm of the hit song "Fire, Fire". As he grew older, his music became more philosophical and he began to consider himself more as a teacher with the responsibility of imparting the lessons he gained from life to a younger generation.
