In the late 1940s Herbert studied architecture at the University of Manitoba and then worked for Green Blankstein and Russell, (now Stantec). He maintained close friendships with these colleagues all his life. In the late 1950s, Herbert left Winnipeg to attend music schools in London, England, studying voice, with a view to a career in opera. Ultimately he decided that architecture would be a more pragmatic career path to follow and decided to settle in Toronto. While keeping his feet on the ground with architecture he continued to sing in operas, musicals, and choirs, and had a lifelong love of the arts.
In the early 1980s Herbert's friend, Ken Ang, fellow graduate of the University of Manitoba Faculty of Architecture, invited Herbert to join his architectural firm in Singapore. Herbert accepted and in addition to his architectural work, he was quickly drawn into musical circles and performed at the Raffles Hotel on numerous occasions. He eventually returned to live in Toronto and finally moved to Winnipeg in 2010 where he renewed old acquaintances and promptly joined three choirs.