Henry completed his Diploma of Aviation at Basair, with the Commercial Pilot Licence and Multi Engine Command Instrument Rating. He started his aviation career with Broome Aviation in single-engine charter before moving to West Wing Aviation flying the Britten-Norman BN-2 Islander. He then became First Officer with QANTASLink before moving to Cathay Pacific to fly the 777. He returned home to Australia to fly the A320 with Jetstar and then with Qantas.