Explaining that he became an artist in childhood because he couldn't do anything else. "My life was a total disaster until I was 20 years old. My one and only ambition was to be a gamewarden, so when I'd finished my education, I went rushing out to Kenya with the incredibly arrogant idea that I was God's gift to the National Parks. It was a disaster. I knocked on the door of the Head Gamewarden in Nairobi and said, 'I'm here, can I be a game warden?' I was told I wasn't wanted. My life was in ruins; that was the end of my career in three seconds flat." "Up to that point, my only interest in art had been as an escape from the rugger field. The game was compulsory at school and I was terrified of it. I couldn't see any fun in being buried under heaps of bodies in the mud and having my face kicked in. I fled into the art department where it was more comfortable and painted the most unspeakably awful painting of birds."
Deflated and homesick, he took a job as a receptionist in a hotel on the Kenya coast; the salary was one pound a week.
"So there I was at Malindi on the Kenya Coast in this hotel. I painted some more bird paintings on plasterboard, and I sold seven of them for £10 each to the
culture-starved inhabitants of the town and paid my passage home to England on a Union Castle steamer."
Arriving home, penniless, he had two choices,Mr Shepherd decided he could either become an artist or a bus driver.
Since he suspected that most artists starved in garrets, life as a bus driver seemed the safer bet.