He said the biggest change was the jump in the amount of paperwork. Over his career so far there had been countless memorable moments, but Mr Drake said two in particular stood out.
The greatest compliment he had ever received came about 20 years ago from a fourth-form boy who was annoyed with him after he had dealt with another student who had committed a "minor crime in class".
"He was a bit fed up. 'The trouble with you Mr Drake', he said, '[is] that you can see the good in everyone'."
The second moment that stood out was the "narrowest escape" he's had from a major accident, when in the 1980s he and a class full of students narrowly avoided being caught in a lahar while out in the Western Bays.
Mr Drake said they managed to get out of the area with "30 seconds to spare" - something he put down to a combination of good luck and good sense. Now, with many years more in the teaching profession behind him than he planned, he is as keen as ever.
Mr Drake said he had fallen into the habit of wanting to see how each new bunch of third-form students grew and progressed during their time at college.
"Five years is roughly 250 weeks so it's only really 250 weeks between a nervous 12-year-old and a fairly accomplished Year 13. They change almost every day."
He said because of his longevity he had become the go-to person when someone wanted to know something about the school's history, from the position of drain pipes to the way things were done 20 or 30 years back.
"In a way you are the memory of a school."
Mr Drake said he was monitoring himself, and had other people monitoring him, to make sure he didn't stay in the job too long, but said there was always room for "one or two" long-standing staff.
"I'm one of those people who tend to value endurance. I don't feel I'm quite finished yet."