One of Pickering's students at Montgomery Bell Academy, Tom Schulman, later wrote the script for the film Dead Poets Society, basing the pedagogy of Robin Williams' character very loosely on Pickering's eccentric style. Pickering has eschewed publicity raised by the film and has since regarded the unorthodoxy of his classroom behavior as more goalless than that depicted in Dead Poets Society, in which unorthodoxy is employed deliberately as a way to preach the values of non-conformity and carpe diem. Instead, Pickering has commented that "I did such things not so much to awaken students as to entertain myself."[6] Pickering has often considered his teaching style purely purposeless and impulsive, and he criticizes those who have subsequently asked him about his philosophy on education, responding that people, regarding such large social questions, have trouble with "the realization that mostly it's all meaningless. I don't know why people want answers."[6]
Pickering's writing has been characterized as equally sporadic, meandering, and amusing, with a common teaching and writing guideline of "You have to lie to give the illusion of the truth."[7] His non-fiction work typically takes a humorous tone and revolves around the everyday absurdities and pretensions of civilization.[1] Regarding his writing process, Pickering has said:
I tie all kinds of things together because I like to drift. That's the way life is. Some folks don't like that. [...Visiting writer Scott Sanders] talked about all the tools he could use in the books. So, I wrote an essay called "Tool Less" because I can't use any tools. [laughs] So I wrote about that and I proved that the people who couldn't use tools were more flexible. They were very nice people. People who used tools thought that things could be made and fashioned to last. People who didn't use tools knew that nothing lasts so they were not zealots of any kind. He thought I was a complete savage and a fascist at that. [laughs][3]
^"Pickering to Deliver Commencement Address at Oglethorpe University"(PDF) (Press release). Atlanta, Georgia: Oglethoripe University. April 15, 2002. Archived from the original(PDF) on July 17, 2012. Retrieved 2015-03-04. Pickering will deliver the commencement address, "This Great Gift," and will be presented with an honorary Doctor of Letters degree.