ˈæftɚ lˈiːvɪŋ hɪz dʒˈɑːb æz ɐ lˈɔɪɚ, pˈɪkɚɹɪŋ ɐpˈɪɹd ɪnðə mˈɛlbɚn ˌɪntɚnˈæʃənəl kˈɑːmədi fˈɛstɪvəl mˈɪkf ɪn tˈuː θˈaʊzənd tˈuː wɪð mˈaɪkəl tʃˈeɪmbɚlˌɪn ɪn bˈɔɪlɪŋ pˈɔɪnt, ɐ ʃˈoʊ wˌɪtʃ ˈɜːnd ðˌɛm ðə pˈiːs ʌv wˈʊd ɐwˈɔːɹd.
After leaving his job as a lawyer, Pickering appeared in the Melbourne International Comedy Festival (MICF) in 2002 with Michael Chamberlin in Boiling Point, a show which earned them the Piece of Wood Award.