pˈɪkɚɹɪŋ wʌz bˈɔːɹn ɪn mˈɛlbɚn ænd ˈɛdʒuːkˌeɪɾᵻd æt sənt lˈɛnɚdz kˈɑːlɪdʒ, bɹˈaɪtən ɡɹˈæmɚ skˈuːl ænd mˈɑːnæʃ jˌuːnɪvˈɜːsᵻɾi wˌɛɹ hiː ɡɹˈædjuːˌeɪɾᵻd wɪð bˈætʃəlɚɹ ʌv ˈɑːɹts ɐmˈɛɹɪkən hˈɪstɚɹi ænd bˈætʃəlɚɹ ʌv lˈɔːz dᵻɡɹˈiːz.
Pickering was born in Melbourne and educated at St Leonard's College, Brighton Grammar School and Monash University where he graduated with Bachelor of Arts (American History) and Bachelor of Laws degrees.