In a rapidly shrinking world, a Canadian high school teacher of literature in English reflects on the increasing diversity of her students and the role of technology in bringing to them a sophisticated knowledge of the cultures of the world. In this paper, she describes her experiences from a 20 year journey with using technology in various projects that include teaching students about human agency in global politics, First Nations land issues, the portrayal of the Caribbean in the media, the impact of HIV/AIDS on Africans and the comparison of use of water resources in East Africa and Canada. Through this journey, she comes to the conclusion that technology is an important conduit but the role of the wise teacher, a high quality curriculum that fosters deep knowledge of the cultures of the world, critical literacy and an appreciation of ethics in human agency are vital in bringing about a sympathetic but deep knowledge of the “other” in our midst and increasingly in a rapidly shrinking world where we rub shoulders with all of humanity everyday.