Today, postcolonial theorists and activists are urging people to educate themselves on the legacy of colonialism and on different perspectives in the history of Canada. As a white person in Canadian society, I am a beneficiary of colonialism and, as such, I recognize my privileged identity in Canada. Through artistic, academic and writing practices, I pursue personal decolonization objectives. From 1909 to 1947, a community of Compton relatives prospered from unsustainable land-use practices, including operating one of the largest sawmills on Prince Edward Island at the time. Using research-creation methodology, I critically contemplate this family history by creating woven cartographic tapestries of the land my ancestors exploited. Depicting the settler-altered landscape in my tapestries serves to present truths of colonialism in a visual way. Since the arrival of European settlers, dominant land-use practices have favoured profitability over sustainability. As an educator with an environmental and postcolonial perspective, I promote a different kind of relationship with our world, in which economic gain and sustainability are of equal importance. The title “Pedagogy of Discomfort” refers to both the difficult knowledge of colonialism and to the physical demands of making textile art. Despite the discomfort in weaving, I found the process meditative and a time to listen to Indigenous-led audiobooks and podcasts. For me, this fostered a listening practice that helped me better understand the biases and omissions in dominant narratives of Canadian heritage. By considering family history in this context, I am implicating myself in an effort to take responsibility and effect change as an educator.