This thesis-project equivalent documents an autoethnographic study that leads to the design and development of a curriculum. The autoethnography documents lived experiences in Guadeloupe, a French Antillean island, during the 2016-2017 academic year. Concepts of identity including race and belonging were subjectively explored in the autoethnography and then through activities in the curriculum. The curriculum was designed to address the specific cultural and academic needs of high school students in Guadeloupe. This English as a foreign language environment emphasized multiple languages as a source of success while battling its own history of cultural genocide. A balance of embracing diversity and maintaining traditional cultures has been an ongoing struggle for foreign teachers working within these diverse populations. The curriculum presented in this paper addressed the complexities of that setting while fostering a space for young people to discuss their own perceptions of identity and exploring them through Tumblr. Enforcing digital etiquette practices, online security and privacy policies, and navigating the digital world in English were tangible tools developed through the program. The program emphasized both soft and hard skills specifically designed for a Web 2.0 era where young people are expected to be well versed in technology and critical analysis.