To better understand how young Alaska Native (Inupiaq) people are creatively responding to the tensions of growing up in a world markedly different from that of their parents and grandparents, the pilot study examined youth-produced digital stories as representations of their everyday lives, values, and identities. Two hundred and seventy-one youth–produced digital stories were examined and assigned descriptive attributes; of these, 31 stories were selected and subjected to a more rigorous coding and a thematic analysis. Findings fall into three main categories: self-representation, sites of achievement, and relationships. Participants’ digital stories overwhelmingly depicted positive self-images that included both codified cultural values and pop cultural images to construct novel forms of cultural identity. The gendered depictions of achievement signal a need for more varied, valued, and accessible avenues for success for boys. Lastly, relationships were prominent in the stories, but there was an absence of young adult role models, particularly men, in the stories.