Ken’s thematic discussions of Living Authentically in a Modern World and Contemporary Transcendentalism and the Power of Nature collide as he describes coming face to face with a grizzly bear, recalling his recurring dream. He notes how he recognized “the animals, the waters, the mountains” in the grizzly bear’s eyes, calling them the “wild green eye of nature” (267). For Ken, the bear was a single entity encapsulating both the beauty and the danger of nature. He notes that he always “kept [his] gaze averted” from the eye of nature, but “now [he] was left without an option” (267). Ken reveals that much like his forays into poverty, his forays into nature were inauthentic explorations into the unknown with the safety net of society only miles away. Ken speculates that he dreamed of the grizzly bear because it is everything he wants to be—“wild, strong, free” (268)—but he also realizes that he can never attain the freedom and wilderness that the bear represents for him. The encounter with the bear was a moment when Ken “was afforded a glimpse of [his] true nature” (272), but that nature includes the civilization from which he comes to the wilderness. Despite all his efforts, he acknowledges that he can never fully shed the veneer of socialization that keeps him from becoming part of the wilderness.

Critically, Whitney reminded Ken about “the wolves, the calf mortality rate, the -60°F winters, and the legions of bugs that try to eat the caribou alive” (271), grounding Ken’s fantasies of nature in a harsh reality. Although Ken says, “Give me a full life over a long one” (271), his position is reminiscent of Thoreau, who Ken acknowledges was never truly isolated or entrenched in nature. From Ken’s position of relative safety, nature remains an adventure to entertain for periods of time, without the comparative dangers of long-term exposure or abandonment. However, like Thoreau’s experiment, Ken realizes that his own experiment “wasn’t just for him. It was for everyone” (279), essentially justifying the book to invite readers into his adventures and demonstrating a different way to live and explore.

In describing how Josh testified against the predatory practices of Westwood College and how Ken gave his graduation speech, the book resolves the theme of Debt as a Necessary Burden. Josh, inspired by Hannah Arendt’s Eichmann in Jerusalem, realized that everyone is complicit in the system of student debt, which normalizes and encourages young people to take out exorbitant loans for their education. His testimony condemning these practices expands beyond Westwood College to the heart of American perspectives on debt, in which people view debt as a necessary step in achieving success. Nonetheless, Josh realized that “even though his education cost him tens of thousands of dollars and years of work, it was worth every goddamned penny” (276) because it allowed him to see the ills of society and step forward to criticize them.

Ken, however, presents an opposing perspective on debt, as he succeeded in completing his graduate program without debt: “Today, students struggle to fly past a poor job market, around unpaid internships, and through the sticky web of student debt that is nearly as wide as the sky itself” (294). Ken frames debt as a burden and expands his understanding of why debt is necessary for these students. However, Ken’s main point regarding debt is the need for a “frontier,” a way for students to expand their minds instead of their wallets by exploring themselves and the world around them. In considering debt as a necessary burden, Ken points to the “real villains who need vanquishing, corrupt institutions that need toppling, and the great American debtors’ prison to break out of” (296) as the new frontiers on which young students can pave a new path for themselves.