Walden On Wheels: On the Open Road from Debt to Freedom

Ken’s best friend, Josh Pruyn, attended both high school and the first year of college with Ken. Josh is effectively a foil to Ken in the book: Despite sharing some of Ken’s desires to experience the wilderness and become free from debt and normative work life, Josh cannot break free from his bonds of debt for most of the book. Unlike Ken, who left Alfred University after one year, Josh completed his education there, accumulating more than $60,000 in debt. While Josh accompanied Ken to Alaska for brief periods, he generally struggled to find work, finally settling into an admissions job at Westwood College, where his role was to convince other young people to take on large loans.

Josh’s journey is a more relatable example of the struggle of post-undergraduate life; unlike Ken, he moved to a new town, secured a regular job, and struggled to balance his work and social life. When Ken reflects on Josh’s situation working at Westwood College, he notes how Josh fought with his girlfriend, had little time to enjoy himself or his interests, and seemed generally unmotivated and uninspired. Josh eventually realized the unethical role he played in Westwood’s admissions, leading him to testify against Westwood after quitting his job. Josh’s journey was a less extreme version of Ken’s transformation, as Josh slowly realized the value of living freely and according to his ethics and morals. Although Josh was still working to pay off his debt, he was in a better position emotionally and interpersonally than he was at Westwood, illustrating the importance of living a fulfilling life.

As Ken traveled the country, he frequently emailed back and forth with Josh, reflecting the importance of their friendship. While Ken worked to resolve his questions about life and work, he often wondered about Josh and people like him, whom Ken called “loan drones.” As a “loan drone,” Josh was concerned with both having a normal life and paying off his debt, which, for Ken, was an untenable position. Although Josh’s story is less inspiring than Ken’s, both demonstrate how hard work and dedication can resolve the issue of individual debt, while also highlighting the need for broader change in organization and encouragement of young students into large loans and “useless” degrees.

A young woman whom Ken met in Mississippi, Sami had a complicated past involving multiple death by suicide attempts, substance use and abuse, and changing living situations. Sami and Ken began a romantic relationship that lasted after their obligations in Mississippi ended, and they hitchhiked up the East Coast of the US and then to Coldfoot, Alaska. Although Sami wanted to hitchhike on her own, Ken stopped her, noting the increased dangers of hitchhiking alone as a woman, though Ken framed these issues as relating to Sami’s good-natured view of people. When Ken and Sami parted ways, she headed to California to attend community college, and Ken later headed to Duke University in North Carolina.

Sami’s purpose in the book is twofold: She is Ken’s companion and is the only notable woman in the book other than Ken’s mother. As a companion, Sami came up frequently during Ken’s “vandwelling” experiment, as he lamented his isolation and his desire for sexual companionship. However, as a woman, Sami’s presence emphasized the privilege with which Ken approached his lifestyle. Although Ken addressed the issue of Sami hitchhiking alone as a personal one, in which she was too trusting, the reality was that Ken had to acknowledge the difference between his own risk of encountering violence and Sami’s, grounded in the disparity between sexes. For a white male like Ken, the odds of being attacked are relatively low, while Sami—though also white—is a woman, increasing her risk of experiencing many forms of violence. Without the implicit protection that Ken provided, he knew that this risk would likely lead to Sami’s being assaulted, and her presence thus highlights the greater risks that women face in hitchhiking.

A man whom Ken met in Wiseman, Alaska, Jack grew up there, leaving only briefly to attend the University of Alaska at Anchorage, studying biology. After a semester at school, Jack abandoned college and returned to Wiseman, where he grew his own food, had a family, and periodically led tours of Alaska’s wildlife and environment. Ken envied Jack’s lifestyle, noting his closeness with nature, the unbridled freedom of providing for one’s own needs, and the simplicity with which Jack approached his life. Throughout the book, Ken reflects on Jack’s life, noting how Jack lived by transcendentalist thought, keeping himself and his family close to the purity of nature and avoiding the extremes of consumerism and modernity.

Jack’s role in the book, much like those of Josh and other characters Ken met in Alaska, is to show the effectiveness of a simple, frugal lifestyle. Although Jack did not have ready access to a supermarket, a shopping mall, or even consistent utilities except his own generator, he lived a comfortable and happy life in the wilderness. Ken’s envy for Jack contrasts with his disgust at many of the other workers in Coldfoot, whom Ken noted were regularly inebriated, unmotivated, and loud. Jack’s home and life were comparatively quiet and profitable, and Jack worked only infrequently to maintain his life while enjoying the comforts of a well-constructed, reliable home.