The best books inspiring generations of readers to embrace a life of adventurism and escape to realms of avant-garde

Some people are already familiar with the true story of Christopher McCandless, a boy from Alexandria, Virginia who had a seemingly bright future and yet was unfulfilled living in modernity, he chose instead to escape and sought adventure in an unconventional way. 

By abandoning everything from his former life and creating a new persona—the culturally famous Alexander Supertramp.

Unfortunately for Alexander, his story ends tragically after two years when his emaciated corpse was discovered in an abandoned bus in the Alaskan wilderness by hunters.

But his story lives on as an international bestseller that has been translated into 30 languages and continues to attract audiences with his amazing and tragic tale. 

And although ‘Alexander Supertramp’ is still debated today about whether his actions were the result of severe mental illness or a burning desire for transcendentalism, I think that after reading this book readers can agree that it was likely a balance of both.

As for me, his tale was inspirational in a way I had never experienced before because I had always dreamed about what a life experience it would be to disregard modernity and live off the land, traveling by foot or hitchhiking.

It even propelled me to find my own ‘into the wild’ experience and influenced me in ways I cannot credit enough and within mere days after discovering his tale, with only a few hundred dollars, I left home in a similar way and decided that I was going to from this point on—live in my car and find short term work wherever I could and spent years vagabonding across the United States.

For those readers seeking excitement and possibly a push—I cannot recommend Christopher McCandless’ story enough. It changed my life forever.

Some people will argue that of all the movies adapted from books, the book will always win, but in The Curious Case of Benjamin Button, I believe the film adaptation is more alluring than the original short story, but it would not be fair to discredit that this film was influenced by Fitzgerald’s original satire of a child born aging in reverse.

While the movie veers away from the short story in time period, setting and character development, the short story draws more into the philosophical questions I believe we ourselves as a society are subconsciously thinking—even today, nearly a century after it’s writing as to how we contradict the specific wisdom that comes with age while also relinquishing it due to natural mental decline and end up treating our elderly like children.

Unlike the film, the story takes place just after the American Civil War and draws a more satirical and humorous approach to the inevitable aging process which terrifies many of us but helps us see it in a different light.

Both the film and original story inspired me to grip life in a different way, by embracing the humor and tragedy within and transferring its message into my own life if it were a diary of a man who is approaching a time in his life where he may forget everything, and focused mainly about the regrets that may come in the future and encouraged me to take risks in a different way because let’s face it—we will all end up in diapers.

For fans of the film, you must read the story that inspired it, as well as those that read this story for the first time, I highly recommend viewing the film afterwards.

The voice of the Beatnik era lives on through the experiences of On the Road by a young Jack Kerouac who glamorized a culture of a lost and aimless youth to take to the road in search of adventure despite limited financial means and explored the mindset of those that were too young to serve in World War II or remained home in post-war America.

While his story is positively inspiring and thought provoking, I feel that many people have missed a major moral of his story On the Road, and I encourage readers who pick this story up for the first time to heed the words between the lines and understand that this book is inspiring in how it created a new philosophy of life among young people in search of adventure (as well as the hippie movement in the States.) but find a new way to view Kerouac by reading this story as a blueprint of simply ‘what not to do.’

Paul Kemp, a freelance journalist, finds himself in-between a failing newspaper, unethical development schemes, love, lust, and furious Puerto Ricans while exercising the world’s hardest working liver.

Hunter S Thompson delivers a first-person narrative into the American—Caribbean love affair with San Juan, Puerto Rico in the late fifties. Thompson’s words transcend a modern picture by both detailing the lovely landscapes the Caribbean represents and a deeply personal and humorous collection of experiences and events that let the reader analyze each character, including Kemp, for all their flaws as human beings. Thompson’s style of writing has always made me feel a part of this time capsule.

Herman Hesse’s Indian tale follows the ancient journey of Siddhartha, a fictional character on a spiritual path to find meaning in a world full of suffering and greed by renouncing his family and all worldly possessions to become a wandering holy man (Samana).

Along his journey he discovers and meets the actual Buddha (Gautama Buddha), and although he was deeply impressed with the Buddha’s honorable teachings, Siddhartha, disappointed, chose instead to follow his own path believing that one cannot find enlightenment by only following the words of a teacher but instead by experiencing and embracing all aspects of life personally to understand the true nature of enlightenment.

The story itself is captivating because the answers Siddhartha seeks are questions we’ve all asked ourselves, and the answers he discovers help explore the contradictions between the sacred texts of organized religion and the frustrated individual’s approach to find meaning within themselves despite the criticism of other conventional worshippers.

I must refrain from saying much more about this wonderful story because I don’t want to spoil anything, but I’ll conclude that it’s enticing personally for me not just as a novel but more importantly as a guideline to how one must live their life to find true meaning and solace in this strange journey of life and how one may even manifest success while doing so.