100 Books Like Zen and the Art of Motorcycle Maintenance

A timeless meditation on purpose, suffering, and the human spirit. While not about entrepreneurship, this book is essential for anyone seeking to understand the deeper meaning behind their work. Frankl’s insight—that we can find meaning even in suffering—is profoundly relevant for founders navigating hardship and uncertainty. 

What struck me most about it was how Frankl captured the Holocaust not just as a historical event, but as a raw, existential landscape. I’ve seen many films and documentaries about that era, but Frankl’s account stands apart. His lens is philosophical, not just historical. His insight that meaning, not pleasure or power, is the primary driver of human life resonated deeply.

I've focused on the idea myself that many entrepreneurs pursue ventures not for wealth or control, but as a way to fill a deeper existential hole. Frankl’s writing felt honest, profound, and necessary. This is a serious and enduring book I’ll return… show more.

This book appealed to our spirit as travelers and explorers.

We read it after a trip to Ushuaia, Argentina—close to where the story of Endurance unfolded. We found in this story the essence of what it means to be human—to take on big, hairy problems, to expect the unexpected, and to survive against impossible odds.

What stayed with us is how human character is revealed in the most adverse situations, and how, when we are faced with life and death, nothing is truly right or wrong, only choices that must be made to survive.

Sometimes, I need reminding that the greatest discoveries can be close at hand and that simply living alertly is a sublime source of joy. When I read this book, which I have done again and again, I feel my perceptions sharpen, my sense of humor renew, and my hunger, both to read and to write, begin to stir.

As youth is sometimes wasted on the young, so is this book, which is too often assigned to people who aren’t ready for it. Thoreau’s mind is like a fire I never tire of sitting beside. He’s a rebel, a curmudgeon, a jokester, a poet, and the most down-to-earth philosopher our culture has seen. And he knows that wonder is a breakfast food, which he dishes out with utter nonchalance.

A multi-day walking trip requires a page-turning thriller. It is one of the most intriguing mysteries I’ve ever read. It dragged me into another world and then deeper into a story within a story. Lying in uncomfortable beds in noisy hostels while backpacking in Australia, I was beguiled and forgot my own reality.

Years later, this book stayed with me and influenced my debut novel despite, I think, never really understanding it. However, writing this review has made me start reading it again. I’m already baffled, but I'm hooked!

This book hit me as both tragic and strangely hopeful.

Chris McCandless walked into the Alaskan wilderness with little more than a backpack and a stubborn streak, and people have argued ever since: was he brave, reckless, or just plain stupid? But his compulsion isn’t as rare as we might think. In my book, Cole feels the same tug—escape the sterile shoebox apartment and the $8 lattes. This can’t be all there is.

What drew me in wasn’t the verdict but his hunger for something real—stripping away every layer of artifice most of us cling to. Krakauer tells it with empathy and curiosity, letting you wrestle with the questions instead of handing you neatly typed answers. I recommend it because it forces you to stare down your own compromises: freedom versus responsibility, idealism versus pragmatism.

Admire Chris or dismiss him, you won’t forget him. And the story lingers like a… show more.

I adore this book because it is so unique—I’ve never read anything quite this specific or niche which seems so all-encompassing.

It is the story of a life lost, and a life found. Of a father that dies and how the recovery of his daughter is tied up with the start of a new relationship—with a goshawk.

At the outset, the author is so wonderfully eloquent on all aspects of loss; the sudden jarring sense of confusion when a person dies and you have their possessions still in your hands; the struggle to keep in touch with reality (“for weeks I felt like I was made of dully burning metal”); the desperation to see the back of grief when new relationships are desperately grasped at, and fail of course, because of that desperation. 

The goshawk saves her (and us) from the darkness, as she becomes gripped with the… show more.

A deserved, all-time classic, this book seems to transcend time to capture the spirit of wanderlust. I was young and impressionable when I read it for the first time, and it inspired a sense of profound restlessness to explore, grow, and hit the road to see for myself. 

Neal Cassidy and Jack Kerouac are wild, occasionally unhinged protagonists, and their journey consists of hustling, romance, and drinking their way to a good time. Kerouac’s writing made me long for similar misadventures, where life is simple and finding the road is all that matters. Subversively, the novel promotes a full life and whole human experience, which makes working 9 to 5 that much more difficult.

This is classic literature in the realm of American travel.

I had no idea that “blue highways” existed, and even though Heat-Moon went cross-country back in the 1970s in his van equipped with his igloo cooler and makeshift bed (not like the $100k fancy campers you find today), the type of people you meet and experiences you have in this amazing country are still relevant today.

In Blue Highways Revisited, I was shocked to read how long it took for this book to get published and the stacks of printed-out drafts he had of it (I think it was like four feet high). If there are any travel writing classes taught as part of a creative writing program, then Blue Highways better be on the list. 

This classic is my go-to for the challenges of living the creative life and how to push through them.

In short, punchy chapters, it identifies the main source of blocks writers and artists have and how to push through them.

I love its approach to the workmanlike attitude one needs to have to create consistently and move toward a goal, and how to be clear-eyed about the inner “resistence” we all have that seems to want to stop us.

Well-known American author Jack London experienced a genuine decline into vagrancy in the US during the late nineteenth century.

In his 1907 memoir, he depicts the realities of the vagrant’s life without flinching. The detailed descriptions of begging for sustenance from strangers’ homes, risking death to evade detection on fright trains, and the life of inmates in the state penitentiary are as gripping as they are appalling.

The only US book in this collection of recommendations, The Road confirms very similar experiences and challenges facing the homeless on both sides of the Atlantic.