100 Books Like The Second Mountain

Kidder’s book follows the lives of a group of brilliant, funny, and maniacally driven entrepreneurs as they race to get their new minicomputer, the “Data General Eclipse MV/8000,” to market.

The technology is totally obsolete – who under the age of 40 has heard of a minicomputer? – but the story is somehow timeless. The book won the Pulitzer and is still a fun and riveting tale of what it takes to get a product to market on an ever-changing technological frontier.

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 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.

I love this book because it gave me a roadmap for navigating the conversations I used to dread, many of which involve ethics.

As a supervisor and leader, I’ve faced moments where my voice was shaky, my palms were sweaty (think “Mom’s spaghetti”), and my brain was frantically trying to script the “perfect” thing to say. Crucial Conversations reminded me that it’s not about perfect—it’s about being present, showing up, and having the conversation even when it is difficult.

This book highlights the importance of inviting different perspectives into tricky conversations. I’ve used its tools to prepare for and navigate tricky conversations in a collaborative way, focused on shared goals, mutual respect, and safety—even when emotions run high. It’s my “conversation courage” handbook.

I must have read a hundred books about story structure over the years. Somehow, perhaps because of some story-related blind spot on my part, none of them ever seemed to stick.

My problem was always the middle. Middles can sag. It seems that a story's interior becomes little more than the wasteland a protagonist must traverse to get from the mystery of a beginning to the ultimate challenge of an ending.

Yorke's Into The Woods celebrates the middle. He reminds us that the essential crux of a story lies in its midpoint. Right at the heart of an effective story, he argues, lies a fundamental transformation, a change so great that the protagonist emerges with new powers into a new world.

Furthermore, by analysing stories in five acts rather than three, he allows for an elegant symmetry in which the first and fifth, second, and fourth acts mirror one another.… show more.

I could have chosen any Raymond Chandler novel for this list; he is such a brilliant stylist, one of the best in the language.

His lugubrious, heavy-drinking, first-person detective Philip Marlowe is my kind of fictional hero, a genre-defining character, perpetually alone though he yearns for the glamorous women he meets.

Richard Barrett’s book is like the engineer's guide to self-enlightenment. Like David Brooks in the second mountain, the author describes a personal journey to discover one’s inner purpose and soul.

The book's first section explores ways to develop self-knowledge, even providing a variety of charts to explain the author's philosophical concepts: exploring consciousness, self-identity, and beliefs. Part two defines ways to discover one’s purpose and then articulates pathways and strategies to live that purpose.

Had I read and studied this book in my early life, my path might have been much different. That is, of course, if I had the mind to follow Barrett’s suggestions.

This book, the transcript of Thomas J Watson Jr.'s 1963 lecture at Columbia University, describes the core values on which the IBM corporation was built: respect for the individual, best customer service of any company in the world, excellence in everything we do. The small book is rich with guidelines for good management and examples of real-life incidents where the principles were applied.

Watson's book is fundamentally important today because it provides a foundation for understanding how IBM, the company for which I invested much of my career, lost its way when it deviated from Watson‘s core values.

Martin Cruz Smith’s first book in his Arkady Renko series, Gorky Park, did very well and was made into a successful film. Later books are perhaps not so well known which I think is a great pity. Smith’s books ooze atmosphere, intrigue, and authenticity taking us into other worlds—in this case, that of Russian oligarchs and the deadly exclusion zone round Chernobyl. Arkady Renko is an incorruptible investigator in a society where everyone is on the make—another parallel I’ve found very applicable to my own work. And, unlike many thriller authors, Smith is also a brilliant writer of scintillating, gripping narrative. I’d love David Hidalgo and Arkady Renko to meet and have a chat over a few glasses of red wine, vodka, or both!

I could easily recommend any of Robert Harris’s “intelligent thrillers” however I’ve picked this one because I like the idea of an “ordinary” man who finds himself in the midst of a dangerous mystery. Briefly, The Second Sleep is set in the future after our civilisation has destroyed itself and where life is now functioning at the medieval level. The church, which controls everything, has banned investigation into the past. A humble priest is sent to visit a village in his parish and begins to suspect that things are not as they seem. Eventually, against the orders of the church, he decides to try to penetrate the past with alarming consequences. So, as for my character, David Hidalgo, we find that ordinary people can make a difference!