100 Books Like First You Have to Row a Little Boat

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.

First, let me disclose that I know the author, and that Macleod’s blurb endorsing my writing appears on the back of my third book and a blurb from me shows up on the back of Justice Hill. So, let’s be clear: this is not payback. Justice Hill is simply a great book. It features two everyday heroes; lifelong friends who face conflict. The way they handle their friendship—and their burdens—became, to me at least, lessons in both forgiveness and resilience. Heroes don’t have to save the world; they can save each other.

In this memoir Scott Harrison, founder of Charity: Water, tells of his transformation from a party-seeking youth to a man of grace and influence. Through his charity, he has brought water and hope to millions.

I am deeply inspired by his journey and how he overcame past mistakes to find a new purpose. I knew Scott during my early days in New York City. I support his cause not only because I respect him personally but also because of his approach to philanthropy. Charity: Water applies innovation to a noble cause.

I read this book during the depths of the Covid pandemic. Fitting, indeed, because it postulates a different kind of pandemic, no less terrifying and disruptive. What grabbed me was not the topic per se, though (as prescient as it was, when it was written). Instead, I found myself really cheering for Alexis, a hero who didn’t want the job of being a hero—and yet takes on the challenge while proving that heroes don’t need to be perfect.

I recommend the sequel to Pirsig’s more famous bestseller because I’ve never owned a motorcycle (and I find bicycle maintenance hard enough), but now I own a sailboat—where his second story is set—so when he describes hearing people walking on the cabin roof, or checking the knots on the mooring ropes, I know exactly what he means because I’ve experienced this. Some of his fans felt this sequel was a betrayal of the magical mysticism of undefined Quality he described in the first book. For me, although problematic, it was a necessary clarification and one I not only used for my academic work on a range of controversies from abortion to transgender but also in my life-coaching practice: to inspire holistic transformation on all levels of wellbeing. 

When I read this it felt like a seagoing version of One Hundred Years of Solitude, and it was touch and go which to include in this list. But if you’re like me, and love the sea, there’s no real choice.

In this epic novel we’re shown how the Danish port town of Marstal – and people who call it home – evolve over the course of a century. The novel brilliantly captures the pull that the sea has over the town’s inhabitants, and their struggle to keep what makes them human when faced with its power and scale.

There’s a fantastical element too, just a touch here and there, which somehow matches how most of us experience the unexplainable.  

The first time I read this book I was sailing through the Frisian Islands, where it takes place—though unlike its two main characters, I didn’t have to worry about German patrols or being arrested as a spy. A classic thriller, the remote and shifting islands of the area help to drive the plot. It could, quite simply, take place nowhere else. Great sailing scenes as well!

Bill Tilman was a war hero and an accomplished Himalayan climber – reaching 27,000 feet on Everest without oxygen in 1938 – who turned in later life to sailing as a means of accessing obscure mountain ranges. In 1956 he sailed his Bristol Channel pilot cutter (Mischief) from England to the Chilean channels and made the first successful crossing of the Patagonian ice cap. Tilman was likely not easy to get on with – he tolerates no women on board, and on this particular cruise we never learn the first name of his deputy – but his writing is erudite and amusingly self-deprecating. This narrative concludes with the dry comment: “Ships are all right – it's the men in them.” Tilman sailed to the very end. He disappeared at sea in 1977, in his eightieth year, en route to climb a remote island peak in Antarctica. Would that… show more.

I love this book because it brings two lost souls together for the trip of a lifetime. The heroine, Anna, is an emotional wreck, struggling to move on from the death of her fiance. The hero, Keane, is a steady guy recovering from a major accident. Anna needs a sailing partner for her trip around the Caribbean, and Keane is the perfect man for the job.

I’m a sucker for messy, imperfect heroines like Anna. Trish Doller delivers relatable characters in a charming page-turner of a romance. I love the island-hopping journey, Keane’s Irish accent, and all of Anna’s missteps as she navigates a sea change. 

The Motion of the Ocean has been a longtime favorite sailing memoir of mine, not in the least because I read it during my own sailing years and felt connected to the author.

I appreciate her humorous, honest, conversational, and compelling writing style and love the title of the book, which inspired me to keep adventuring by sailboat and even to write my own memoir.

The narrative focuses on Janna and her husband’s relationship on a small boat in a remote area of the world. It’s a story not unlike mine in regards to relationship idiosyncrasies, the Pacific territory, the couple’s ages, and some of their experiences.

Janna was a teacher in a previous life as well and shares my love for travel and writing. This is an entertaining, well-written book.