100 Books Like Working

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.

The gold standard of rock and roll oral histories. Two authors, years and years in the making, chronicling one of music's most incendiary eras. "Will you die for the music?" Lou Reed asks in the early pages. In other words, how many knife fights, sleepless nights, and dead friends would it take to stop you from chasing artistic salvation?

Reading this book while I wrote my own made me realize just how sterilized my scene (like much of America) had gotten by the turn of the millennium. Third-wave emo wasn't famously dangerous or gritty, but many of its icons grappled with life-threatening addiction and mental health issues (even more than I expected going in). Yet, thankfully, almost all of those band members are still with us. Please Kill Me illuminated this. It's no accident the final word in my book is "survive."

Hochschild is a sociologist, exploring modern types of jobs that commercialize human emotions. Think of flight attendants or bill collectors: people who have to smile at clients or remain polite, even if these clients make that very hard. Hochschild shows the impact of such acting; I use her insights in my work on sex work.

The quintessential book for anyone writing a modern biography, as well as a page-turning read. Jean Stein and George Plimpton brilliantly create a moving portrait of an Andy Warhol acolyte who became a Warhol Superstar and then an enduring icon of the 1960s, before dying of a drug overdose at age 28. A fascinating oral history that simultaneously depicts a beautiful, glamourous, and troubled young woman and a nation undergoing a paradigm shift.

This is the definitive look at an American comedy institution (yes, we know it kinda sucks now) and includes input from almost all the show’s biggest names. The book features the requisite amount of sex, drugs, and rock and roll — plus fisticuffs and lots and lots of backbiting — but it also has some surprisingly tender moments, like Bill Murray’s recollection of the last time he saw his castmate, Gilda Radner, before her death.

Dazed and Confused, Richard Linklater’s plot-light, pot-heavy 1993 film about Texas teens hanging out on the last day of school in 1976, is perhaps my favorite movie ever, so I was already inclined to love this oral history about the film’s creation and legacy. Maerz expertly weaves the voices of almost everyone involved in the project — from breakout star Matthew McConaughey to members of the crew — to create a highly entertaining, super-compelling look at a stoner cinema classic.

I read this book when it was first published when working low-wage ‘regular’ jobs was something I feared. I had been poor for so long and worked low-wage regular jobs before and through 9 years of college and after until I became an escort. As much as being an escort was shamed, it was nothing compared to the shame of not being able to survive with two low-wage jobs that eat up all your time, your choices, and your health. Then here was this powerful, insightful book.

The author is a journalist who goes underground, takes these jobs, and tries to survive. What is revealed are the lives of so much of the population in America that are working this way. I read this book in one day. Once you see it and have felt it, it’s impossible not to see it and want better for all of us.

Nothing much seems to happen in this remarkable novella, which describes a single lunch break of a man at work.

Actually, though, the reader gets to eavesdrop on the man’s ruminations about everyday things—shoelaces, bathroom blow dryers, vending machines, office supplies, and so much more.

These ruminations are practically Proustian; they start with something ordinary (a milk carton), followed by a digression (memories of having milk delivered to his home), interrupted by another digression (about his sister’s milk allergy), and veering into philosophical territory (pondering the nature of all childhood memories).

Reading this novella is both exhausting and exhilarating. It’s like wandering haphazardly through a maze of ideas and memories. Luckily, the novella is short enough that the reader never grows bored or tired.

One early summer afternoon, the body of a young woman is dredged from the mud of Lake Vättern, and Detective Inspector Martin Beck of the Swedish National Police is assigned to the case. Who was she? Who killed her? These questions remain unanswered for months and months (and months). Catching a killer, it seems, is a slog, and the routines of police work are captured here in all their tedium. And this is exactly why I love this book, as it compellingly dramatizes (to quote from Henning Mankell’s introduction) “the fundamental virtue of the police: patience.” There’s a heroism to these steadfast and rumpled men, and something thrilling about their dogged, often frustrating, yet ultimately successful pursuit of the truth.

During Italy’s post-WWII economic boom of the ‘50s, in an anonymous northern Italian city, an unskilled laborer named Marcovaldo struggles to support his wife and five children (or seven, or four—the number changes). In twenty tightly-plotted tales, we observe him stealing a trout, stealing a rabbit, getting lost in the fog, shoveling sidewalks, trying to fall asleep, trying to stay warm in the winter. Each “adventure” complicates absurdly, and some are more dire than others. Though on the brink of poverty, Marcovaldo hangs on, strives and fails, and strives anew, never losing his naive sense that things will turn out fine. The best comic writing is always tinged with the tragic, making you laugh and making you feel, and Calvino is a master.