100 Books Like A Guide to the Good Life

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.

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.

Seneca was one of the last of the ancient Stoics who lived during the time of Nero. Towards the end of his life, he wrote several letters to a young prefect, Lucilius. These letters were not just meant to be read by Lucilius but the generations to come as well. Seneca’s letters are well written and cover a wide range of topics as they relate to the art of living. These essays are a ‘how to’ guide to living.

Why this translation? Although there are 124 letters in all, modern translators tend to translate just a selection. Robin Campbell is no exception. I chose this translation because it is as good as any and it is not pricey.

While William Irvine’s book introduced me to Stoic philosophy, Donald took me further into the incredible life of Roman emperor and Stoic Marcus Aurelius. This book takes you deeper into Stoic philosophy. I get asked whom I’d want to have lunch with, dead or alive, and I answer Marcus Aurelius. During his reign he was the most powerful person in the Western hemisphere. History is littered with examples that prove Lord Acton’s quip “Power corrupts; absolutely power corrupts absolutely.” Marcus is a rare exception.

Ryan Holiday, like Steven Pressfield, is a no-nonsense writer whose words inspire you to start that project you’ve been putting off.

Already started it but running into some, well, obstacles? Holiday describes in his book how obstacles are a good thing and inspires us to look for creative solutions. This book made me reframe how I look at challenges, both personally and professionally.

Epictetus is the Stoic who inspired the Roman Emperor Marcus Aurelius. Stoicism is the intellectual origin of cognitive behavioral therapy and a way for leaders to train themselves to focus on the things they can change, rather than breaking their hearts over things over which they have no control. The Enchiridion has the virtue of being much shorter than Aurelius’ Meditations, and contains pithy observations and advice like ‘it is not events that disturb people, it is their judgment concerning them,’ and ‘don’t hope that events will turn out the way you want, welcome events in whichever way they happen: this is the path to peace.’ Leaders need to be good at detachment, and Stoicism can provide valuable tools to help.

Our nation’s most insightful—and readable—sociologist? Boston College’s Juliet Schorr has my vote.

Over the past quarter-century, Schor has probably done more than anyone else in the world to bring grand conceptual constructs like income distribution down to the nitty-gritty of daily life.

Her 1999  best-seller, The Overspent American, strikingly exposes how inequality unleashes a “competitive consumption” dynamic that has us consuming ever more and enjoying life ever less. And that dynamic poses more dangers today than ever before.

As Schor put it in an interview with her I did some years back, we have “no chance” at achieving ecological sustainability “with the kind of extreme income distribution” that we have today. 

Philosophies of simple living are often addressed primarily to the individuals who is seeking happiness. This is largely true, for instance, of both Epicureanism and Stoicism. How Much Is Enough? shows how the questions raised by such philosophies also bear on the economic policies and political culture of rich, modernized societies. The basic argument of the book is that it is foolish for these societies to strive for endless economic growth. They are already wealthy enough to provide the basic conditions of the good life for all their citizens, including a radical reduction in the hours that people need to work. But this isn't happening because capitalism continually inflames people's misguided desire for more stuff and higher status. So the machine just keeps on pointlessly creating desires while plutocrats keep creaming off the wealth of society which could otherwise be distributed more equitably and more rationally. The book offers a… show more.

This is an entirely different kind of book to those listed above. From 1990 to 1996 Amy Dacyczyn, a self-styled "frugal zealot," put out a monthly newsletter, The Tightwad Gazette. It contained all sorts of tips, tricks, strategies, and advice on how to pinch pennies. This book brings all her articles together in a single volume. For anyone committed to living simply–which usually means living cheaply–it is a goldmine. True, not all her recommendations met with my family's approval: mixing real maple syrup 50-50 with fake maple syrup received multiple thumbs down. But browsing through it is great fun, and on almost any page you'll find a salutary reminder of how you could be more frugal. And as we all know, frugality is associated with wisdom and with happiness.

I loved reading about grit–that “passion plus perseverance toward long-term goals” is the key to success–by Angela Duckworth, who pioneered the concept. I particularly loved reading the section in her book, Parenting for Grit, which supports the parenting style of every parent I interviewed who raised entrepreneurial children.

Rather than Permissive Parenting or Authoritarian Parenting, she supports what she calls Wise Parenting, when there’s a “carefully struck balance between affection and respect on the one hand and firmly enforced expectations on the other.”