The best books for making the most meaningful life

Zen came out when I was a teenager, when it took the world by storm. It still holds up as a compelling story of an independent-thinking father and his son taking a cross-country motorcycle trip and as “an inquiry into values,” as Pirsig subtitles the book. This book contains multitudes. It makes you think about the nature of genius and mental illness while making you ask yourself, “what is quality?” and how does our consideration of quality affect the meaning of our personal lives. Reading this book helps us see how much we are shaped by our culture and how important it is for us to articulate our own philosophy of life.

Reading This is Water is a heartbreaking but beautiful experience, because the author, a philosophical and literary giant, took his own life. Wallace gave us so much in his too-short life. And, he had so much more to give. Nevertheless, this tender little book will fill you with compassion for yourself and for humanity in general. It is not a manual for living, but for seeing the world around you more clearly so that you can let more beauty and goodwill into your mind and heart while spreading the same to others. This is a little treasure.

I cannot count the number of times I’ve read this book. You will no doubt see it listed as a favorite on many book lists because it is a masterpiece and because it is searingly true. Viktor Frankl was a psychiatrist who spent several years in Nazi prisons only to learn that almost his entire family had been killed. His legacy is not only his personal example of the joyful and useful way he lived his life after liberation, but his conclusion that meaning is more important than anything for living the best possible life. Meaning trumps happiness, comfort, and wealth. This book compellingly shows how we make life meaningful for ourselves and for all whom we love.

I keep this book on my nightstand because it helps me bust through my creative blocks every time. The opposite of depression is expression. It follows that living a meaningful life is predicated on organized and artful expression. But everyone knows that so much gets in the way of that expression. Professionals and amateurs both are afflicted by creative blocks. Pressfield helps us identify the work we feel called to do and shows us how to do an end-run around all the forms that our resistance may take.

I have carried The Universal Traveller with me for decades and it sits next to my desk in my office. Any time I get jammed about next steps to take toward a worthy goal, I dip into this quirky, useful book. The authors look at life and all our efforts to live it with dignity and value through the lens of design and problem solving, by which they mean “making dreams come true.” The most meaningful life is one lived with a stoked imagination and the willingness to try on new ideas and methods. The UT is quaint because it was written before we were all digitally connected, but its wisdom stands the test of time.