I’m jumping right in today for this longer edition. These are two books that have the power to change your life. Also included is a really fun philosophy-laced interview with Kyle Eschenroeder.

When Breath Becomes Air by Paul Kalanithi

Published: 2016 | Pages: 225

“Even if I’m dying, until I actually die, I am still living.” —Paul Kalanithi

In the midst of any big life-changing event, it’s only natural to think about meaning. What is this all about? What are we here for? What’s the best use of our limited time and attention on this planet?

I initially read When Breath Becomes Air after the birth of my first son, back in the summer of 2015. While rocking him in the middle of the night, settled into our hand-me-down glider, I flipped the pages on my phone, astounded at the beauty and honesty and depth of feeling this memoir produced. I say this with no hyperbole: the late Paul Kalanithi spoke to me in those late nights and helped me become a better parent.

So when my daughter was born in early 2018, I read it again. The second reading was just as impactful and reinforced those passages and ideas that so moved me the first time.

In the months leading up to the birth of third child, I knew I’d be reading When Breath Becomes Air again once he was born. This go-round was perhaps the most profound. I realized that Paul’s words had become embedded into my psyche so deeply that, upon reading them again, my soul answered with an affirmative, “Yes, that’s how it is!” rather than with the more eye-opening realization of a new revelation.

Books—in concert with a life lived—can change you. This is a book that has changed me, to the core, for the better.

Dr. Paul Kalanithi was not at the pinnacle of his career, but he was just starting up the curve that would ultimately lead to that apex. In his late thirties, he was a well-known neurosurgeon-neuroscientist with a knack for philosophy and literature too. The first half of the book details the hard work—almost indescribably hard—of that rise.

That first part is beautiful, no doubt, and I could spill plenty of electronic ink detailing how it moved me. But it’s the second half of the book that brought me to tears all three times I read it.

Right when everything was clicking in Paul’s life, he was broadsided with a cancer diagnosis—a bad one—that was a supremely bad stroke of luck for a man of his age. Along with his wife Lucy, Paul embarked on a journey to figure out what really makes life meaningful. He sought that meaning with everything left in his tank and then pursued it once he found some answers that seemed right (because is there really a final answer to that ultimate question?):

“‘Will having a newborn distract from the time we have together?’ she asked. ‘Don't you think saying goodbye to your child will make your death more painful?’

‘Wouldn't it be great if it did?’ I said. Lucy and I both felt that life wasn't about avoiding suffering.”

It’s nearly impossible to answer the question “Do you have a favorite book?” If I were ever forced to answer, though, I wouldn’t hesitate to name When Breath Becomes Air. You won’t be the same after reading it.

Related books I’ve read/reviewed: The Death of Ivan Ilyich by Leo Tolstoy (read my review), The Midnight Library by Matt Haig (read my review), Cutting for Stone by Abraham Verghese, Without Explanation by Rod Jasmer

Books added to my reading list: Being Mortal by Atul Gawande, The Bright Hour by Nina Riggs, How We Die by Sherwin Nuland

Quick premium member update: This week I sent premium subscribers another edition of The List, in which I dished out a few recommendations for great books about a few of our low-ranked presidents. Check out that list, and all the premium archives, by subscribing below for just $5/month:

Subscribe now

The first month is always free. Do you have questions about being a premium member? Check out the benefits here, or email me back. I’m happy to answer your questions.

On Caring by Milton Mayeroff

Published: 1971 | Pages: 110

“Through caring for certain others, by serving them through caring, a man lives the meaning of his own life. . . . he is at home not through dominating, or explaining, or appreciating, but through caring and being cared for.”

This is a delightful book that serendipitously found its way to my shelf through the writing of my friend Kyle Eschenroeder (see below). It’s a small work, penned 50 years ago, that Kyle has quoted in a few impactful articles and those passages always stood out to me. I finally bought it, read it in about two days, and experienced a true paradigm shift in the process.

The gist is pretty simple: the act of caring for others can constitute the meaning of your life. It’s quite a moving message when the interpersonal roles of your existence are considered. Meaning, we tend to think, most often comes from our work. But if we’re intentional about it, we can find the same fulfillment and satisfaction in our roles as parent, child, friend, neighbor, and sibling.

Caring is not easy, that’s for damn sure. But when love enters the picture, what was once an arduous task becomes an act that we can inexplicably take joy in:

“Obligations that derive from devotion are a constituent element in caring, and I do not experience them as forced on me or as necessary evils; there is a convergence between what I feel I am supposed to do and what I want to do. The father who goes for the doctor in the middle of the night for his sick child does not experience this as a burden; he is simply caring for the child.”

Mayeroff describes the various aspects of caring, as well as what caring feels like. It’s partially philosophical (some of those bits went over my head) and partially a guidebook for how to care for someone, or, at times, something. It’s utterly unlike anything I’ve read before.

I won’t say more than that for now—On Caring is not a book that begs for a long review, other than to say that your idea of what brings life meaning may fundamentally shift after reading it. As I was reminded of in Kalanithi’s memoir too, life’s greatest gifts are always found outside the self.

A Few Bookish Questions With Kyle Eschenroeder

Kyle is one of the most thoughtful writers I’ve come across on the internet. His articles on Art of Manliness are some of my favorites that we’ve ever published, and his Pocket Guide to Action is a book I turn to on nearly a daily basis. His newsletter is required reading too. He was generous enough to provide some amazing book recs below.

1. You're a marketer/entrepreneurship guy with the soul of a philosopher. How did you get that philosophizing streak? Were there books that initially pushed you in that direction?

As long as I can remember, I’ve been pretty focused on living life as well as I possibly could. I was pretty certain about what that meant until later in college when my parents got divorced, I shut down a couple big projects, and I experienced a prolonged, deep depression. At that point I realized that maybe I didn’t know exactly what it meant to live a good life, and so I started looking wherever I could find answers (or helpful questions).

Book-wise, things got weirder as I needed more from philosophy. Basic self-help stuff was motivating early on, but weren’t great in helping my depressed mind that needed something more . . . sincere? Trustworthy? I remember reading Nietzsche’s Beyond Good and Evil on a backpacking trip with my sister and it turning my world upside down. That book helped me realize how fundamentally a book can change a person.

2. It seems like much of what you read is in the non-fic/business realm. Do you read much fiction? Any favorites?

Novels definitely get less of my time than they should. Each time I finish a great one I know that it’s going to be more useful than any nonfiction book. Stories or examples from novels are more likely to pop up for me when I need them than non-fiction books. And I think you can’t actually know what great writing is unless you spend time with novels. The bar is just so much higher.

A few of my favorites:

—Most things by Neal Stephenson, but I like his early shorter books like Snowcrash and The Diamond Age a lot.

—Zorba the Greek was incredibly fun to read. It mixes philosophy with a story, which I love. The interplay of the serious guy and the wild man are really fun. The section about the “frugal heart” is an example of an idea that you could read in a philosophy book, but there’s no way it’d sink in like it does when you read the book.

—Asimov’s Foundations trilogy is absolutely incredible. The world building, exploration of religion and power, and geopolitics over vast periods of time is mind blowing.

—So is the Dune saga.

—Fredrik Backman’s A Man Called Ove was really touching, and his new book Anxious People is hilarious and touching.

—Private Citizens does a great job at painting a picture of a certain group of millennials.

—Sheila Heti’s How Should a Person Be? is super innovative and fun to read. It’s pretty autobiographical and is great for any artsy people (I do think women would particularly like it).

—Thus Spoke Zarathustra is one of the only novels I’ve reread. Nietzsche is just intoxicating if you’re in a place to appreciate it.

3. Are there authors or books that have particularly influenced your approach to writing?

Definitely more than I know. Steven Pressfield’s The War of Art made me believe a short book with half-page chapters could work, which allowed The Pocket Guide To Action to exist. You actually pointed out that a lot of my stuff is in a similar style to Maria Popova, which I didn’t recognize until you said it and now it just seems pretty obvious.

I think different authors have freed me to do what was available to me at different times. I remember reading a F. Scott Fitzgerald quote about how, when you’re young, you don’t have real skill, so you have to rely on energy and emotions. That made me get much more “vulnerable” rather than trying to write well, which I think helped me avoid trying to be an expert. Jack Kerouac talked a lot about writing reality as plainly and directly as possible, which was helpful. He also gave me this line “respect your experience” which is helpful when you feel your point of view isn’t valid. Anne Lamott’s Bird By Bird was just this wonderful reminder to get it done.

There are hundreds of these little tidbits that gave me the permission I needed at the time.

4. Have any favorite or especially influential business/entrepreneurship books you recommend?

I’m trying to think of ones that aren't super common:

—The Fish That Ate the Whale is just an amazing business story. This guy went from selling old bananas to taking over governments.

—Taleb’s stuff is so good. I think Fooled By Randomnessgets overlooked because it was his first non-textbook book, but it’s worth going back to.

—Titan is an incredible biography of John D. Rockefeller.

—Obliquity by John Kay does a great job showing how some things aren't always most effectively achieved by aiming directly at them.

—The Anatomy of Humbug is the marketing book I wish everyone would read. It gives an invaluable, brief history of marketing and the various lenses that come and go with different trends. I don't know of a better tool to frame the hype from new marketing consultants that come in spouting the death of this or that or some new paradigm.

—Alchemy by Rory Sutherland is a call to arms against our obsession with spreadsheets. Nobody describes how psychological value is created as well as him. It's also just super entertaining.

—Specific books, courses, newsletters, and communities. Books are great, but I think for a lot of niche business stuff, most people will find more quality information by taking online courses, joining paid communities, seeking out newsletters, and reading bad-looking (and probably poorly written) books about the very specific niche thing you're interested in.

5. Are there books you find yourself referencing, thinking about, and/or recommending over and over again? Basically, do you have any all-time favorites that have shaped your life and your thinking?

—On Caring has been the book I've returned to and gifted the most since I discovered it five years ago. It's short and has valuable insights to apply in literally every realm of your life.

—I think about Taleb's Antifragile all the time, especially when I see parts of my life becoming fragile.

—I think of Pressfield's The War of Art all the time when I find myself playing small; his description of "The Resistance" can be really helpful.

—Emerson's essay “Self-Reliance” comes to mind often when I find myself losing touch with who I am. This is why I wrote The Guide To Self-Reliance.

—Roman Honor was recommended to me by Brett, it's a somewhat obscure history book and is absolutely intoxicating. The book intimately introduces the reader to how people in a different time and place processed the world. It's a book that shows clearly that how our culture is created determines the possibilities of our inner lives. Fans of Stoicism especially should read it. The Art of Manliness article "Stoic Philosophy - Does It Extinguish The Fire Of Life?" is a great introduction to some of the ideas.

—The Passion of the Western Mind tells the story of Western thought. Like Roman Honor, it shows how differently humans can experience life depending on the philosophy they're operating under. I love books like this that show not primarily the history of events, but the history of human perspectives—it makes you realize how deeply your perspective of the world is determined by your place in history.

—John Kaag's three books on how a philosophy worked on/through him (Hiking With Nietzsche, American Philosophy, and Sick Souls, Healthy Minds). In fairly short, quick-paced books he gives an incredible introduction to and history of a philosophy, biography of a philosopher, and memoir of how the philosophy worked on him. It's amazing. I don't know how he does it.

6. What are you reading and enjoying right now? What’s next on your list?

I'm currently reading:

—Feeding Your Demons is maybe the most practical book I've seen about dealing with one's shadow (at least parts of it). It introduces a simple meditation technique which has been really effective for me so far (and also feels totally ridiculous at certain points).

—Leisure: The Basis of Culture is a short essay written in Germany post-WW2. This book is dense with insights about just how deeply our obsession with work and effort as humans go, and how widely these impact us as individuals and as a society.

—The Stoic Challenge is a fairly short book based on a simple philosophical tool: Pretend that every obstacle you encounter was placed there by the Stoic gods as a way to test and improve your tranquility. I read this just before visiting a family member in the ICU, so quickly discovered it's limits. Still, it's one of the more practical Stoic books out there and I really enjoyed it.

—How To Decide by Annie Duke is a workbook using her decision making framework. It's been helpful with a couple big decisions coming up for me.

Thanks for the time and inbox space, as always. I’d love to hear what you’re reading, too! If you enjoy the newsletter, I hope you’ll consider subscribing as a premium member:

Subscribe now

Share What to Read Next

It does a lot to support what I’m doing here. Have a great weekend everyone!

-Jeremy

Read More Books

What to Read Next (No. 162): nothing less…