Writings That Changed My Life

Here are some articles and books which have influenced me greatly

It’s hard to attribute all our thoughts back to the origins from whence they first came, but below are some readings that shaped the way I see the world. It’s impossible to order these in a way that doesn’t give too much prominence to some and not enough to others, so I’ve put things in a semi-random order by category.

Other than Man’s Search for Meaning, none of these books fall in today’s list. These are instead ChatGPT’s take on “A cartoony image representing the books that changed a person’s life.”

Life as a Whole

• Four Thousand Weeks, by Oliver Burkeman. A reminder of how precious little time we have, and the importance of treating every single week as a substantial block of our entire lives.

• In a similar vein, Tim Urban’s The End of Life was a revelation on how little time we have with our parents. By the time you leave home, you will have spent more than 90% of the time you’ll ever spend with your parents even if you visit them 10 days a year. Two years ago, I moved my parents from Maryland to our home in Seattle when my mom was diagnosed with advanced liver cancer. It was invaluable to spend those final 9 months of her life in person with her.

• The Practicing Stoic by Ward Farnsworth. This makes the otherwise disorganized work of famous Stoics like Seneca, Epictetus, and Marcus Aurelius readable. Focus on what is within your control. What is said isn’t itself offensive; your choice to be offended turns it into an offense. Was your broken leg a travesty, or perhaps the lucky happenstance that saved you from subsequent devastating loss? By realizing our responses to events dictate our experience of life, we turn almost everything around us into something within our control. I’ve read this book multiple times in my life and find it profoundly helpful each time.

• Meditations by Marcus Aurelius is one of the classic Stoics texts, straight from the horse’s mouth. These diaries were were published posthumously without its author ever meaning for them to be read by the public. Knowing this makes it even more remarkable how wise an emperor Marcus Aurelius was. The book makes concrete the daily struggles of living well, and reminds us how people even thousands of years ago were pretty much the same as today.

• Man’s Search for Meaning, by Viktor Frankl. Freud, with nothing but untested philosophical principle, claimed he could predict the behavior of any man by first reducing him to starvation. Frankl, having lived through a WWII concentration camp, proffers empiric evidence that people behave very differently from each other — even when starved equally near to death — based on their individual sense of morality. This book is a reminder of the depth of human suffering as well as the existential importance of hope as a motivator of our lives. Frankl feels that asking the meaning of life while in the midst of living it is like asking the meaning of a movie in the middle of watching it. We can only truly say what the meaning of any life is once we see the entirety of its arc.

• I used to recommend Delivering Happiness (by Tony Hsieh) as a guide on how the interests of employees, shareholders, and customers can all be satisfied if we see the world as positive-sum. Given Hsieh’s subsequent apparent suicide after years of struggling with drug addiction, I’m now more likely than not to instead share Jewel’s letter pleading with Hsieh to, in a way, save his own soul. Delivering Happiness is nowadays a reminder to me that there’s a vast canyon between understanding what’s good for our lives and living it.

Systems Thinking

• Meditations on Moloch, by Scott Alexander, for which this Substack is named. Everything is determined by systems — which, if you understand them, predestine outcomes. Everyone can live in a little house in the neighborhood if only one parent works. Once a few families start earning dual incomes, the price of housing will quickly require both parents of all families in that neighborhood to work in order to live in those exact same houses. If you bail out banks each time they fail, you should not be surprised when they take increasingly larger risks that cause even more failure. We debate the outcomes of systems more often than addressing the design of the systems themselves. This one insight, if applied to human governance systems, represents the greatest single improvement we could make to global happiness and wellbeing.

• Sapiens, by Yuval Noah Harari, is literally epic in scope, covering the greater arc of humanity at a scale I had not contemplated before. Fire, religion, capitalism, enlightenment, corporate personhood, democracy — there are a handful of key ideas that additively changed our collective fates. If anything, Sapiens recounts how the greatest of human systems (e.g. the cooking of foods, the advent of agriculture) have shaped the lives of everyone today.

Money and Finances

• The Intelligent Investor by Benjamin Graham and the annual letters of Warren Buffett for Berkshire Hathaway. “Can one of the most successful investment firms of all time have a website that still looks hosted by GeoCities?” Yes — most definitely, yes. When you are as successful as Buffett and Munger have been, you can afford to have a website that looks like Mosaic rendered it in 1994. The biggest takeaways from Graham and Buffett are the seemingly simplest principles: stocks are the fractional ownership of companies; the market is a voting machine in the short term but a weighing machine in the long; whenever you buy a stock at a certain price you think is a good deal, someone is selling it to you because they think the exact opposite; we’ll know who’s swimming naked when the tide goes out; buy great companies at good prices.

• The Truth About Money by Ric Edelman. There are far more books with everyday money advice nowadays, like Rich Dad Poor Dad, and I’ve also not reread this book since it came out over two decades ago so I hesitate to vouch for it. But The Truth About Money influenced me a lot in my early 20’s, just as I started to earn my own money, by encouraging two things: a) saving when you’re young and investing in a diversified portfolio, and b) treating your house as a place to live, not as “your biggest investment.”

• The Psychology of Money, by Morgan Housel, is a contemporary book which I do vouch for and highly recommend. It’s the one book I purchased for each of our kids when they began to earn their own incomes. Far more important than sage investment advice is understanding how your psychology dictates financial outcomes far more than any clever strategy. This book is modern wisdom in the guise of financial advice.

• Die With Zero, by Bill Perkins, is an amazing book saddled by a terrible title. Did you know that the average American receives their inheritance in their mid 60’s when their parents pass away? How much do you think you’ll need your parents’ money by the time you’re in your 60’s? This book single-handedly changed the way we think about giving to our kids. Our plan is now to give them their inheritance in their 20’s to early 30’s — an age when our own lives would have been most improved by an injection of money. My other takeaway is that you’ll die a hundred deaths before your final, physical death. There will be a last time you lift your child up in your arms; a last time you ski; a last time you ride a boat; a last time you travel internationally. The insight is that most of those times, you don’t realize it’s your last time. Knowing this, you should arrange bucket lists for every 5 years in your life as opposed to having just one big Lifelong Bucket List, front-loading activities you may not have the interest or ability to do later in life.

The Self

• Solitude and Leadership by William Deresiewicz, who also wrote Excellent Sheep: The Miseducation of the American Elite and the Way to a Meaningful Life. As Susan Cain wrote in Quiet, America values the loud and brash leader who stands out front. But there’s value in the contemplative leader who in fact speaks not as a way to garner attention but as the inevitable outcome of having thought through and reached an important conclusion. Solitude and Leadership was Deresiewicz’s address to the cadets at West Point to remind them that true leadership cannot just be the remixing of thoughts whipped together from 8 hours of nonstop meetings every day of the week. True leadership requires the space and solitude that nurtures novel insights.

• Citizenship in a Republic, Theodore Roosevelt’s 1910 address at the Sorbonne. “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” If you judge all past writings through the lens of modern conventions, you’ll pass a kidney stone at Roosevelt talking about women cooking. But an inability to see past that would blind you to a host of wisdom around our higher calling to make for us a great democracy, and to reflect on the type of men and women required to sustain it.

• The short stories of Alice Munro. I didn’t want to just focus on Hateship, Friendship, Courtship, Loveship, Marriage: Stories — winner of the Man Booker Prize — or just on Alice Munro, for that matter. I wanted some representative of the importance of fiction in shaping one the most important aspects of my life, which is how I think of my relationship to others. The Great Gatsby, A Separate Peace, Of Mice and Men, To the Lighthouse, The Lord of the Rings, The Fault in Our Stars, Les Miserables… there are just too many to name. One of the greatest strengths of fiction is to remind us what we already know but have been blinded to by the barrage of everyday life. Munro’s writings consistently do that by exploring the space between us.

I’m sure I’m missing plenty from this list, but it’s a start. I’d be interested to hear some of yours in the comments!

Fireside True Story™ Time: It inverts causality to claim that Caleb’s Guide, the book I wrote for my son as he headed off to college, represents life-changing perspectives most influential to me, but I was reminded of it when gathering the list of readings for this article.

I wrote the book several years ago as my son was leaving home because the end of my concentrated time with him was suddenly drawing near. All the years I had thought I would have to convey insights or wisdom had passed much more quickly than I expected, leaving me little time to say things I felt were most important to say.

So I wrote Caleb’s Guide to collect snippets of my insights around life, careers, finances, and relationships. Caleb has the world’s only hardback edition, though the softcover is available to anyone through Amazon.