The Year of Magical Thinking - Joan Didion

This is a deeply personal book about grief. The Year of Magical Thinking speaks to the raw emotions that follow Didion after the loss of her husband. As I read, I couldn’t help but trace the parallels between Didion’s telling of her husband John’s death and my mom’s experience (and, obviously, the whole family) coming to terms with my dad’s passing. The suddenness, the recounting of the scene, the constant what-if’s, and the sheer disorientation of becoming untethered from a life partner, all seemed too familiar.

She quotes C.S. Lewis, on the haunting notion of having to navigate the world without a partner who’s no longer there: “So many roads lead thought to H. I set out on one of them. But now there’s an impassable frontierpost across it. So many roads once; now so many cul de sacs.”

Though Didion passed away at the end of 2021, her book was at the top of my list before then. The Year of Magical Thinking did not comfort me, nor did it bring me catharsis, but reading it somewhat clarified my thoughts on the complex and confusing experience of losing someone dear, and grieving, by letting me see it through someone else’s eyes. This is a tough book.

The Bonfire of the Vanities - Tom Wolfe

This is one of those books I’d heard mentioned many times, but I had no idea what I was getting into as I started reading it. The Bonfire of the Vanities is a novel set in the ’80s that discusses the structure of society, with criss-crossing cuts of race, class, religion, occupations and more.

The plot centers around Sherman McCoy, a New York financier, and his fall from grace after a hit-and-run. Much of The Bonfire of the Vanities focuses on the distinction between reality and appearances, and how facts and intentions don’t really matter when our actions are perceived as transgressions of a social contract. This is explicit in the journalistic treatment of McCoy and the judicial case that follows his accident, but also hinted at repeatedly throughout the story. For example in discussing the field of finance and its relationship with “the real world,” McCoy repeatedly struggles to explain how he brings value to the world as a bond trader. The value he creates is detached from the tangible, manifesting instead in the abstract movements dictated by the whims of the market. That is just another flavor of the same idea: others’ perceptions affect our reality, and the value we ascribe to things.

The scene when McCoy reflects on his identity after being ostracized by friends and neighbors carries the central message of the book. After being arrested, McCoy realizes his life is only defined by others around him: “Your self… is other people, all the people you’re tied to, and it’s only a thread.” Our identity, our self-worth, and our meaning are defined by others. I might do a longer blog post on this idea down the line.

How To Change - Katy Milkman

I picked up How To Change after hearing Milkman on Russ Roberts’ podcast, Econtalk. Roberts tends to be really skeptical of pop psychology, so I gave his positive review a heavier weight than usual. The book contains the self-help advice that you’d expect, but backed by repeated studies and theory. Milkman repackages these ideas into “choice architecture,” a systematic approach to how we present options to ourselves. She argues that much like economists and politicians think about governance and policy one level of abstraction up, so should we: not focusing on individual decisions, but the incentives we set up to make it easier to choose behaviors that are aligned with our goals.

Among many other examples, Milkman discusses strategies like “accountability partners” and public commitments as ways to change our habits. She showcases replicated experiments on simple ideas like writing down our goals, or telling our friends what we’re aiming at. She also explains how she coined the term “temptation bundling” to describe a behavior we’re all familiar with: pairing a desirable activity (like watching TV or listening to podcasts) with a less desirable one (like exercising) in order to incentivize the latter. These approaches toward self-control are not particularly innovative, but it is useful to see them all listed back-to-back. Milkman does not pretend that these are one-size-fits-all, but instead suggests that we should mix and match the tools she presents to achieve real, permanent change.

The Plague - Albert Camus (translated by Stuart Gilbert)

A classic existentialist novel, The Plague narrates the story of a small town suddenly affected by an epidemic that decimates its people. In a volume that feels all too familiar in the 2020s, Camus’ characters’ lives intersect with the outbreak in all sorts of uncomfortable ways. There’s those whose life projects are stopped in their tracks, those who try to help others combat the plague directly, and some that only care about saving themselves at the expense of their neighbors.

Camus prompts us to reflect on our meaninglessness by critiquing the institutions of government, church, and even journalism. He does not outright condemn these, but rather presents them as tools which humans use to grapple with the challenges of existence. He highlights the complexities of faith and the limitations of institutions when confronted with the harsh realities of suffering and death. The Plague invites readers to reflect on the nature of faith, moral responsibility, and the potential for false hopes in the midst of existential crises.

Ultimately, the point Camus tries to get across is that life is a succession of minor plagues that we must face. There is no new normal, just normal.

Inside Out - Nick Mason

This was the first of many rock musicians’ biographies that I’ve read recently. Mason is one of the lesser-known founding members of Pink Floyd, and Inside Out is his telling of the band’s rise to fame. The original members, including Mason on the drums, met while they were architecture students in London. A good chunk of the book is devoted to their personal conflicts: lead guitarist Syd Barrett’s deteriorating mental health, his successive replacement with David Gilmour, and the eventual tensions that broke the original crew.

A recurring theme in the book is that while they were gaining traction, the bandmembers were not particularly aware of their significance within the broader music scene. Mason goes into detail explaining how the band’s style evolved, from the early days exploring recording experimental pieces and focusing on moods to the flashy performances of their world tours. He also tells of the eccentricities he and others indulged in as the money started pouring in. Cars, island homes, and private studios went hand in hand with interpersonal conflict, and Mason isn’t shy about sharing either side.

The book doesn’t feel ghostwritten, and is full of fortuitous anecdotes of what the band experienced on their way to the top. Some of those contingent moments really stayed with me, from the spontaneity with which they chose the name Pink Floyd, to the time that their van was broken into and Mason’s mom lent them £200 to replace their equipment, or the time at Abbey Road Studios when the band realized they were recording next door to The Beatles and their producer Norman Smith was able to sneak Mason and friends in to see them record. The book honors its title, sharing many of the inside stories of a great band.

The Sovereign Individual - James Dale Davidson and William Rees-Mogg

I believe I first heard of The Sovereign Individual in a tweet or HN thread that described it as having “a startup idea on every page.” While it didn’t live up to my expectations in that sense, the future they speculate is a profoundly interesting unbundling of modern society, and it makes a great read. I’ll grant that many of the ideas resonated with my own biases, but it’d be hard to argue they are not at least plausible.

The core thesis proposed by Davidson and Rees-Mogg is that as technology advances, individuals are able to exercise greater control over their finances, and thus their lives. In short, they predict that the internet and encryption will reduce state visibility into people’s wealth and income, to the point of the decline of traditional nation-states (see what I said about biases?). The Sovereign Individual emphasizes privacy-preserving peer-to-peer technologies as tools to resist coercion in this new era, foreshadowing the eventual rise of cryptocurrency in the 2010s. It’s hard to believe this book was first published in 1997.

While there have been significant geopolitical changes since the book came out, the pace and extent of these shifts have not led to the predicted weakening. We have not yet seen the erosion of state authority pushed by the authors, but wealth preservation and tax avoidance techniques that were previously only available to the ultra-rich are now within the reach of many. Yes, this book panders to the crypto crowd. And yes, it stretches reality to fit with its libertarian tendencies. However, the vision and the foresight to write this 25 years ago are commendable.

Los Detectives Salvajes - Roberto Bolaño

Los Detectives Salvajes is a sprawling book about a group of young poets and their adventures in the 1960s and ’70s in Mexico. Reading it, I kept wanted to discuss the places and the people with my dad, who was a college student in Mexico City in the early ’70s. Bolaño tells a self-discovery story as the group searches for meaning and identity as they live the rebellious spirit of the time. Through a wide cast of characters, the novel explores the transformative power of art and the chaos of life, while constantly blurring the lines between reality and fiction.

The novel centers on Mexico’s counterculture through feuding literary movements. It does so by telling individuals’ deeply intertwined stories. The characters in the book are stand-ins for the author and his friends, while a few others are just representations of themselves - like Octavio Paz. With its fragmented and non-linear narrative, it reminded me of Córtazar’s Rayuela. It heavily reflects the political and social upheavals of Latin America during the 20th century, including snapshots of the Mexican student movement and the dictatorship in Chile (where Bolaño is originally from). Los Detectives Salvajes was kind of a slog. I enjoyed its themes, but between its length, its confusing narrative, and the deep cuts of Latin American history and literature, I doubt most people reading this blog would enjoy it.

Phaedrus - Plato (translated by Robert Scully)

Last summer, I was lucky to join one of the few in-person courses hosted by the Catherine Project reading Plato with Zena Hitz and a few folks at the Berkeley Institute. Phaedrus was my first ever foray into Greek classics, and I probably would not have jumped in without their guidance.

The dialogue is a reflection on love, our inner motivations, and the nature of knowledge. It kicks off with an almost modern discussion about the difference between speech (a proxy for knowledge) and the written word. Phaedrus had heard Lysias speak, and Socrates asks him to recite his speech. Phaedrus holds a written copy of the speech, and the distinction between the original and his adapted versions take center stage. The dialogue discusses whether speechmaking is good or shameful, and whether being able to repeat something is the same as knowing it. Socrates looks down on rote memorization, while at the same time seeming to equate it to writing.

Plato also introduces the allegory of the charioteer, depicting human souls as being composed of three parts: a charioteer who represents reason and intellect, a white horse who represents our virtuous side, and a dark horse who represents our base desires. While the allegory implies a Manichean dichotomy of good and evil, at surface level it is about discipline and self-control. In our group, the analysis quickly turned recursive: does the charioteer have his own set of horses and charioteer? Do the horses? Without trying hard, the conversation devolved into an argument on free will.

Although the sections about love went way over my head, I found the rest of the discussion intriguing, particularly after the third speech. The fact that these dialogues were recorded nearly 2400 years ago and continue to resonate today speaks to the timeless nature of human inquiry and our philosophical questions about knowledge, morality, and reality.

Master and Man - Leo Tolstoy (translated by Aylmer and Louise Maude)

I decided to read this novella for a mini book club that Russ Roberts hosted on Econtalk. The story centers around a wealthy landowner and his servant, who set out on a journey to a neighboring village for a business deal during the winter. As the weather worsens, they get lost in a blizzard. The landowner’s greed and self-interest are exemplified in his relation with his family as well as his shady business dealings. His attitude contrasts starkly with the servant’s humble nature as they face the storm together.

Master and Man is short and worth a read, so I won’t spoil it. The conversation between Roberts and his guest Richard Gunderman is a wonderful exploration of morality, values, and meaning. In classic Econtalk fashion, they discuss the characters’ actions by reflecting on Russ’s favorite Smith quote — “Man naturally desires, not only to be loved, but to be lovely” — and how Smith’s notion of love relates to self-interest. In a Hobbesian state of nature, we may act generously, not solely out of pure altruism, but because being seen as generous makes us more likable or respectable. Our actions are influenced by our desire for social approval and the way we wish to be perceived by our peers. Tolstoy’s story, on the other hand, highlights the Smithian view, where humans can go beyond the simple second order effects and realize the value of selflessness beyond mere social approval, understanding that genuine generosity can lead to a richer, more meaningful life. Tolstoy’s story challenges us to reflect on our own motivations and the true nature of our actions.

The Overstory - Richard Powers

A novel that advocates ecological thinking, and shows we are often connected in unexpected ways. Powers narrates the story of seemingly disparate characters, whose lives are gradually revealed to be intertwined through their connection to trees. While the themes are clearly about conservation and sustainability, The Overstory felt fresh and interesting, not preachy.

Spanning time and space, the novel covers a century of immigration stories, local and global. Powers’ book paints a vivid image of the US melting pot – from great-great-great grandpa Hoel planting trees after moving to the US from Norway, to that of Winston Ma fleeing China and raising his family here, or Neelay Mehta growing up in Silicon Valley. At times, the connections seem too contrived, and some of the story lines extreme, but they remain plausible within the narrative.

As the story unfolds, each character undergoes a transformative moment that links them to the natural world and to one another, awakening their sense of responsibility towards the world we live in. We’re all linked, and The Overstory serves as a powerful reminder of the interconnectedness of life.

The Power Law - Sebastian Mallaby

A history of venture capital from its early days to the present, The Power Law explores the impact of this growing segment of the fiancial world on the technology industry and the economy as a whole. In its opening pages, Mallaby explains “the Valley’s most bracing creed: the belief that most social problems can be ameliorated by technological solutions, if only inventors can be goaded to be sufficiently ambitious.” He continues, “Venture capital was not merely a business; it was a mindset, a philosophy, a theory of progress.” This idea is alive and well today and its echoes still run through the Valley.

Mallaby begins at the beginning, from the mid-century military origin of research in the Santa Clara Valley region of California when it was all oranges and almond trees, the infamous Traitorous Eight, and their financiers, Thomas J. Davis Jr. and Arthur Rock. He continues through venture’s greatest hits, from Apple and Venrock to Genentech and Kleiner Perkins. Eventually, he gets past the star-eyed nostalgia and covers more recent homeruns like Google and Facebook, as well as its flops like WeWork or Theranos.

For those of us who live in the Bay Area and have swam in its shark infested waters, the book is in no way shocking. It’s a story about a white boys club paying attention to their bottom line. However, reading the re-telling of specific deals with their details and close calls is edifying. Ideas that in retrospect seem obvious, like the partnership structure of most VC firms, had to be figured out. Mallaby walks through may of these in this book. I’m convinced that the risk taking ethos of venture has been a net positive in the world, and The Power Law provides a good way to grasp its roots.

Safe Haven - Mark Spitznagel

My friend Mike recommended Safe Haven to me when we were both still at Vouch. Spitznagel is one of Nassim Taleb’s collaborators, and Safe Haven merges a lot of insurance and investing topics, taking a pretty deep dive into the barbell investment theory that Taleb popularized. The book is about investing in tail risk hedging strategies to avoid ruin, which should not seem like a coincidence if you’ve read Taleb.

The book was pretty high level, scant with examples, but the one takeaway I got from it was to think about investment projects by using geometric instead of arithmetic means. Spitznagel uses the example of a sailing company going on repeated trips and reinvesting his gains with and without insurance on their ships to illustrate this idea. Paying a small cost to insure each trip means that on average there’s a smaller chance of ending up with zero returns to reinvest halfway through. Arithmetic returns are calculated by adding up the individual returns for each period and dividing by the number of periods. Geometric returns, on the other hand, are calculated by multiplying all the returns together and then taking the nth root. This simple difference allows us to account for compounding effects. By using a cost-effective risk-mitigation strategy, investors can reduce the overall volatility of their portfolio and increase its geometric average return, which can lead to higher long-term returns even if the arithmetic average return is lower.

Safe Haven rails against plain expected values. As Spitznagel points out, “You get what you get, not what you expect.” For most people, this is probably not a book worth reading, but that one insight alone is extremely valuable.

Souls on Fire - Elie Wiesel

Though mostly known for his first-hand account of the horrors of the Holocaust, Elie Wiesel’s later work explores the Jewish experience more broadly. In Souls on Fire, he leans on his upbringing in the Hasidic community of Sighet, Romania, and opens a window into the world of Hasidism. Hasidic thought emerged in Eastern Europe in the 18th century. Spearheaded by the Baal Shem Tov as a reaction to the academic elitism of the Jewish establishment, Hasidism intended to make Jewish spirituality accessible to the masses, encouraging a disintermediated personal connection between God and every Jew. The book is a collection of tales of the movement’s founders and followers, including light commentary aimed at the modern reader.

Seamlessly blending historical fact and parable, Wiesel presents how these communities saw themselves, and how their spiritual leaders inspired hope in a turbulent context. The leaders are portrayed not just as religious figures, but as therapists and advisors, bridging esoteric religious ideas to universal human experiences.

As a philosophical worldview, I’m laregly allergic to Hasidism. Like other flavors of what has become Jewish orthodoxy, it stands in opposition to much of scientific rationality, welcoming contradiction and mystery as a natural part of human existence. At the same time, Hasidism also highlights the relationships between people as a central value, emphasizing family, community, and the role of the rebbe as a sage whose experience and wisdom guides others. Wiesel points out that “the Baal Shem’s major concern was to create links at every level. To him, everything that brought people together and consolidated the community was good; everything that sowed discord was bad. […] Man’s role is to mitigate solitude; whoever opts for solitude chooses the side of death.” The idea that we derive value and meaning from community and interconnectedness is clearly present in the book. Engaging in acts of kindness and justice for the sake of community-building, as opposed to some divine objective good, resonates with me, and the selection in his anthology shows that it resonated with Wiesel, too.

One Day in the Life of Ivan Denisovich - Aleksandr Solzhenitsyn (translated by H.T. Willetts)

One Day in the Life is a damning account of life in the Soviet Gulag system. The novella follows its namesake on a single day in his ten-year imprisonment in a Soviet labor camp. Wrongfully accused of espionage after being captured by the Germans during WWII, the main character endures the grueling routines, scarce food, and harsh conditions along with his fellow inmates. The book remarkably passed Soviet censorship and was published in 1962, revealing the extent of human suffering under Stalinist repression in the camps. Laying out the oppressive nature of the regime in great detail, I’m surprised that the Russians allowed it to reach the public, and even more suprised that Solzhenitsyn would be brave enough to submit it to a publisher.

The most striking aspect of One Day is that it is supposed to be a narration of a single unremarkable day. Where we see brutality and intensity we are really supposed to be shown what was normal for Ivan, ordinary moments in any zek’s life. To an extent, this is Solzhenitsyn telling his own story, and that of the people he met in the camp. Reading it made me want to bump The Gulag Archipelago a few slots in the queue.

The Manager's Path - Camille Fournier

The Manager’s Path is a practical guide for engineers growing into managers. Drawing on her experience as a technical leader, Fournier offers actionable advice for each stage of management. The book is structured like a ladder, starting with an individual contributor learning to be managed and managing up, covering fundamental aspects of Silicon Valley management culture like 1-1 meetings, skip-levels, feedback, and career growth. It quickly transitions into mentoring, tech leading, and managing individuals, teams, and eventually multiple teams and managers. She addresses the challenge of choosing the IC or management tracks, and the skills needed for each. Having chosen the manager track myself, I found her commentary on debugging dysfunctional teams and people drama to be quite relatable. While she discusses senior leadership and strategic priorities, this section felt more obligatory than insightful.

My main takeaways came from the sections on giving and receiving feedback, and making sure team members trust you enough to express their goals or seek guidance in discovering them. She also had very strong views on culture and leadership, pointing to Andy Grove’s take on a manager’s cultural values as guideposts for their team decisions. Doubling down on that idea, she writes about Apple employees invoking the spirit of Steve Jobs as a way to “argue for and against decisions, as a compass for what the organization should be doing.” Having been in those rooms, with those people invoking that spectre, I can attest to the power of that idea. Culture is mimetic.

A great manager curates processes and people for the team to make better decisions with less effort. Fournier’s book is good for those considering the management track, or looking to grow within the role by paying attention to the human side of team-building.

Project to Product - Mik Kersten

One of my realizations of 2022 was that I needed to get stronger at product. In retrospect, Project to Product was not a good choice to level up there. The book focused on larger organizations and how to transition them to develop software using Kersten’s framework on “value streams,” an idea that just didn’t stick with me. According to Kersten, while standard software development focuses on delivering discrete features efficiently, in either agile or waterfall-like project management styles, value stream-oriented development prioritizes the continuous delivery of value across the entire lifecycle of a product. It was unclear how this would be different from well managed agile where all activities across teams are aligned to maximize business outcomes.

The book is full of case studies and examples, but I found them unrelatable. There was a whole section about Boeing and why taking risks there is discouraged, which was memorable because it reminded me a bit of certain aspects of Apple’s culture. Beyond that, I didn’t have many takeaways, as the lessons were not novel enough to make the book engaging. I was hoping for more practical advice on how to make product decisions, but instead got a consultants’ reframing of lean manufacturing ideas applied to old software firms. In the end, I ended up giving it away to a friend at Boeing who was dealing with the specific issues covered in that section after being promoted to management. I hope it was more useful to her than it was to me.

Family Lexicon - Natalia Ginzburg (translated by Jenny McPhee and D.M. Low)

This might have been my favorite book of 2022. Ginzburg writes about her family life growing up in an atheist Italian home with mixed Jewish/Catholic roots during the rise of fascism. Mixing fiction and memoir, Ginzburg weaves narratives at two levels, taking us through mundane moments with neighbors and family friends that defined her early life, while also zooming out to the broader political context surrounding her family.

The comedic scenes, like her dad cursing about apples or her siblings fighting over nothing at the dinner table, are counterbalanced by tense episodes when the fascist backdrop comes to the surface. Some are subtle, like the notes of German trucks coming and going, or the self-censorship depending of which acquaintances were around. Others are much more explicit, like when the author describes how her brother Mario escapes the fascists by jumping in a river and swimming across to Switzerland, or more poignantly how after moving to Rome she writes as a side comment: “Leone was the editor of a clandestine newspaper and was never home. They arrested him twenty days after our arrival and I never saw him again.” Such stark illustrations of the harsh reality of life under a repressive regime, and the toll it took on those who opposed it, are layered with lighthearted scenes at home, a sad reality of mid century Europe which the author masterfully narrates.

Reading Family Lexicon was also an interesting exercise in translation. I worked through it with Hannah, often skipping back and forth between the Jenny McPhee’s 2017 translation and D.M. Low’s 1967 version. It was curious to see which sayings were translated the same way word for word, and which ones were slightly different. Ginzburg’s portrayal of family dynamics feels intimate, dotted with inside jokes and sayings that reminded me of my own family’s unique and nonsensical recurring phrases.

Life, a User's Manual - Georges Perec (translated by David Bellos)

When I travel, I like to read books about the places I’m visiting. As we planned our Paris trip I picked up this book based on its translator David Bellos’ own review, which called it one of the top five French novels ever. Life, a User’s Manual is a post-modern novel about impermanence, told through puzzles and filled with layers of complex structure. The book is set in a Parisian apartment building, with each chapter dedicated to a different room, its inhabitants, and the objects within it. The characters and their stories are interwoven throughout the building, along with the city, and their history over decades.

Reding Perec’s book evokes the neologism of sonder - the realization that each random passerby is living a life as vivid and complex as your own. The apparent protagonist helping us thread the story is Bartlebooth, an eccentric millionaire whose life project is to travel the world, create watercolors, and then turn them into puzzles which he solves and destroys. However, on closer reading it’s clear that there is no main character, and that it’s the building itself that we’re supposed to be paying attention to. The building is a fractal of the city around it, which in turn is a microcosm of the world at large. The more you read about one character’s life the more you understand the overarching story that Perec is trying to tell us about the others, and the fleeting experience of life. Perec highlights the accumulation of mundane, seemingly insignificant aspects of daily life as rich with complexity and meaning. These details, immaterial on their own, shape and form our lives. In a way, this can be read as a positive example of the idea that Solzhenitsyn highlights when describing Ivan Denisovich’s grim ordinary day as I noted above.

Despite their ephemerality, the summation of tiny moments we experience are our lives.

The Anatomy of the Swipe - Ahmed Siddiqui

This is a book about the mechanics of how credit cards work. It breaks down the complex steps that make up a transaction, from a card being swiped to the funds settling on the seller’s account. Exposing merchants, banks, payment processors, and even companies that make and operate card terminals, Siddiqui reveals a layered architecture of intermediaries that is invisible to most consumers. After reading Payment Systems in the US the previous year, and being disappointed with the lack of detail, fintech Twitter was quick to recommend this book. It was closer but still not the explainer I wanted.

I was hoping that by understanding the flow of payments, I’d be able to identify a leverage point or a bottleneck, obvious spots to improve the consumer or merchant experience. There are startup ideas buried in The Anatomy of the Swipe, but nothing got me excited enough to go further down the payments rabbit hole.

Wild Problems - Russ Roberts

I often say that studying economics broke my brain. As hinted above, there are few contemporary thinkers who have shaped my worldview as much as Russ Roberts. This book is the crystallization of Russ’s struggle unbreaking his own brain, and helping others like me undo the damage of homo-economicus-style thinking while keeping valuable lessons from the field.

Wild Problems is a rejection of many basic tenets of the economics culture Roberts grew up in. Studying at the University of Chicago under Gary Becker, Russ was steeped in the rational actor model, where every decision could be boiled down to cost-benefit analyses and utility maximization. However, Roberts challenges this reductionist view, arguing that life’s most significant decisions — whom to marry, whether to have children, what career to pursue, etc. — are inherently “wild problems” that cannot be solved with straightforward NPV maximization. He advocates for embracing uncertainty and complexity, recognizing that big decisions are so deeply intertwined with our values and identities that they defy rational analysis. Instead of seeking optimal outcomes, Roberts encourages readers to focus on the process of decision-making itself, embracing the journey and the growth that comes from grappling with life’s toughest choices. Ultimately, we are a product of the sequence of decisions we make in life.

Reading it I kept laughing at how few of the arguments he made seemed novel. I have listened to hundreds of episodes of his podcast, Econtalk, and internalized many of those ideas into my day to day life. Russ seamlessly weaves personal anecdotes, philosophical insights, and diverse thinkers’ views to illustrate his points, making the book both intellectually stimulating and relatable.

The Iliad - Homer (translated by Stanley Lombardo)

Continuing my dive into the classics, I got to study The Iliad with Jonathan Fine and the Catherine Project and captured some thoughts and snippets along the way on this Twitter thread. The ancient Greek poem tells the story of the Trojan War, focusing on Achilles and his rage after being dishonored by Agammemnon. I decided to read the Lombardo translation, which aims for a contemporary tone, and playfully uses as its cover an image of Allied soldiers landing at a Normandy beach, pointing to the book’s enduring relevance.

The Iliad is a book about civilization and the nature of power. The interplay between fate, the Gods’ desires, and human free will drives the narrative in this ancient classic. The blurred lines between gods and humans fascinated me throughout. Zeus and his pantheon often come across as superpowered humans, not omnipotent gods, meddling in mortal affairs for their own amusement or agenda with their own hopes and intentions. Gods interact with humans yet remain apart, wielding control over fate and embodying power beyond mortal reach. This creates a constant tension between divine intervention and human agency, setting a clear power hierarchy and a rough sketch of what humans can strive for.

This was my first time reading a Greek epic, so the narrative structure of the Iliad took some getting used to. Homer’s use of repetition — often repeating messages word-for-word — likely reflects its origin in oral tradition, but also serves as a powerful literary device to show chains of trust and access between characters. The occasional narrator shifts, sometimes even jumping in time to narrate future events, add layers of complexity to the storytelling. These features, along with the graphic depictions of violence and the intimate portrayal of relationships (like the ambiguous nature of Achilles and Patroclus’ bond) make the book feel both alien and surprisingly modern. The deeper philosophical questions raised by the text — the human desire for legacy, the us vs. them mentality that drives the conflict, and our endless search for meaning — resonate today and still shape our culture. Achilles’ existential crisis in Book 9 captures this perfectly: “It doesn’t matter if you stay in camp or fight– / In the end, everybody comes out the same. / Coward and hero get the same reward: / You die whether you slack off or work.” This proto-nihilistic view contrasts sharply with the heroic ideal of eternal fame that permeates the epic, exemplified by Hector’s desire for a glorious death to be remembered for generations. And here we are, discussing both their lives, 3200 years later.

The Odyssey - Homer (translated by Emily Wilson)

Continuing my Catherine Project reading, I turned to The Odyssey. As a sequel to The Iliad, it shifts focus from the Trojan War to Odysseus’ homecoming journey. Its tone is notably subtler, offering a more nuanced portrayal of its characters and less intense storytelling. The Odyssey’s non-linear narrative was unexpected, with Odysseus’ trip revealed in fragments through others’ narratives. The same Twitter thread strings a few of my thoughts as I read.

Glory and memory persist as central themes, for example when Telemachus laments his father ending up “nameless and unknown” (1.236), reflecting a fear of obscurity in ancient Greek culture. However, it might also have to do with the concept of Xenia, their code of hospitality, which is highlighted early and often. Xenia is showcased repeatedly in the first few books, demonstrating how friends and strangers are treated when they show up as guests. People are treated better when their ancestors or themselves had previously hosted the relatives of those who now have to do the hosting, explaining the centrality of glory and memory as vehicles for reciprocity. The consequences of violating these ethics are also obvious in the narrative, as seen in the suitors’ abuse of Telemachus and Penelope’s hospitality, and in the scenes where Odysseus visits Circe, the Lotus-eaters and the Cyclops.

What is acceptable within this framework of ethics is not necessarily what a modern reader expects. Odysseus’ cunning nature and his pride in deception are central to his character, and to the story. His ability to navigate challenges through language games showcases his resourcefulness, and is repeatedly celebrated, but raises moral questions. The book shifts to a moralizing tone in later books, with the narrator directly addressing the audience with lessons, contrasting earlier parables’ open ended nature. Scenes from The Odyssey like the encounter with the Sirens, navigating between Scylla and Charybdis, and Odysseus’ final return are so deeply ingrained in our culture that it’s hard to read them without retrojecting meaning into them from modern works. Adventures far from home and homecoming are themes that resonate across time, making reading The Odyssey fun and relatable, but more importantly it lets us have a glimpse into the earliest forms of shared values in society.

Tribal Leadership - David Logan, John King, Halee Fischer-Wright

When Vouch hired a new CTO, the engineering managers had an offsite to plan for upcoming growth challenges. Tribal Leadership was the lens he provided to guide the conversation. In the book, a “tribe” refers to a group of 20 to 150 people working together closely. As we grew, we’d started forming subgroups with different mentalities and behaviors. While the team was small enough to knew each other’s roles, the leadership team had to understand and leverage these tribal fractures to maintain a cohesive, high-performing culture.

The authors divide organizations into five stages based on language/behavior:

1) Life sucks: Individuals feel alienated and hopeless.

2) My life sucks: People recognize their work life can be better, but are apathetic and disengaged.

3) I’m great (and you’re not): Individuals become competitive and focus on their own achievements.

4) We’re great: Collaboration/shared values become drivers, leading to higher productivity.

5) Life is great: Shared purpose and remarkable outcomes.

Despite its overly simplistic view, and the repeated mistake of equating work-life/life-life, the book gave the EMs a shared language to address team challenges. It’s a useful resource for understanding team dynamics, but not a must-read starting point.

Anarchy State Utopia - Robert Nozick

I was first introduced to Nozick through his experience machine thought experiment, which was the reason I put this book on my list years ago. I knew the book would cover much more ground, but was really surprised when I realized the experience machine is a side comment on a side comment, spanning barely a couple of pages. Anarchy State Utopia is a treatise on libertarianism, trying to argue for it from first principles by hypothesizing the rise of early societies as they evolved out of a Hobbesian state of nature. In Nozick’s own words, “The nature of the state, its legitimate functions and its justifications, if any, is the central concern of this book.” While I agreed broadly with his perception of individual rights and the importance of personal autonomy, not surprisingly, Nozick leans further into libertarianism than me.

Perhaps most interesting was his critique of Rawls and patterned principles of justice, which argues that enforcing a specific distributive pattern fails to respect individual autonomy and choices. I often refer to Rawls’ original position theory, so it was useful to read a strong takedown. Nozick’s critique of coercion, paternalism, and redistributive policies further solidifies his argument for a minimal state. In short, he believes that coercive measures and paternalistic policies infringe upon individual rights and autonomy, and that patterned principles of distributive justice fail to respect the choices of individuals, leading to a static and rigid society. Instead, Nozick envisions a meta-utopia, a framework where diverse utopian experiments can coexist, allowing people to live according to their own values and preferences. Honestly, many of the arguments went over my head, so I hope I can go deeper on a second read.