Recommended Reads

Below I share books that have shaped me in different ways:

• Most influential
• Most moving
• Most delightful and fun to read
• Most useful

Most Influential

Siddhartha by Hermann Hesse

This is the single most influential novel I’ve read. It’s a two-hour delightful read that tells the story of a character named Siddhartha on a parallel journey to the Buddha on the path to enlightenment. It serves as a reminder that we must all craft our own journey through life. We must learn by being, not just reading.

There are so many themes packed into this short novel that it’s hard to know where to start. The one that strikes me most is the tension between experience (wisdom?) and knowledge — how there are severe limits to what can be thought or conveyed through words or ideas alone. Ironically, it was the experience of walking the Camino de Santiago — a weeks-long pilgrimage across Spain — that led me to experientially understand the importance of experience over knowledge. I might have read sections about how there were things that could not be learned from a teacher, but I certainly did not appreciate or understand those bits until I’d lived them. The novel is also a powerful reminder of our preoccupation over trivialities and our fictionalization of concerns — especially at work, echoing characters who lose themselves in commerce and routine. And finally, it’s full of departures — a son leaving his father, lovers parting ways, a parent watching a child walk away — that tap into something universal about growing up: the guilt and grief of leaving the people who love you most, knowing you’ll never really come back in the same way. What a gold mine of themes and ideas!

Brave New World by Aldous Huxley

This book was influential to me due to the timing — it served as a reminder to challenge all assumptions about the world around us. The things that we learn are conditioned to us from birth by our education system, and very little of our thinking is truly independent. Brave New World served as a wake-up call for questioning assumptions I have held most my life.

Sex, Ecology, and Spirituality by Ken Wilber

The book outlines Wilber’s integral theory — essentially a universal theory of philosophy, science, consciousness, and culture. It does so by characterizing the nature of the world as being composed of holarchies: in essence a hierarchy where each level in the hierarchy is both a whole, and a part of the next level. Growth in each hierarchy involves transcending the current level by negating it, but then preserving and integrating it. This mental model helps explain inner consciousness development, the physical material world, culture, and observable cognitive development — and the levels of these hierarchies are related across all dimensions. Personally, what I take away from this book is the simultaneous pursuit of Ascent and Descent — of striving towards deeper and deeper transrational consciousness while embracing a love for the world as it is. More broadly, I take away the notion of integration: I can learn from a diversity of perspectives, most individual perspectives are incomplete, and integrating them is one of the most profound tools for developing deeper consciousness. Overall, a book I’d highly recommend to anyone looking to expand their way of thinking and being in the world, but it’s very dense.

Most Moving

When Breath Becomes Air by Paul Kalanithi

The most emotionally moving book I have ever read — the story of a neurosurgeon who passes from brain cancer. I spent four hours more or less continuously crying while reading the book in a single sitting. Kalanithi paints a beautiful and devastating picture of mortality.

Steppenwolf by Hermann Hesse

I see myself in this novel; torn between a multitude of personalities and identities that I apply in different situations, with a split mindset between generations. It’s a gripping psychological fantasy novel that reflects tensions in Hesse’s underlying identity as half-man and half-wolf.

Being Mortal by Atul Gawande

Most of us don’t think about mortality much on a day-to-day basis, but it’s one of the most defining parts of the human experience. This book prepares us for mortality and how modern medicine treats death.

Makes you see aging in a different light. Before reading this, I assumed that putting a parent in a nursing home was mostly a sign of neglect. This book completely changed that view — and opened my eyes to the kinds of new alternatives that can make the end of life more meaningful. Full of content and ideas that I had never heard or read about. I will take away many lessons from this book for the care of people around me who are important to me, and for myself (hopefully many years down the line). Extremely moving, brought me to tears many times.

Most Delightful and Fun to Read

The Three-Body Problem by Cixin Liu

A brilliant sci-fi book, so fun to read. I put it down the first two times I picked it up because the prose is bland — but the story is gripping. The cultural commentary is insightful, and it exposed me to the idea of “new science,” i.e. scientific paradigms that we have no conception of today, that are beyond observation with our current tools, but that may contain truths about our universe. I’ve read very little that feels as creative and imaginative as this book.

Don Quixote by Miguel de Cervantes

The first novel ever written, and a very, very funny story. I enjoyed this as part of learning the history of the novel.

One of my favorite books, a delight to read. I never realized how funny a novel could be until reading Don Quixote. The novel pulled me back every week for another fifty pages, and never became tiresome. It brought me a reminder of literature for literature’s sake, as opposed to literature for ideas (although I certainly took away that meta-level idea). Its episodic nature made it particularly fun, like a sitcom in a book. It also serves as a reminder of the strangeness of humanity: it’s not just today that people’s minds are strange, but it’s always been so, and if anything we’re more moderate and tempered and uptight than ever.

The Rosie Project by Graeme Simsion

The book is a story of a person with Asperger’s and how he views the world. The portrait it paints is so vivid, and helps step into someone else’s shoes better than almost any other novel I’ve read.

Brief Interviews with Hideous Men by David Foster Wallace

This is a short story collection, and has the most riveting prose of anything I have ever read. The sheer brilliance of most of the short stories more than makes up for the ones that are maddeningly difficult to get through. The collection gets its power from its brutal honesty and its incisive character portraits — I’ve never seen depictions of people like this anywhere else. Wallace exposes the emotional perversions of his characters with an honesty that reminds you we all have hidden ugliness, and that we can do better to confront it (at least in ourselves). The anger can get a bit exhausting at times, but as a whole the collection is just brilliant. Besides the content, it’s stylistically phenomenal: the wordplay, the structural play, the meta-fiction on meta-fiction, the lens into how Wallace writes his stories in the first place (Octet), the footnotes, the omissions of responses in dialogue. I’ve never seen anything quite like it. Some moments that stood out: the man who counts a woman’s orgasms being just as hideous since people crave to please their partners too; the inability to communicate the feeling of depression; the recognition of self-absorption and that trapping the person listening. Honestly just so many vivid feelings that I’ve never seen captured quite this well anywhere else.

Most Useful

The Mom Test by Rob Fitzpatrick

This book is a must if you’re starting a company or building products. It talks about how to get user feedback: if you ask someone about an idea you’re working on, they’re bound to say it’s good (like your mom would), just to make you happy. This book sets up fantastic frameworks for getting actual user feedback. Implementing it is much harder than it sounds!

This book feels like an application of the scientific method to customer conversations — something that’s natural for a skeptic. It’s also one of those books that people love to evangelize and then do exactly the opposite of — I’ve watched people ask leading questions and then declare “see, everyone loves what we’re building!” Some of the biggest takeaways:

• If they haven’t already tried to solve their problem, it probably isn’t that big of a problem for them.
• Dig around at emotional signals — when you’re building technical products, it’s easy to focus only on the tech.
• “What are your big goals and focuses right now?” is a great question for understanding people’s priorities.
• Talk to the multiple people who could be failure points — you’re not usually selling to a single person.
• Don’t overdo the meetings — they’re about quickly learning what you need.

The Defining Decade by Meg Jay

Jay writes about the 20s and how the decisions we make in our 20s impact the rest of our life. A lot of it could be summarized, but reading it fully helps the lessons internalize and helps lead a life with less regret.

A refreshing, quick read and a relatively standard self-help book. There are three major sections. The one on your career is interesting if you’re not already ambitious; in my case, it felt mostly like a reminder that the decision was in my hands about what I would end up doing. The one on relationships is probably the most broadly useful. It’s a good antidote to the commitment-averse tendencies you see in Gen Z and Gen Alpha — the instinct to keep all options open, to treat doubt as a dealbreaker rather than a normal part of being with someone. The final section on mind and body was probably the most useful to me, and to most ambitious people. The core idea — that twentysomethings with overactive amygdalae often want to change their feelings by changing their circumstances, quitting things that get messy rather than sitting with necessary imperfection — really resonated with me and was a strong reminder of how tempting it is to run from challenges instead of through them. The final remarks on fertility statistics were a good reminder of why it’s worth thinking about having kids earlier than the coastal elite default, and accounting for that in your planning.

Flourish by Martin Seligman

This book outlines a framework for human flourishing. Seligman breaks down the primary ingredients of a meaningful life into five elements — Positive emotion, Engagement, Relationships, Meaning, and Achievement (PERMA) — which helps clarify where to actually devote mental energy. Too much of our modern world is focused on achievement alone over personal fulfillment and connection with the people around us, and this framework is a useful corrective for rebalancing.

Never Split the Difference by Chris Voss

The best handbook for negotiation ever written! Brilliant, and full of actionable advice. Some of the takeaways that resonate with me most strongly right now include: using calibrated (“how”/open) questions to get the other person to work to solve your problems (“How am I supposed to pay that much?” e.g., or “Where can I find that money?”); saying no softly (“I appreciate that offer, but that won’t work for my budget.”); using specific numbers (this one still feels weird, but is likely effective despite that); preserving the decision maker’s agency, and understanding their non-monetary factors at play (often will be black swan factors — maybe the person is up for promotion?); labeling the other party’s fears/emotions/concerns as a way to abate them (“You may be worried that we are young founders.”), in particular pause after stating a label to allow them the space to respond; getting no answers over yes (no maintains agency, yes feels like something you say to get the conversation over with).

No Bad Parts by Richard Schwartz

Insightful (but not exceptional as a read). Mostly gave it five stars because I suspect it will have a deep lingering impact on me three months from now. It’s one of those kinds of books that steeps into my mind and will stay with me as a lens.

There’s a good chance that this book helps me discover the source of a handful of patterned behaviors that irritate me — I’ve solved most of my general stressors but there’s still a handful that linger and create nuisances for me.

The most revelatory part of the mental model to me was thinking of parts as: 1) in multitude — I’ve often thought of people as having a couple of parts at most, sort of like Steppenwolf, but never a multitude, 2) wholes, in and of themselves — each emotion reflects an identity that’s operating in the driver’s seat, and 3) as third-party identities, where I can ask what is “it” angry about instead of what am “I” angry about, which changes the mental model.

Excited to see what tangible impacts this book makes on my life.

Scaling People by Claire Hughes Johnson

An excellent book that I read at the perfect time for myself. This book is full of tactical advice for how to scale organizations, improve interpersonal dynamics/relationships, and uplevel yourself and others. It’s one of the only resources I’ve found that has actual tactical, operational advice for people management. If you’re a very intentional leader, you might learn many of these things on your own over time, but I was encountering many of them for the first time as my org hit ~20 people while I was reading the book. Most other books on people management are philosophies/platitudes/generalities, not tactics that are tangible and implementable. If you’re looking for tactical advice for improving people management, this is the place to go!

Outlive by Peter Attia

Outlive was way better than I expected. I really wanted to dislike it (especially given I dislike the people who appear to be Attia-cult-followers all throughout Silicon Valley), but it was a fantastic read.

What I appreciated most was Attia’s encouragement to think for yourself and not follow rules dogmatically (ironic, since his cult following has turned this into a dogma). This led to plenty of interesting questions and self-reflections as I read the book.

A couple of the things I have significantly more appreciation for compared to going into the book: the importance of stability exercise (this clicked for me as a core part of the reason I have different pains), protein (always thought it was important, but may be even more important and the reason I’ve not bulked muscle), and dietary control for avoiding metabolic syndrome (which I appear to have a mild version of already, probably from eating massive meals and a high-carb diet).

It’s also a refreshing perspective on medicine that I’d encourage new residents/med students to read.

Finally: I’m fascinated by the ways in which people can expose society to a new idea in the zeitgeist. Attia managed to popularize the notion of longevity in the mainstream. What a remarkable feat!

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You can see more about all of the books I’ve read here.