Companion Reading and Resources

This is a comprehensive list of 80+ books, articles, podcasts and tools that are mentioned in Optionality, laid the foundation for large parts of it, or otherwise build on the main themes.

The page is unlisted and only available to readers, so you might want to bookmark it so you can return to it in future (if you forget, you can always sign up for the resources again using the link in the book).

You can use the buttons below to filter the list for my top overall picks, by different mediums, or by specific topic areas.



Incerto — Nassim Taleb

Taleb is my single biggest inspiration, which makes the Incerto series the logical next step for going deeper on the central thesis of the book. I think Antifragile is his masterpiece, and probably has the least overlap with the ideas covered in Optionality. But it’s also the longest and most belligerent book in the series—many people find Taleb’s tone and style jarring to the point of bouncing off his ideas, which is a shame.

You might be better off starting with The Black Swan or Fooled by Randomness, which are tighter and somewhat less acerbic. Then, once you’ve got his measure, you can tackle Antifragile and Skin in the Game.

Walden — Henry David Thoreau

walden thoreauThoreau was the walking, talking embodiment of ‘fuck-you frugality’. His account of building a cabin at Walden Pond is beautifully poetic, bitingly funny, and always thought-provoking.

There are a few boring and snotty bits, but Thoreau shines as an amateur naturalist (he devotes an entire essay to a war between black and red ants) and dishes up delightfully contrarian broadsides against materialistic society. Walden contains very little in the way of ‘actionable’ content—you will not find discussions of safe withdrawal rates here—but it is definitely the spiritual progenitor for large parts of my own life philosophy.

Stumbling on Happiness — Daniel Gilbert

Stumbling on Happiness - Dan GilbertYou may have noticed I quoted Harvard psychology professor Daniel Gilbert more than anyone besides Taleb. That’s because Stumbling on Happiness is one of my favourite books of all time.

Ignore the cute title: this is not a self-help book, but a guided tour through the problems with happiness research, the difficulty of trying to predict what our future selves will want, a deep dive into hedonic adaptation, prediction errors, and the illusion of a stable self over time. For the cherry on top, it’s a delightful read: unlike most scientists who write popular books, Gilbert is a terrific and funny writer.

Mr Money Mustache’s archives

The facial hair that launched 1000 early retirement blogs. As far as I’m concerned, no-one before or since has come anywhere close to MMM in laying out a beginner-friendly path to financial freedom, both in terms of substance and style.

The only problem is that a lot of these ideas are in the water supply these days: even if you haven’t read MMM, you’ve probably already picked up a lot of his stuff through osmosis, and after a certain point, there’s just not that much more to say (which is why posts have trailed off in recent years). Nevertheless, I still think his archives are the single best FIRE resource out there, especially the era from 2011-2013. Or start with this introductory post, and springboard off into any links that take your fancy.

The Elephant in the Brain — Robin Hanson and Kevin Simler

The elephant in the brainNothing looks quite the same after reading this book. It’s necessarily shallow, with the idea being to write 10 short chapters outlining how the signalling model applies in a bunch of different domains (art, education, love, money, politics, religion, etc), but that structure makes it a perfect introduction for the casual reader.

If you have a contrarian bent, reading Hanson and Simler is like the sweetest crack cocaine. Whether or not you fully buy the thesis, I think this is a genuine ‘quake book’ that gives you a very different lens on the world, and thinking more carefully about how our hidden motives might shape our behaviour.

SpentGeoffrey Miller

Geoffrey Miller - SpentI was already well and truly sold on the ‘consumer capitalism is kinda suboptimal’ thesis, but this book is much, much more than that. I pulled out some of my favourite gems in this tweetstorm, including: why triathlons replaced marathons, the ‘cost density’ of black-market kidneys, why IQ is one of the sexiest traits across every culture studied, why everyone on Tinder competes over who loves dogs more, a huge-if-true theory about parasites and xenophobia, an in-depth overview of the Big Five personality traits, and so much more. If you’re interested in learning more about the evolution of status signals over time, superstimuli, and the machinery of consumer capitalism, this is the single best book to read.

The End of Jobs — Taylor Pearson

The End of Jobs - Taylor PearsonTaylor Pearson is the guy who has singlehandedly done the most to build upon Taleb’s work and make it more legible for a broader public (something I’m also trying to do with Optionality).

The End of Jobs makes the case that not only has it never been easier or more fruitful to become an entrepreneur, but taking a traditional career is arguably now the riskier pathway. Where it really shines is in providing a fully-formed blueprint of how to start an online business, backed up with case studies and examples and strategies. It feels like the perfect companion to popular books like the 4 Hour Work-Week, which are great at selling the dream but somewhat lacking in the specifics.

These lessons apply to anyone who wants to become a more entrepreneurial employee/contractor/freelancer in general, not just those who want to run actual businesses. For example, I’ve found the ’90 day sprint’ system that Taylor popularised really useful for my own goals, and took loads of other notes that I’ve applied to my own projects.

Taylor also has excellent write-ups on e.g. volatility clustering and ergodicity on his blog, and is doing interesting work in long volatility/antifragile investing with the Mutiny fund.

Thinking in BetsAnnie Duke

Thinking in Bets - Annie DukeA professional poker player explains how to think in probabilities to make better decisions. I was already familiar with most of these ideas by the time I read this, so it didn’t blow my socks off, but if you were confused by the section on expected value in Optionality, this is a fantastic primer with a lot more worked examples of making decisions under uncertainty.

Algorithms to Live By – Brian Christian and Tom Griffiths

Algorithms to Live By - Brian Christian and Tom Griffiths

This is my number one recommendation for learning more about the explore/exploit trade-off, which has broad applications beyond what I covered in the book, along with information cascades, basic game theory, and the importance of constraints.

The premise: computer scientists use algorithms to figure out how to search, organise, cache, and schedule tasks in the most efficient way, all of which could also be applied to solve problems in meat-based computers, i.e. our brains. How long should you search for an apartment, or a new employee? What’s the most efficient filing system? Is inbox zero worth striving for?

This book perfectly explained a bunch of things I’d been trying to figure out, and wouldn’t have occurred to me otherwise (I knew very little about computer science beforehand). I doubt you could actually run any of these equations and have them spit out an accurate number, because the real world is so messy, but the mental models themselves are still super valuable.

The Righteous MindJonathan Haidt

Reading this book is like taking an empathy pill. It gets you inside the heads of people from various political tribes, so you can see the world through their eyes. Your opponents are not stupid, or wrong, or evil. They just have a different set of moral taste-buds. This is Haidt’s ‘moral foundations theory’, which is the main subject of the book.

It goes on a bit, and is slightly suspect IMO. But there’s so much other great stuff here that even if moral foundations was total bullshit it would still be one of my favourite books: we get humans as superorganisms, the importance of constraints, altruism and group selection, herd behaviour, the sacred and profane, and social capital.

Haidt also makes a convincing argument that the pursuit of rationality through reasoned argument and logic is largely (but not entirely) futile, which is something I’ve reluctantly come to agree with, having initially been big into the rationalist movement.

Levels of Action — Alyssa Vance

A short essay on the importance of going meta with higher-level skills/activities, which often leads to a higher return on investment for lower-level practices. This was very influential for me, and triggered a major rewrite of the book to focus on principles and values first, then high-level strategies and techniques, with the object-level stuff (‘do this’) taking more of a backseat.

The Stanford Marshmallow Prison Experiment — Hotel Concierge

A much more convincing explanation for the famous marshmallow experiments—that what they are actually measuring is not willpower, or ability to defer gratification, so much as ‘the desire to pass tests’. This has implications for perfectionism, eating disorders, education, IQ disparities, and credentialism. Long and slightly difficult to parse, but one of the best essays I’ve ever read.

Nudge — Cass Sunstein and Richard Thaler

nudge sunstein thaler

To be clear: I am not a fan of the political philosophy of this book, I don’t think Cass Sunstein has covered himself in glory lately, and you should be extremely skeptical of the studies cited (lavishing praise upon the brilliance of Brian Wansink, for example). But it is the best primer I know of on the concept of ‘choice architecture’ and streamlining one’s environment in such a way that it takes no real willpower to change behaviours, which was a big influence on the akrasia section of Optionality.

Atomic Habits — James Clear

atomic habits james clearTBH I don’t really buy James Clear’s core thesis—small behavioural tweaks adding up to large results—or at least, I don’t think it’s all that important. I’ve only ever improved my own habits through rearranging my identity, environment, social circles, or the binding constraints, with all the actual behaviour changes happening downstream of tweaks to the overall choice architecture. But Atomic Habits goes into all that stuff in detail too, which makes it a pretty great read overall, especially if (unlike me) you are interested in trying to do the three-step habit formation thing.

Replacing Guilt: Minding Our Way — Nate Soares

replacing guiltIf you have higher-level akratic problems relating to scrupulosity, guilt over ‘not doing enough’, or burnout, I cannot recommend this series of 40 blog posts (also compiled as a free ebook) highly enough. For the right person at the right time, this is a life-changing read. If you don’t relate to these problems, skip it.

Doing Good Better – Will MacAskill

If you’re interested in effective altruism, this is the single best introduction and overview. MacAskill is a philosopher, ethicist, and one of the founders of this burgeoning movement. Every single day we have the chance to save lives, and the cost of doing so is incredibly low—something like $3400. By giving to effective causes over the course of our careers, any normal person can become a hero, saving perhaps 100 times as many lives as a doctor. Fascinating throughout, easy to read, and some of the most exciting ideas I’ve ever been exposed to.

80,000 Hours Podcast — Rob Wiblin

80000 hours podcast80,000 Hours is a sister organisation to the effective altruism movement that aims to answer the question: ‘what’s the most good I can do with my career?’ The website has excellent career advice even if you’re not interested in EA, a job board, and reviews of various professions. There’s also a free book that compiles the best evidence-based strategies for finding fulfilling careers.

I’m an especially big fan of the podcast, which is a deep dive on all things related to careers, altruism, moral philosophy, long-term economic growth, animal rights, existential risks, and generally trying to make the world a better place. It assumes a fairly high level of background knowledge, and gets right into the weeds of some dense topics, but the host Rob Wiblin is a great interviewer, and offers little asides to help the listener keep up with whats going on. Perhaps start with the Peter Singer or Will MacAskill episodes, and then branch out from there if you enjoy it.

How Rich Am I? — Giving What We Can

Are you part of the 1 percent? This is a neat online calculator that lets you plug in your income and country of residence, and find out how you stack up against the rest of the world. It then tells you how much your standing would change if you donated 10 per cent of your income, and what sort of impact you could have by making that kind of pledge.

How to Be Good — Derek Parfit New Yorker profile

I love this profile of the moral philosopher Derek Parfit, which was written a few years before he died. It gives a great overview of his work and driving motivation, as well as his sheer strangeness as a person, including his increasing dissolution of selfhood and desperation to finish his work before the clock ran down. I have not yet made it all the way through Reasons and Persons, and it’s such a huge commitment that I can’t wholeheartedly endorse it, but I am looking forward to attacking it again soon.

How to Do What You Love — Paul Graham

This classic PG essay is a great deconstruction of the notion of work-life balance, while still maintaining realism about the prospects of success, and probably planted the seeds in my mind for the ‘work is…good, actually?’ section of the book. Highly recommended: “It was not till I was in college that the idea of work finally broke free from the idea of making a living. Then the important question became not how to make money, but what to work on.”

Range: Why Generalists Triumph in a Specialized World — David Epstein

Range David Epstein

This is the perfect book-length exploration of what I was getting at in Chapter 25. Epstein all but endorses the optionality thesis: we live in an increasingly volatile and ‘wicked’ world which doesn’t conform to a neat set of rules, which makes life much riskier for narrow specialists, while conditions are perfect for curious and flexible generalists.

Range is full of catchy case studies on the rambling career paths of generalists—Vincent van Gogh, Johannes Kepler, the guy who invented GameBoy—but the difference is, it doesn’t rely on them. Instead of creating cute narratives from whole cloth, Epstein unpicks a bunch of myths perpetuated by previous airport book gurus: the 10,000 hours of deliberate practice, the Tiger Mom, the idea that you ought to relentlessly specialise from childhood.

This is an excellent book that deserves its success. You’ll probably have to skim a bunch of ideas you’ve heard before, but there’s a ton of value in the synthesis.

Marc Andreessen Career Guide

Another big inspiration. Andreessen took down his blog but you can still find archived copies of it online. I covered the main points in the book, but it’s still worth a read—there’s good stuff on managing risk through different phases in your life, and if you’re near the beginning of your career, thinking about which kind of degree/skill acquisition is likely to have the highest ROI.

So Good They Can’t Ignore You — Cal Newport

so good they can't ignore youAn artful deconstruction of the passion myth, the importance of developing mastery, and an argument for building career capital before trying to dive straight into the deep end of entrepreneurship/freelancing, or ‘lifestyle design’ more broadly. I’m also a big fan of Deep Work, and wrote a full review of Digital Minimalism here.

Early Retirement Extreme – Jacob Lund Fisker

Early Retirement Extreme coverBefore Mr Money Mustache, Jacob Fisker was the early retirement guy. The ‘extreme’ bit is not an exaggeration—Fisker lived in an RV, owned one knife, sorta thing—but the principles he outlines can be scaled to any set of preferences.

I’m pretty sure the systems framework of ERE was a big influence on Optionality, although stylistically and content-wise it’s a very different book. If you have the kind of brain that appreciates systems thinking/attacking problems like engineering challenges, then you will get a lot out of this. If not, I don’t recommend it as strongly: it has much more in common with a textbook than a typical personal finance book.

How to Fail at Almost Everything and Still Win Big — Scott Adams

how to fail coverScott has uh, kind of jumped the shark lately but this is an excellent book. His reframing of the goals problem into the more serene ‘follow your systems and see what happens’ approach has really shaped my thinking, as has the concept of the talent stack described in the book. It’s mixed with a bunch of positive affirmations-style stuff, which I am not a fan of, so it’s kind of an uneven read, but definitely still worth checking out.

Poor Charlie’s Almanack — Charlie Munger

poor charlie's almanackI am in the weird position of being a big fan of Munger (and to a lesser extent, Buffett) despite thinking the thing they’re actually famous for is overrated and un-replicable. My mixed feelings are reflected in this strange ‘book’, the first chunk of which is pure hagiography, with every man and their dog enlisted to share stories about what a great fellow Charlie Munger is. The rest is a collection of essays and speeches, many of which are available elsewhere for free, some of which are extremely specific and dated (an obscure accounting scandal from the 80s), and all of which overlap with one another.

By the end, you’ve heard all Munger’s hilarious one-liners and anecdotes several times over, to the point where it gets kind of cringe. Thankfully, the actual advice is excellent. A lot of Munger’s adages have stuck with me—he has that trick of boiling down a big concept into a memorable phrase or mental model—although I think you could probably get ~80% of the value by reading Elementary Worldy Wisdom. If this was more coherent it would be an easy five stars from me; adjust according to your tolerance for repetition and ‘aw shucks’ self-aggrandisement.

How to Take Smart Notes — Sönke Ahrens

If you want to learn more about the Zettelkasten method I discuss in Chapter 16, you can either check out my post on how I use Roam as a commonplace book, or go straight to the source with How to Take Smart Notes.

This is a terrific read because the author eats his own dogfood: the book was born of a Zettelkasten practice, and you can tell. It’s packed full of interconnected ideas, rather than the usual nonfiction gimmick where you get one central idea padded out with layers of filler and examples.

Flow — Mihaly Csikszentmihalyi

flow coverI’m looking forward to rereading Flow soon. It didn’t hit me that hard at the time, but after going through my notes and reflecting on the core ideas that went into my own book, I think this has to be my favourite positive psychology book. It draws explicit parallels with Aristotle’s concept of eudaimonia, making great points about the importance of constraints, against passive leisure, and arguing that deep work and finding ways to be present in the moment are crucial for escaping self-centred mundane concerns. Not exactly a page-turner, but highly recommended.

The Paradox of Choice — Barry Schwartz

paradox of choiceA lot of the research that the Paradox of Choice was based around has turned out to be wrong, or at the very least, not nearly as simple as was presented at the time. If you read it, be sure to see discussion here and here, as well as the criticisms I mention in the book. But it has good sections on autonomy, optimising vs ‘satisficing’, and regret minimisation which are probably still worth the price of entry, and from which I took inspiration. Schwartz was also kind enough to direct me to some of the more recent research.

Risk Savvy: How to Make Good Decisions — Gerd Gigerenzer

Remember all the popular behavioural economics research on how we’re all hopelessly biased and irrational? Gerd Gigerenzer is not a fan. He might sound like a fictional villain invented by J.K. Rowling, but he’s the real-life nemesis of Daniel Kahneman and friends.

Gigerenzer argues that our ‘fast and frugal’ heuristics are often superior for decision-making, that intuition serves us very well indeed, and that too much information makes us overconfident in conditions of uncertainty, which is one of the main points I wanted to get across in Optionality.

Risk Savvy is a solid primer on risk analysis and statistical literacy, which leads to many counterintuitive ideas, like why screening for breast or prostate cancer does more harm than good, and terrorism has such an amazing return on investment.

None of this is to say the ‘biases’ crowd are completely wrong. But it’s an important counterpoint to popular books like Thinking Fast and Slow, which definitely overstated the case.

The Optimiser’s Curse & Wrong-Way Reductions

If you’re interested in getting a better sense of the distinction between risk and uncertainty, the limitations of rationality, and the danger of overconfidence in flawed models, this is a great post. It’s written from the perspective of someone involved in the Effective Altruism community, and has a fair amount of inside-baseball stuff that might be confusing to outsiders, but it is a perfect encapsulation of my concerns with the rationalist approach to making decisions under uncertainty (Bayesian statistics), along with some useful paths forward.

Against the Gods: The Remarkable Story of Risk — Peter Bernstein

Against the Gods: The remarkable story of risk

This classic delves into the history of probability, insurance, gambling, game theory, expected value, Bayesian reasoning, options, and crowd-driven market dynamics. It’s pretty dense, but offers up all sorts of interesting gems: did you know there was huge pushback against the ‘infidel’ Hindu-Arabic counting system we use today, to the point where bankers in Florence had to disguise themselves as Muslims in order to learn the new system? Or that Francis Galton’s creepy obsession with eugenics led him to make a bunch of discoveries in statistics?

I don’t expect this book to appeal to everyone, but it’s a good introduction to some of the core concepts of risk management, and I personally found it fascinating to see how these ideas evolved.

The (Mis)Behavior of Markets – Benoit Mandelbrot

Misbehavior of Markets, Benoit Mandelbrot

Nassim Taleb’s mentor and collaborator, and clearly a huge source of inspiration for the ideas that he (Taleb) has popularised. The (Mis)Behavior of Markets is a surprisingly readable walkthrough of the flaws in modern finance theory, accompanied by plenty of diagrams and charts to help the lay reader. Good stuff on volatility clustering together, independence of price movements, ‘wild’ uncertainty, and an explanation of fractal randomness. Recommended for aspiring finance geeks.

FoundMyFitness podcast — Rhonda Patrick

found my fitness podcastI have a ton of notes on fasting, and intend to write a mega-post on this soon, because I’m struggling to find the kind of written resource that treats the subject thoroughly enough. In the meantime, Rhonda Patrick’s podcast is a pretty great place to start, as she’s both an active researcher and a science communicator. Check out the episodes with Valter Longo and Satchin Panda in particular.

Patrick also has great episodes on ageing, sauna therapy, depression, and gets deep into the weeds on various drugs, supplements, and other biochemistry stuff.

FoundMyFitness Sauna Overview — Rhonda Patrick

This is exactly the kind of written resource I’d like to see someone put together for fasting. It covers the history of sauna bathing, the strength of the current evidence for benefits, the potential mechanisms involved, the risk factors and best practice, and cites every claim throughout. A perfect explanation of why saunas are such a promising health intervention—like doing cardio while you sit on your ass—and why I’ll be installing one as soon as I have a fixed geographic location.

The Hungry Brain — Stephan Guyenet

hungry brainThis is far and away the best explanation I’ve come across for unpacking the causes of obesity, calories in calories out, low carb vs low fat, and a bunch of other long-running nutritional debates. If you’re curious about my claim in the book that it’s incredibly difficult for people to lose large amounts of weight over the longterm, this will give you a lot of the context.

The neuroscience stuff is intense, so I skimmed quite a bit. It gets digestible again towards the end, and wraps up with some simple takeaways.

Stronglifts 5×5 — Weightlifting for Beginners

There are two simple programs that are broadly considered to be the best for getting people into lifting: Stronglifts 5×5, and Mark Rippetoe’s Starting Strength. Of the two, I prefer Stronglifts, which happens to be how I cut my baby teeth 10 years ago. It’s not actually the program I would use if I was training a noob myself—it’s slow to get started, it’s not very intense, it’s missing pullups—but crucially, it’s simple, which makes all the difference when you’re navigating this confusing new world for the first time. Having an app which does all the calculations and tells you what to do also makes life that much easier.

Once you feel more comfortable and have tapped out the early gains, you can switch to an intermediate program: I highly recommend Jim Wendler’s 5/3/1, which I used variations of for several years with good results.

In terms of recommendations for learning about the mechanics of lifting, or questions about safety and best practice, the Stronglifts guide contains everything you could conceivably need to know in the early stages. If you get stuck with questions, YouTube is a goldmine, as are the relevant reddit communities—in this case, r/stronglifts5x5, with r/gainit also beginner-friendly, and then r/weightroom once you get more advanced.

Reddit Recommended Routine — Calisthenics for Beginners

I think my routine for getting started with calisthenics is pretty good, but if you want to be part of a community of people who are all doing the same thing, then the Recommended Routine (RR) from r/bodyweightfitness is the way to go. This is another unusually helpful and supportive subreddit, with detailed guides to every aspect of the routine, along with form checks, and regular discussion threads for noobs.

My nitpick with the RR is that it’s long and so cautious with warmups etc as to be boring, but at least it means you can’t really go wrong. If you get more advanced and want to learn more about the principles of programming and mechanics of each exercise, then Overcoming Gravity is the bible for body fitness. And YouTube is once again your friend here—I made a few breakthrough when I got stuck by watching the likes of Antranik and FitnessFAQs, or just searching for the specific question I had.

Invest Like the Best podcast — Patrick O’Shaughnessy

invest like the best podcastI love this podcast not only for the investing content, but also the wide range of guests: on entrepreneurship, technology, new markets, time management, media, monetary policy, mental models, and marketing, among other things. Case in point: the episode with Peter Attia on ‘healthspan’ and longevity is one of my all-time favourites. There are transcripts available for some of the newer episodes, which is a huge benefit for me, and the overall format is very tight and professional. One of my favourite recent episodes is ‘Charlie Songhurst: Lessons from Investing in 483 Companies‘.

Venture Stories by Village Global podcast — Erik Torenberg

venture storiesSimilar format to Invest Like the Best, with a loose focus on investing and entrepreneurship, but a wide-ranging selection of guests talking about their particular obsessions and areas of expertise. Some of my personal favourite episodes are Andrew Kortina, Arnold Kling, and Conor from Roam (this is probably the clearest articulation of what Roam is, and what it’s trying to do).

The Happiness Hypothesis – Jonathan Haidt

Jonathan Haidt Happiness Hypothesis

Not as good as The Righteous Mind, but still a great read. Haidt’s central metaphor is modelling the divided self as a power struggle between a powerful but largely unconscious entity (the elephant), directed with varying degrees of success by a conscious rider (the part of us that feels like us).

The main thesis, roughly paraphrased, is to align these selves to a common cause, and go with our biological imperative rather than rely too heavily on reason. This has implications for all sorts of things, up to and including morality. Where the Greeks focused on character and self-development, modern ethics focuses on particular actions: Kill one to save five? Abort a baby or not? Haidt argues the shift away from virtue was a grave mistake, because it reduces the scope of morality—we hardly ever run into these trolley-problem-style scenarios in real life. It also relies on bad psychology: “Trying to make children behave ethically by teaching them to reason well is like trying to make a dog happy by wagging its tail. It gets causality backwards.”

Honestly, there’s too much to unpack here. The book is kind of broad and meandering, but a) who am I to talk, and b) that’s a large part of why I loved it.

Waking Up: A Guide to Spirituality Without Religion — Sam Harris

waking up sam harrisNew Atheists are deathly boring but this isn’t another broadside against sky fairies etc. It’s a lay-friendly introduction to the illusion of selfhood framed through the science of consciousness, and practices for losing the sense of self/ego—mostly Vipassana-style meditation and Buddhism.

There are also some passages on LSD and mushrooms that I found interesting—Sam seems like a sober, stick-in-the-mud guy, so saying he would be disappointed if his daughters didn’t try psychedelics at least once was pretty funny.

This book is ultimately somewhat unsatisfying in terms of laying out a clear path to secular spirituality, but I do think it provides a lot of the background context required to start thinking about this in more actionable ways.

The Gervais Principle & Be Slightly Evil — Venkatesh Rao

I’m bundling these together because I think they work best as a package deal. Yes, The Gervais Principle is a sociological model built around fictional characters from a popular TV show (The Office). Yes, it feels like Rao is making shit up from the comfort of his couch: arbitrarily dividing the world into Sociopaths, Clueless, and Losers. But who cares! All models are wrong; at least this is one is entertaining and insightful.

I hadn’t even seen The Office before, but I still got a lot out of this book stitched-together series of blog posts. Rao is great at surfacing subterranean status dynamics and office politics. One section in particular gave me goosebumps: the hollowness that comes from seeing social reality as theatre, and running out of masks to paper over the void.

Be Slightly Evil probably works best for people who have already fallen down this rabbithole, and are feeling mixed-up about social reality, status games, and the process of meaning-making.

So this is a high-variance recommendation: I think Rao is not going to appeal to most of you, but for the few who who do, he will immediately become your slightly cranky spiritual adviser/uncle. I’ve ended up buying every single one of his collections, even though they’re hit-and-miss, and feel a weird sense of kinship that I don’t really feel with other writers. I’m still not entirely sure why, and your results may vary, but I had to include him as an influence.

Zero to One — Peter Thiel

zero to oneThis is required reading for entrepreneurs, but I found it useful as a regular person too. The first thesis is that competition is the enemy, and all successful businesses are effectively monopolies. I find this to be a very useful framing for finding an edge, thinking about the relative efficiency of a market, escaping from status games that are largely driven by social consensus, and ‘owning’ your own concept handle or talent stack (kind of like what I’m doing with optionality). This has a lot to do with escaping the cycle of mimetic desire, which I touched upon briefly in the book—Girard was a major influence on Thiel.

I am much less sure about the second thesis, which is about the importance of visionary planning and definite thinking about the future. But I did find it useful to encounter a strong argument against optionality, and having to process Thiel’s criticisms helped me arrive at a bunch of insights and a more nuanced view of my own argument (as detailed in Chapter 25: A Time to Improvise and a Time to Make Plans).

Principles – Ray Dalio

PrinciplesAn old PDF file of Ray Dalio’s musings has been circulating around startup circles for years, taking on a semi-mythical status. Dalio is the founder of the world’s most successful hedge fund, and Principles gives a pretty good insight as to why. I skipped over the management section, but the personal principles he’s developed over the years are great, and his frame on the risk of ruin in particular was very useful to me.

While the version I read is repetitive and a bit clunky, there’s good news: Dalio released a proper book version in 2017, with the help of an actual writer and editor, which I’m looking forward to reading (if you want the free PDF ‘draft’, it’s here).

Tropical MBA podcast

This show explores every facet of location-independent business, freelancing, start-ups, productivity, and the nomad life in general. It has loads of practical advice, and offers transcripts of most episodes, which makes it easy to go back and pull things out.

I haven’t listened to it in while, but my favourite episodes include entrepreneur and author Taylor Pearson on 90 day sprints and goalsetting, and computer scientist Cal Newport on ‘deep work’.

FIREcalc — Retirement Outcomes Calculator

This is the tool I mention in Chapter 23: Beware of Geeks Bearing Formulas. It lets you play around with your retirement funds and expenses and chart how your portfolio would have performed across every period in history. See for yourself just how ‘safe’ the safe withdrawal rate really is.

Happy Money — Elizabeth Dunn

Happy Money

Cutesy title, great book. I drew upon Dunn’s work in a couple of sections of Optionality (on debt as funny money, and experiential happiness). She summaries the research on how to spend money in order to maximise happiness, which boils down to five principles: buy experiences, make it a treat, buy time, pay now but consume later, and invest in others. These are fleshed out with amusing anecdotes and pop culture references, which makes it a fun and easy read.

The Life-Changing Magic of Tidying Up – Marie Kondo

The Life-Changing Magic of Tidying Up: Marie Kondo

Marie Kondo—queen of decluttering, bestselling author, empire-builder—hears voices in her head. They spoke to her one fateful day, as she kneeled in supplication on her bedroom floor after yet another failed attempt at tidying up:

“Look more closely at what is there.”

Most people who start hearing strange voices might take it as a sign that maybe their obsession is getting a little bit out of hand. For Kondo, it was a sign from above. This epiphany set her down the pathway to developing her famous KonMari Method™, which she has used to help thousands of clients organise their homes.

I unironically believe that Marie Kondo is a genius. Her advice is batshit crazy on the surface, but it’s like a Zen koan or something, where there’s a deeply meaningful insight beneath the banality. As I concluded in my full-length review, The Life-Changing Magic of Tidying Up is completely deranged…and I love it.

Inadequate Equilibria: Where and How Civilizations Get Stuck — Eliezer Yudkowsky

inadequate equilibriaTrying to do the impossible? Under what conditions might you expect to have an ‘edge’ over markets, domain experts, and social consensus? Unfortunately, Inadequate Equilibria doesn’t provide a satisfying answer to this question, but it does raise many excellent points in contemplating it, from which I took a bunch of notes. This is another one of those books that I think most people will bounce off hard, so I only recommend it if you want to go deeper on the EMH, game theory, and coordination problems.

Finite and Infinite Games: A Vision of Life as Play and Possibility — James Carse

finite and infinite gamesA cult classic published in 1987. I didn’t really like it at first—I felt like it just made the same point over and over again—but then I realised just how much it had influenced me when I was writing Optionality. Contrary to the whole ‘every book should be a blog post’ thing, I think there is some value in getting really immersed in one idea if it triggers some kind of mental reframing—I’ve had the same experience with books like The War of Art, which are objectively light on Actionable Content but still do something for me.

Carse’s central idea is to play the ‘infinite game’—where the goal is continuing the game, and with ever-shifting boundaries, rather than playing a finite game with the goal of winning. I saw someone accurately describe this as like ‘a Naval tweet which went on too long’, which is about right. It is short, and the first chapter is probably the best, so a cheap option to try out anyway.

Price Theory — David Friedman

price theoryA microeconomics textbook that the author has also made freely available online. I won’t claim to know how it stacks up against other textbooks, but I personally found it to be the perfect level for working through basic economic principles that I knew about, but didn’t have a strong grasp of the fundamentals.

Interesting discussions on utility and marginal value (why half-time work is better than twice as good), trade-offs (all costs are opportunity costs! this was a breakthrough for me), and game theory (why iterated prisoners dilemma still leads to defection). Friedman also gave me a definition of ‘rationality’ that actually made sense, which I borrowed in Optionality, and which I had somehow never come across in any of the screeds of rationalist material I’d read before.

Miswanting — Tim Wilson and Daniel Gilbert

An overview of the affective forecasting problem discussed in Stumbling on Happiness. I highly recommend reading the book, but this paper is short and easy to read if you’re pressed for time and just want to get the main idea.

Superforecasting: The Art and Science of Prediction – Philip Tetlock

Superforecasting - Philip Tetlock

This book sums up 20 years of research on forecasting, explaining why experts so often get it wrong, and examining a group of ‘superforecasters’—most of them ordinary people—who managed to beat the best decision-makers in a giant prediction tournament.

Unfortunately there’s not all that much to say here—making better predictions boils down to a few key points that will probably be familiar already—but it’s a well-written and pleasant read, and ties in nicely with the whole ‘non-linear uncertain world’ thesis. Should go down well if you’re a fan of Nassim Taleb or Daniel Kahneman.

Stubborn Attachments — Tyler Cowen

stubborn attachmentsProbably my favourite of Cowen’s books so far, in which he makes the case for longterm-ism and the primacy of economic growth as the central driver of human wellbeing. In classic Tyler fashion, it’s vague on specifics, but as a broad philosophical treatise it’s fascinating.

I actually disagree with him on several points—he dismisses the capabilities approach only to re-invent it in the same breath with his own vague ‘Wealth Plus’ idea, and seems to attack a strawman version of utilitarianism at one point—but I learned a lot, and included some of his ideas on hedonic adaptation, problems with happiness research, and discount rates in my own book.

If you don’t want to read it, there’s a great podcast with Rob Wiblin of 80,000 hours which gives you the main flavour.

Man’s Search for Meaning — Viktor Frankl

Quake books 4: Man's search for meaningOne of those rare books that everyone raves about for very good reason. Holocaust survivor Viktor Frankl endured unspeakable horrors in the concentration camps, and lost his brother, mother, and wife. As a trained psychiatrist, he was able to observe and treat his fellow inmates at their absolute lowest. His book is a beautiful account of finding meaning even in the most absurd and hopeless circumstances, and a defiant rejection of nihilism.

At the time, most psychologists believed all human behaviour was either an automatic response to external stimuli—as reflexive as the doctor’s hammer tapping your knee—or a conditioned response, like Pavlov’s drooling dogs.

Frankl argued that unlike other animals, we have the ability to mediate our behaviour through meaning, which allows us to find a gap between stimulus and response: “Everything can be taken from a man but one thing—the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.” ‘Find the gap’ has helped me enormously as a mantra/circuit-breaker, and I’m looking forward to a reread soon.

Money Stuff newsletter — Matt Levine

Matt is who I want to be when I grow up. His writing is accessible and witty, and breaks down the bizarre and arcane rituals of Wall Street into language that Joe Sixpack can understand. Matt is currently on paternity leave (I think?) and I noticed I have much less of a sense of what the heck is going on without his regular briefings.

I can’t point to any one specific newsletter to read, but I urge you to sign up if you’re interested in learning about finance (not personal finance, but markets, debt and equity, IPOs, regulation, securities fraud, etc). Best of all, in a world dominated by Substacks and paywalls, Money Stuff is free!

Letters From a Stoic — Seneca

Letters From a Stoic fuck-you money

Where most 2000-year-old philosophy texts are a grind, this is basically a collection of letters from your cool eccentric uncle. It might have been written yesterday, and every line is either funny, thought-provoking, or both.

I am glad to see the huge revival of interest in Stoicism in recent years, even if it’s being commercialised in a slightly icky way. I didn’t really get into it in Optionality, but I find this to be the perfect pairing with the optionality approach—it teaches you that you can control your own actions, but you can’t control your ultimate fate.

There is really nothing better than the original texts (Marcus Aurelius and Epictetus round out the holy trinity), but William Irvine’s primer A Guide to the Good Life is a great introduction if you’re not ready to dive right in.

Cognitive behavioural therapy checklists — Rob Wiblin

Freeform writing is my favourite way to work through stressful events and conflicts, but I sometimes also use CBT-style prompts to get the words flowing. Rob Wiblin shared some checklists that I find especially useful—both for overcoming career and life setbacks, and times when you feel someone has wronged you.

Sample item: “What would I say to someone else if this happened to them? Presumably not “I suggest you… feel bad 👌”.

The Algernon Argument — gwern

This is the heuristic I referenced in the ‘drugs are boring’ section. It is important to understand that there is no such thing as a free lunch, and our starting point when dabbling with performance-enhancing substances is that there will always be a trade-off somewhere. But gwern also covers possible counterexamples and ways in which we might escape this argument.

I might as well use this as a recommendation for more broadly: if you’re at all interested in nootropics, be sure to check out his detailed guides and self-experiments.

How to Change Your Mind — Michael Pollan

how to change your mindI’ve not finished reading this, but I have heard Pollan discuss the book at length on multiple podcasts, and based on that, his previous work, and multiple strong recommendations, I expect it to be the best single entry-level text on the history of psychedelic research, their safety, possible mechanisms, and applications for the likes of therapy and growth. I will update this if the book ends up disappointing me, but so far, so good.

Rationality: From AI to Zombies – Eliezer Yudkowsky

Rationality: AI to Zombies - Eliezer Yudkowsky

It took me more than six months to slog through this 2393-page monstrosity. It’s not really a book, so much as a lightly edited collection of ‘sequences’ originally posted on the Less Wrong website. I found it incredibly insightful, but I’d already tentatively worked up to it by spending the last couple of years learning about cognitive biases and the bare basics of philosophy. Even then, the bits in the middle about quantum mechanics and consciousness were way too hard for me.

I suggest checking out the author’s Harry Potter fan-fiction before you attempt this (yes, seriously). If you enjoy it, you’ll almost certainly get a lot out of his nonfiction. To be honest, I don’t really buy the central claims of the rationalist community—I prefer the Talebian version—but I do think they have some great ideas and resources, from which I have benefited enormously.

The Girard Reader — René Girard

girard readerEveryone talks about Things Hidden Since the Foundation of the World since that’s what Peter Thiel recommends (almost like…some kind of mimetic imitation?) but I think it’s not a great place to start. Instead, this reader gives you a collection of essays and interviews laying out the core ideas of mimesis and scapegoating for which Girard is best known. I loved the sections on Christ in particular, and how his sacrifice was actually meant to break the cycle of sacred violence, rather than continue to perpetuate it (guess that didn’t work out so well). Kind of repetitive at times, but easy to read/skim once you get the general idea.

Friends as Force Multipliers reading list — Sonya Mann

I mentioned in the book that I historically haven’t been all that hot on deliberately cultivating relationships and building community. My biggest inspiration here is Sonya Mann, who describes herself as a ‘writer and curious person’. I stupidly didn’t take her course, Friends as Force Multipliers, but the recommended reading list is excellent, not only for online interactions and platforms, but status dynamics more broadly. I also feel like I’ve learned a lot by just watching her and other folks like Visakan Veerasamy and Conor White-Sullivan doing their thing on twitter (both for the better, and the worse).

Impro: Improvisation and the Theatre — Keith Johnstone

This unassuming little book was published in 1979, and has since become a cult classic. It’s not really about acting, but breaking down the dynamics of status games. Johnstone, a theatre educator, explains the concepts of ‘space’, status roles, body language, and how to play higher or lower, using examples drawn from his improv practice.

The first 50 pages alone are worth the price of admission—the rest of the book is a little repetitive (pages of students’ writing exercises) and I mostly skimmed it, but it’s mercifully short anyway.

Pairs well with The Gervais Principle, and can probably be skipped if you read Kevin Simler’s essays (below).

The Status Series — Kevin Simler

Simler, who co-authored Elephant in the Brain, has also written the clearest, most plausible explanation of social status I’ve ever read. If you read his essays, you’ll see he was a big inspiration for the sections in Optionality on status games and conspicuous simplicity. I would go in this order: Social Status Down the Rabbithole, Economics of Social Status, Status as Space. There are a few other bits and pieces, including criticism from Scott Alexander and a defence, but these three are the best.

Know of other books, posts, podcasts or tools you think other Optionality readers would find interesting? The comments are open, so feel free to post your favourites below.


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