Welcome to the future, babies. It's not always going to be like this, but we can expect the highs to be higher, and the lows to be lower. Which brings us to the central premise of this book: how can we position ourselves to not only survive this kind of uncertainty, but profit from it?
In tumbling down the optionality rabbit hole, I found answers to several paradoxes I'd been struggling with: the intuition that more options are better vs so-called 'choice overload', the life-and-death importance of having both personal freedom and social constraints, and most importantly, the problem of making decisions in an increasingly uncertain world.
I also loaded up on cheap options: reading books and blogs written by weirdos, putting my own ideas out into the world, replying to thousands of emails from readers, and investing my social capital—and occasionally, cold hard cash—in friends and strangers whose talents had not yet been widely recognised.
There's no need to fret about exactly what the future holds. If you have optionality, volatility is your friend. Instead of struggling against the chaotic randomness of the universe, you can harness it to work in your favour.
What matters here is the asymmetry between the cost and the potential benefit. After all, I also have the right—but not the obligation—to go on an online shopping spree, or get McDonald's delivered to my door. I have millions of options at my fingertips at all times. The difference is that there's no positive asymmetry: the rewards are usually modest, and so are the costs. Arguably, many of these trades are asymmetrical in the wrong direction. There is such a thing as negative optionality: if you get hooked on meth or run up a gambling debt to the local mobsters, you have destroyed the right to take certain actions, and imposed an obligation in its place. So: what we're looking for is trades that offer large, unlimited upside with small, fixed costs.
Thales of Miletus was the first of the Greek philosophers. All he wanted to do was pursue his ideas, but the way Aristotle tells it, everyone made fun of him for being a nerd. “If you're so smart,” they asked, “why aren't you rich?”
The optionality approach to getting lucky starts with identifying and capping the risks which might ruin your life. This gets you into the position of 'not losing', which is a major victory in and of itself: all you have to do is consistently not-lose, and you’ll come out well ahead of the pack.
So that's my promise to you. On the defensive side, this book will get you into the position of 'not losing'. On the aggressive side, it will give you the best possible chances of hitting the big one. You can never be sure if the universe will come to the party, but optionality is the best system for making your own luck.
you can have anything you want, but you can’t have everything you want.
The only way to 'solve' an intractable problem is to reject its assumptions. Alexander the Great, faced with the impossible task of untangling the Gordian knot, pulled out his sword and chopped it in half. And so, instead of getting lost in the labyrinthine branches of the possibility tree, we can draw our pruning saws and cut them off at the trunk.
Here are some ways I have pruned my own possibility tree at various points: Banishing junk food from the house Blocking distracting websites Eating the same meals every day Refusing to own a car Not keeping up with fashions Foregoing overdrafts and credit cards
These are variations on a very old idea: that constraints can be liberating. By restricting your choices along one dimension, you can create more freedom along a dimension that’s more important to you. Almost every life philosophy—minimalism, Christianity, the Paleo diet, whatever—boils down to this kind of trade-off. Do this and not that, and you get to retire early, or lose weight, or ascend to heaven.
The single most powerful way to open up your options in life is to a) have more money, or b) require less of it in the first place. The combination of simple tastes and a healthy bank balance buys you a whole lot of freedom. This is why the second running theme of this book is the practice of frugality; smuggled in like spinach in the optionality lasagne.
When information costs more than it's worth, the rational move is to remain blissfully ignorant.
The idea is to ignore, ignore, ignore all the alluring 'deals' that are constantly dangled in our direction, then load up heavily on the rare attractive trades. This is not about self-denial: in ruthlessly pruning all the bum deals that aren't even worth considering, we're greedily optimising to get more of the things we actually want.
The biggest revelation to me was what Adeney calls the ‘shockingly simple math of early retirement’. As he pointed out, the only number that matters is the proportion of your take-home pay that you save.
As your desires become simpler, less work is required to meet your expenses, which gives you more time and freedom for other pursuits.
Systematically collecting high-quality options is the equivalent of unlocking doors that might lead to precious Treasure Chests: say, a financial windfall, a new friend or loved one, a job offer, a successful business, an excellent investment opportunity, a life-changing idea or epiphany, and all the things we generally associate with 'good luck'.
Taleb made his fortune by purchasing options that had a limited downside if they didn’t work out in his favour, but a large, open-ended upside if they did. He was happy to accumulate a lot of small, manageable losses most of the time, then make the occasional killing from rare but high-magnitude events.
If you can sell a product or service over and over again with no marginal costs—say, software, music, art, books, or digital products—you’re no longer bound by the linear returns of driving for Uber.
Reading books Most books aren’t worth reading. But the downside is capped: you can bail out as soon you realise it’s a dud, and you’ve only wasted ten bucks. This is an incredibly cheap option to take out, because every once in a while, you find a 'view quake' book which turns your whole world upside down.
Messaging strangers If you send an email introducing yourself or asking for a piece of advice from someone you admire, the worst that happens is you don’t get a reply. The potential upside is connecting with someone who might eventually become a friend or collaborator, and change the course of your life.
We live at the epicentre of this unprecedented explosion in personal freedom, abundance, and knowledge.
The point is that anyone reading this is part of the richest and most fortunate cohort that has ever existed, right back to when we crawled out of the primordial goop. Each of us has the equivalent of a personal army of invisible slaves sweating and grinding away to make our lives comfortable. The accumulated wisdom of the human race is accessible from a glass rectangle that fits in our pocket, has more computing power than the machines that put man on the Moon, and would make any ancient scholar’s eyeballs pop out of their heads, but we’re worried about whether it’s the latest glass rectangle with the dancing poop emoji.
And yet, there's nothing all that unusual about Kanye's plight. Every week some incredibly high-earning athlete, musician or businessperson is revealed to be bankrupt or heavily in debt. If they'd salted away just a small fraction of their fortune, they'd be able to live in the lap of luxury by any reasonable standard, for the rest of their lives. So why don’t they?
Economist Robin Hanson, co-author of the Elephant in the Brain, estimates that as much as 80 per cent of human behaviour boils down to signalling.
The all-consuming nature of lifestyle inflation underscores the importance of first ruthlessly min-maxing for the things that are actually worth having. If we try to maximise everything at once, we’re doomed to pound along on the hedonic treadmill forever, and end up going nowhere fast.
I can understand wanting to have millions of dollars... but once you get much beyond that, I have to tell you, it's the same hamburger. Bill Gates
Living simply doesn’t mean being some sort of miserable tightwad. My experience has been the opposite: once you have the basics of life covered, money doesn’t really correlate with happiness. The best things in life really are free, or at the very least, dirt-cheap.
Freud said the cornerstones of humanity were “love and work... work and love, that’s all there is.”
The ancient Greek conception of happiness from which Book I takes its name, Eudaimonia, is usually translated as ‘flourishing’, which encompasses not just pleasure, but purpose, and growth, and striving.
This will come as no surprise to anyone who has ever climbed a mountain, or fought for a cause, or run a marathon, or started a business, or even just opened a really stubborn pickle jar. Anything worth doing is likely to be painful, dangerous or unpleasant at least some of the time, but it provides a lot more lasting satisfaction than sitting safely in a padded room, eating candy.
We think of happiness as an outcome—reaching the shrine at the top of the mountain, where the chimera makes its lair. Instead, it’s an ongoing process
As the psychiatrist Viktor Frankl warned, you can’t pursue happiness head-on.
For example, I deliberately go several days without eating a couple of times a year. It’s not very much fun, but I believe that fasting improves my life.7 Under the naive hedonic calculus, my self-imposed ‘hardship’ is equivalent to someone who is genuinely starving, because they couldn’t afford food that week. Clearly, the ability to choose makes all the difference in the world.
The psychologist Paul Rozin observed that a single cockroach will completely wreck the appeal of a bowl of cherries, but a cherry will do nothing at all for a bowl of cockroaches. Daniel Kahneman
The principle was pithily summed up in a famous psychology paper by Roy Baumeister and colleagues, called ‘Bad is Stronger Than Good’. The implication is that rather than adding ever-more cherries to the bowl, our initial focus should be on systematically exterminating life’s cockroaches.
All you have to do is consistently not-lose, and you’ll come out well ahead of the pack. While protecting the downside always comes first, each of the four factors also opens up plenty of upside.
The first $100,000 is a bitch, but you gotta do it. I don’t care what you have to do—if it means walking everywhere and not eating anything that wasn’t purchased with a coupon, find a way to get your hands on $100,000. After that, you can ease off the gas a little bit. Charlie Munger
For now, consider the strange outcome of compounding: in each domain of life, the greatest advantages accrue to those who need them the least. This phenomenon is known as the Matthew Effect of cumulative advantage, after the conclusion to the parable of the talents in the Gospel of Matthew: “For to every one who has, more will be given, and he will have an abundance. But from the one who has not, even what he has will be taken away.”
The big guy slogging away on the treadmill is engaged in a heroic struggle worthy of Sisyphus. He has to push the boulder up the mountain every day. If he makes the smallest misstep, he slips backwards faster and faster, until he’s right back at the bottom again. Momentum is constantly working against him.
If we add a modest compounding effect to the growth curve of our financial/health/social/knowledge capital, and then add this synergistic effect on top, we get a trajectory shooting towards the sky.
At one point, it might make sense to focus on learning and acquiring skills. At another point, it might be best to accumulate cold hard cash. At another point, you might prioritise new experiences, or building social connections, or working on mental or physical health. Perhaps you notice a major liability dragging you down in one domain, or early signs of neglect that ought to be nipped in the bud. You can strategically divert effort from one bucket to another, secure in the knowledge that your overall optionality index is always on the rise.
A pair of economists are walking down the street. The younger one looks down, and spots a $20 bill on the pavement. “Hey, a twenty-dollar bill!” he says. Without so much as a glance, his older and wiser colleague replies, “Nonsense. If there was a twenty-dollar bill lying on the street, someone would have already picked it up by now.”
In financial capital: every middle-class Westerner is extravagantly wealthy, by any historical or geographical standard. We just have to be a tiny bit less profligate than our fellow bubble residents, and we can skim a big old surplus off the top.
As the computer scientist Cal Newport points out, the ability to do deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable.
This, then, is the final rule for building optionality: you have to ignore what everyone else is doing, and think carefully about what is worth competing for.
The same stunted fate befalls those who think that striving and struggling should be excised from the human condition. A life spent sitting on a mountaintop in meditative bliss is no different to floating in a vat with electrodes wired to your skull, except as a matter of aesthetics. This becomes just another way of acting dead: you'll never be more equanimous or detached from the wheel of suffering than your great-grandpa.
If you ever wished you could go back in time and do things differently, well, that’s the position you’re in right now. Every moment is an opportunity to change the future. You just have to cultivate the very unnatural tendency of being kind to some strange old geezer who shares the same name as you.
It's impossible to know exactly what your future self will want, but you can predict with near 100 per cent certainty they’ll be grateful you’ve set them up with high-quality options: financial capital, good health, valuable relationships, and useful skills and experiences. With broad capabilities and resources at their disposal, they can execute on whatever makes sense at any given moment.
We’ll get into the opportune timing for 'exploring' and 'exploiting' in Book V.
The optionality approach to planning is summarised in the popular aphorism 'better to be vaguely right than exactly wrong’.
Having a rigid budget is another example of Emerson’s foolish consistency. It’s like catching a bus that takes you further away from your desired destination, just because you already bought a ticket.
Buying a gigantic blocky cellphone was a power move for the swinging dicks of Wall Street in the 80s; nowadays the homeless guy on the corner has a better model.
We can choose between thousands of different types of breakfast cereal. But why eat cereal? Maybe simple carbs aren't the best way to start the day. It took me a long time to discover that I not only perform better when I fast in the morning, but the ‘breakfast is the most important meal of the day!’ thing was literally a marketing slogan invented by one Dr Kellogg.
Consumer capitalism creates the illusion of great choice, but the branches of the possibility tree are almost all minor variations on the same core theme. This is Faux Optionality: an overwhelming array designed to keep us confined in one narrow sector of possibility-space, and obscure the decisions that actually matter.
I’ve quit smoking, don't have drug problems, rarely consume media mindlessly, keep myself in good shape, only own things that bring me joy, and carefully steward my finances. It’s always a work-in-progress, but I generally feel like I’m in control of my life.
In a low state of physiological ‘arousal’, we underestimate how much our desires will change when our blood is running hot. When I tell myself I'm going to have a quiet night, I am quite certain of this fact, and cannot be moved from it. Next thing I know, it's 3am, my wallet is empty, and I have half a kebab smeared over my face.
I don’t keep ice cream or other junk food in the house, because experience has taught me I'll eat the whole carton in one sitting.
This is what Thaler and Sunstein call changing your ‘choice architecture’—redesigning the way in which options are presented to you.
Other examples include removing your email address from promotional lists, using ad blockers online, deleting distracting apps, not watching the news, and generally muffling the Siren song wherever you can. It’s not necessarily going to save you from temptation, but it’s a good start.
I could still gorge myself on ice cream whenever I want, but I’d have to put pants on, leave my apartment, and walk to the 7-Eleven. That trivial inconvenience is almost always enough to put me off.
The idea of a trivial inconvenience is to deliberately add some friction back into the process.
The classic trick is freezing your credit card in a block of ice, forcing you to wait several hours for it to thaw before you can use it.
The set-and-forget approach is perhaps the most powerful financial strategy for effortlessly making better temporal trade-offs, to the point where I strongly recommend nudging yourself in at least one of the following ways:
We can abuse our bodies for decades and accumulate all sorts of silent risk before it finally catches up with us.
The great thing about nudges is they take the very natural inclination to sit on one’s ass, and turn it into a strength.
Once you sign yourself up for a monthly savings plan, or cancel an ongoing subscription, you never have to give it another moment’s thought. If you've got the right systems in place, kicking back and doing nothing isn’t just a good strategy—it’s the best strategy.
I’ve already suggested two keystone contenders in the realm of finance: tracking net worth, and expense ratio. The mere act of writing this stuff down day after day is often enough to change your behaviour.
Psychologist and self-help author Jordan Peterson’s mantra is ‘clean your room’. The idea is that you get some easy wins on the board, and build up confidence.
Probably you’ve read articles about how Obama wears the same suit every day, or Mark Zuckerberg has seventeen identical grey t-shirts in his wardrobe. The idea is to deliberately eliminate inconsequential daily choices and free up mental bandwidth for more important decisions; like ordering drone strikes or strip-mining billions of people’s information to sell to advertisers.
Experience has taught me that striving for perfection is a recipe for eternal dissatisfaction and self-flagellation. It's much better to get to the point of ‘good enough’, and leave it at that.
Domains that are good candidates for automation have two defining features: they don't benefit from variety (habituation is the whole point) and they're stable over time—there's no benefit to constant tinkering and exploration.
The same goes for things like work habits, writing, appearance, exercise, and all of the bodily functions. In these domains, it's better to experiment just enough to find what works for you, then become a creature of habit at the earliest possible opportunity.
Men, it has been well said, think in herds; it will be seen that they go mad in herds, while they only recover their senses slowly, and one by one.
It's almost always a bad idea to give well-meaning advice to the people around you, unless they ask for it—and even then, tread carefully. Instead, all you can do is shut up and live your best life. If the results are compelling enough, people will get curious, and voluntarily start rewriting their own stories.
The second rule of thumb is that when there are no consequences for being wrong, or there is no ‘wrong’, don’t be embarrassed to follow the crowd. The reason we dance in unison, or sing together, or march in line, or wear uniform-like fashions, or swap in-jokes and memes, is that it feels pretty great to be a part of the hivemind.
In the domains of sports and aesthetics, it makes perfect sense to indulge in some (mostly) harmless tribalism. Who cares which team is ‘actually’ better, or whether Game of Thrones is any good? These are arbitrary focal points for bonding with your fellow apes, and satisfying that impulse to be one with the group. You get some water cooler chat, you feel closer to the people around you, and you build social capital. Go, uh, Wildcats!
The second rule for contrarianism is summarised by G. K. Chesterton: "A man must be orthodox upon most things, or he will never even have time to preach his own heresy." Building social capital makes it that much easier to gracefully bow out of bad signalling games. Whenever your health, wealth, or autonomy are on the line, that’s the time to be an uncompromising weirdo.
Book ii could be summarised by the Yiddish proverb ‘der mentsh trakht un got lakht’: man plans, and God laughs. Even if we formulate and execute upon a goal perfectly, we still don’t have control over the outcome. There's an inescapable element of randomness: we can train like a maniac, play our heart out, and still lose to a better opponent, or be derailed by a stroke of bad luck.
As Scott Adams points out, every single day that you follow your systems, you’re a winner. You’re focused on the things within your control. If you want to be an athlete, as long as you train your heart out, it doesn’t matter if you lose a game. If you want to be a writer, all you can do is get up at 5am every morning and pay your dues. So long as your overall optionality index is on the rise—building relationships, net worth, health, or skills—it doesn’t matter if you miss any arbitrary milestone.
The defining feature of modernity is that we’re being pushed towards short-term hedonism, at the expense of long-term flourishing. Our feedback loops are hopelessly laggy, and we have to tighten them up.
Sometimes there’s no feedback loop at all: we accumulate silent risk over the years with no outward sign of danger, then we’re struck down seemingly overnight.
We don’t get slimmer after going for one run, or get rich after making one savvy spending decision. We have to keep doing it over and over again before we notice any results. Sometimes there’s no feedback loop at all: we grind away for years with no outward sign of success, then it all happens seemingly overnight.
We’re definitely going to lose sometimes: either through our own weakness of will, or because God dealt us a shitty hand. Whatever happens, we shrug our shoulders, and go back to the daily practice.
The stunning result turned the research on addiction upside down. Did the soldiers suddenly grow bulging willpower muscles on the plane home? Were they injected with moral fibre? Did they carefully visualise their goals, or use the three-step habit trick? Of course not. This was the first major piece of evidence to suggest that choice architecture is vastly more important than self-control.
Civilisation has done a remarkable job of reining in our animalistic drives, and rechanneling them toward productive ends. There’s plenty more work to be done, but we didn’t get this far by wishing away human nature.
Knowing is not enough; we must apply. Willing is not enough; we must do. Johann Wolfgang von Goethe
If I'm honest, much of my distaste for clutter is on aesthetic grounds—which is to say, personal preference.
If you believe the environmental psychologists, being surrounded by stuff literally makes it harder to think clearly—all that visual clutter makes for a messy mind. In light of all of this, we might reconsider the relationship between people and possessions: who owns who, exactly?
In his textbook Early Retirement Extreme, the Danish astrophysicist Jacob Fisker points to another transformative technology: online secondhand markets. Most people don't appreciate that you can not only buy stuff dirt-cheap online, you can also store your stuff for free. Think of eBay and Craigslist as enormous virtual storage warehouses, filled with millions of items you can borrow for next to nothing. When you need something, buy it secondhand. When you’re done with it, flick it off again. Chances are you’ll recover most of the price you paid, and if you understand the basics of writing ad copy, you might even come out in the black.
These decisions are easily reversible. If you flick off a generic item that you end up needing again, you’ll always be able to find it for sale. This means that technically, the only items you have to own outright are those that are unique, or have sentimental value.
If everyone followed even the weakest version of this heuristic—say, passing on generic items after five years of collecting dust—acres of self-storage units would be liberated overnight.
Imagine buying a cheap plastic laptop designed for children that can’t open more than a dozen tabs without bricking itself. Now imagine you’re a writer, and this hunk o’ junk is the primary tool you use for several hours each and every day. Imagine how dumb you’d have to be to endure that much frustration and wasted time for the sake of a couple hundred bucks. I don’t have to imagine, because I was that guy. After hitting peak pathological penny-pinching circa 2016, I've learned which things are worth paying money for. Sometimes, a lot of money.
It’s true that min-maxing requires us to cut out a mountain of crap, but only so we can greedily load up on the things that bring us joy. I don't see any reason to arbitrarily exclude 'material possessions' from this latter category. Personally, I want to have more cool stuff, not less, and I'm increasingly willing to pay top dollar for it.
Buy the very best-in-class for a small set of items, buy the cheapest possible version of everything else, and avoid the middle ground.
This last one presents us with another juicy asymmetry. Most people borrow their desires from others, which makes it hard to have a truly unique experience. There is much option value in exploring the under-explored, and little-to-none in taking the path well-travelled.
If you skip the top-tier or ‘must-do’ attraction, you will usually have a much better time at a fraction of the price.
I wonder if we’re trapped in an Emperor’s New Clothes situation, where everyone is secretly underwhelmed, but no-one wants to defect from the agreed-upon narrative. Instead, we post up our happy snaps and loudly reassure each other how great it was.
The Matthew effect suggests popular things often become popular through what amounts to good luck, with an early breakthrough launched into the stratosphere by social contagion. Our opinions and preferences cluster together, but it's not as if we’ve carefully evaluated the options on their merits and all come to the same conclusion. We just want to feel close to our fellow apes.
The only explanation that fits is the most awkward one. We don’t really want to see the Mona Lisa. We want to be seen seeing the Mona Lisa.
'Health' isn't defined by the presence of anything in particular, but by the absence of problems: if you don't have diseases, aches, pains, visible deformities, or clogged arteries, well, that's about the best you could hope for.
As any 5-year-old child could tell you, death is bad. As adults, we successfully fool ourselves with elaborate rationalisations about its 'deeper meaning', which is a strong contender for the most absurd case of sour grapes in the history of the universe.
Personally, I eat some kind of junk food pretty much every day, rarely do more than three hours of exercise a week, and haven't counted calories in years. But I've never been fitter! I would love to attribute this to some moral superiority on my part—something something 'perspiration beats inspiration'—but the truth is that I am lazy, and incapable of forcing myself to do anything I don't want to. I say this not as an elaborate humblebrag, but to draw attention to two criminally neglected points: 1. Everything compounds 2. Heavy resistance training has a much higher return on investment than cardio Lifting weights is proof that God very occasionally hides cheat codes in our simulation: just press START, then button mash up/down/up/down. If you can build up a little strength and muscle mass, you kickstart a positive feedback loop which makes life easier on every possible dimension. Let us count the ways:
What about cardio? Resistance training throws in a basic level of cardiovascular fitness as a freebie, but we also want to pair the intense stuff up with its polar opposite: large volumes of slow and unstrenuous movement, so gentle that it barely qualifies as exercise.
This gives us the barbell strategy for barbells: short bursts of intense effort on the hyper-aggressive ‘expensive’ end, and lots of low-effort movement on the hyper-conservative ‘cheap’ end
The distribution is highly asymmetrical, so we might aim for 2.5 hours of intense exercise each week, but 25 hours of gentle movement.
The best way to rack up a ton of low-intensity movement is to make it part of your daily life. You shouldn’t have to put on any special clothing or think of it as ‘working out’.
A simple version of this strategy is to get in the habit of walking everywhere. Strolling appears to have some kind of magic juju, perhaps because humans are built to walk long distances: everyone from Nietzsche to Thoreau has raved about the powers of perambulation, and many a creative breakthrough has been attributed to a long rambling walk.
The integrated-lifestyle approach beats dedicated cardio on two fronts. First, we need lots of movement spaced throughout the day, and there's no way to 'catch up' on it with one big dose: pounding the treadmill does not compensate for 10 hours slouched over a computer. It's also more pleasant: in following the barbell strategy, I've managed to get my V02 max and resting heart rate (the best measures of cardiovascular health) in the 'good' to 'very good' range without doing a lick of deliberate cardio.
The middle ground of the barbell represents moderate-intensity exercise which you have to go out of your way to perform: jogging, treadmills, cross-trainers, serious Lycra-clad cycling. This category also includes such abominations as random circuit training and the Patrick Bateman stomach-crunch routine, which blend cardio and strength into a slurry of mediocrity. These exercises don’t burn many calories, don’t build much lean mass, are time-consuming, require deliberate effort, and can interfere with recovery.
Nevertheless, I chose to go cold turkey when I quit smoking: not only because vape pens are the fedora of the mouth, but because the upside of nicotine is just not that exciting.
The central argument of this book is that volatility requires us to explore more: our preferences aren't stable over time, and neither are the activities the world rewards us for. But this is not true of stable domains like human physiology. There are some occasional variations—the mutation that gave my ancestors the ability to digest milk only spread 4000 years ago—but the pace of change is extraordinarily slow.
I started out vaguely exercising, dabbled in powerlifting, moved to calisthenics, and ended up with a hybrid model. Now I’m done.
Lindy leads us towards practices and technologies with the longest continuous history, and cautions us with the corollary: the more recent an intervention is, the more likely it is to be a fad, a scam, or a boring 'fiddling on the margins' Dead End that distracts us from the things that actually matter.
It is very dangerous to not lift weights. Resistance training is massively protective against the risk of ruin, and creates a positive feedback loop that acts as a force multiplier in every area of life. This is best paired up with lots of low-level movement integrated into daily life. If you follow the barbell strategy for exercise, you never have to run another day in your life. Health capital is an unusually stable domain. Experiment long enough to find out what works for you, then become a creature of habit at the earliest opportunity.
The third myth I fell for was the social norm that relationships should either happen naturally, or not at all. It’s cold and calculating to 'curate' the people in our lives, and strategically cultivating new connections is downright creepy.
The final myth I swallowed is that if we succeed in this unnatural endeavour, we risk ending up surrounded by like-minded people. This, too, is shameful: it's anti-egalitarian to live in a 'bubble' that doesn't reflect broader society.
The taboo at the heart of all four myths is a belief that social capital has been handed down by God in his heaven, and it's wrong to strategically accumulate or allocate it. It might be OK if you change your social position by accident, as a consequence of something else, but it mustn't be pursued as a goal in and of itself. This is the single most limiting set of beliefs I have ever personally had to overcome. No-one in their right minds would think that financial capital accumulates effortlessly, or knowledge, or health. You can improve anything when you a) learn how it works and b) apply targeted effort, and it should have been obvious to me that relationships are not some magical exception.
Once again, we've somehow managed to backslide from the more sophisticated understanding of the ancient Greeks: to truly love someone is to help them grow, to teach and be taught, to avoid stagnation and ruin.
I like Kevin Simler's definition of friendship as a pact in which two people agree to dispense with all the usual fine-grained accounting of status transactions. That way you can play freely—including taking the piss out of yourself and each other—purely for fun, with nothing at stake.
Old friends and family are an especially good investment because they are non-fungible: you have built up a store of shared history, in-jokes, and mutual understanding that cannot be transferred to any other soul.
Up-and-coming artists or students or entrepreneurs don't have armies of fans and backers behind them. Quite possibly, they are hanging on by a thread. A few well-placed words of praise and encouragement can change everything.
The economist Tyler Cowen encouraged his most talented students to skip a Masters degree and go straight for the PhD. They often didn't believe they were capable of making the leap, or realise this was even possible. Cowen suggests that raising the aspirations of other people in these critical moments is one of the most valuable things you can do with your life: "It costs you relatively little to do this, but the benefit to them, and to the broader world, may be enormous."
When passionate and like-minded people congregate in one place, the whole becomes much more than the sum of its parts. Contrary to the myth of the lone genius, many of the greatest achievements in history arose out of a scene of people riffing on each other's work, contributing new ideas, and supporting one another—what musician Brian Eno calls a scenius. Think the Bloomsbury Group, Florence during the Renaissance, Paris in the 1920s, the innovation hothouse of Xerox Parc, or parts of Silicon Valley today.
A scenius is a beautiful bubble that only forms under special conditions: friendly competition and appreciation, rapid exchange of new ideas, mutual sharing of success, and most importantly, a buffer against the outside world that creates space for transgression and general weirdness.
Once you've found the spaces and groups most likely to select for the kind of people you want to meet, it becomes a pure numbers game. If you don't put yourself out there, your chances will always and forever be zero. Some people are preternaturally bad at taking advantage of this obvious asymmetry, and I should know: every single time I have to go out and meet new people, I bitterly curse my former self for ever agreeing to it. This is despite the fact that 95 per cent of the time I come home having had fun, and very occasionally meet someone who changes my life.
The blog expands my surface area for serendipity far beyond what I could achieve in real life. It's like permanently being at a party, meeting interesting people from all around the world.
A friend suggested that blogs are part of our extended phenotype, and the image of a digital peacock's tail that suggestively swooshes through cyberspace has stuck in my mind. Incredibly, it works. People write to me to share their triumphs and woes, to swap recommendations, to challenge my thinking, and to invite me into their homes for fine seafood dinners. I’ve met some of my closest confidants and friends as a direct result of blogging. My girlfriend was an early Deep Dish reader. So were several of the folks who helped me put together this book.
While I was lucky to have a couple of early posts go viral, the modal outcome of blogging is that you pour your heart out and get nothing but crickets in return. It takes a long time and lot of effort to build a following, which means any social capital should really be viewed as a happy byproduct of the main goal (for me, enforced writing practice and figuring out what I think).
Every new technology generates its own moral panic: TV emits alpha waves that rot our brains, video games encourage violence, social media destroys our attention spans, news media is only making us dumber; fidget spinners are probably the equivalent of black-tar heroin. It would be a stretch to describe any of these passive leisure activities as Bottomless Pits of Doom. They might be dangerous, but only insofar as they're dead ends that lead us away from valuable options. As with anything in the sticky middle, the real cost is the missed opportunity.
Netflix's confirmation that its real competitor is 'sleep' has to be the closest a company has come to an outright admission of evil. But the biggest loser by far is knowledge capital—the sum total of all of our skills, qualifications, ideas, and understanding of the world. Building knowledge capital is a form of active leisure. What if we could repurpose even a small fraction of that great ocean of passivity towards learning stuff?
This is the 100,000 hour opportunity. In the space of a lifetime, we might become an accomplished pianist, and a chess Grandmaster, and a competitive athlete, and proficient in a second or third language, and an amateur chef, and a published poet, and a knitting maven, and a skilled programmer, and an expert in non-violent communication, and a community leader. Or we could watch a whole lot of TV.
There is a great opportunity here that arises from the confluence of three unprecedented events: more information is freely available than at any other point in history, we have more leisure time at our disposal than ever, and accumulating broad skills and knowledge has never been so valuable.
Scott Adams, creator of the Dilbert comic strip, describes himself as “a rich and famous cartoonist who doesn’t draw well”. By his own admission, his artistic skills are middling, and at social gatherings, he’s rarely the funniest person in the room. Instead, the resources at Adams' disposal were an MBA, years of experience as an office drone, an early interest in Internet culture, and a decent sense of humour. The number of aspiring cartoonists in the centre of this unlikely Venn diagram was exactly one: “If you think extraordinary talent and a maniacal pursuit of excellence are necessary for success, I say that’s just one approach, and probably the hardest. When it comes to skills, quantity often beats quality.”
As investing legend Charlie Munger observes, most of us are never going to become pro tennis players or chess grandmasters. But we can still succeed by expanding our circle of competence, and working hard to develop an "unassailable edge”.
Which brings us to the mathematical case in favour of being a generalist. You’ve heard of the Pareto Principle, or 80/20 rule: twenty per cent of your customers are responsible for 80 per cent of your profits, and so on. While this is not actually a rule, the general idea is that in any domain governed by power laws, a small number of inputs are responsible for a large proportion of the value captured
If you follow these efficient pathways, you only have to invest 20 per cent of your effort into any given field to capture most of the value. The implication is that it takes about the same amount of time and effort to truly master one skill as it does to become competent in five domains.
Some obvious talent stack contenders include writing, time management, public speaking, sales and marketing, accounting, statistics, programming, and design, all of which can fuse with just about any core trade to give you an unassailable edge.
Some of these skills might be planned and acquired strategically from the top down, but they can also emerge bottom-up out of your interests and inclinations—which has the great advantage of being intrinsically motivating.
In the case of a talent stack, the ideal is to forge a career that intersects with one or more of your hobbies, and make the notion of work-life balance obsolete.
Once you start this process, you can't stop: the danger of reading Ayn Rand or Karl Marx as an impressionable teen is that your foundations might begin to calcify. From this point on, the only answer is sustained creative destruction.
To anyone in possession of a library card or an Internet connection, the transformative upside of reading books is available for the low, low price of zero dollars. Even if you buy books—which you should, for reasons that will become clear—the return on investment is off the charts. I guess I have spent maybe $2000 on books so far, which has enriched me at least 100x over, and probably closer to three orders of magnitude.
The opportunity here is vast and unprecedented, but few people take advantage of it. The typical American finishes four books a year, allocating less than 1 per cent of their leisure time to reading. Lots of people haven't read a single book since high school. What gives?
The asymmetry of reading only remains juicy if we treat books like the cheap options they are.
One of my most interesting side projects in recent years has been helping out with the aforementioned Roam Research; a startup which has attracted a cult following in this field. Roam is deliberately structured as a psychedelic beaver dam: a knowledge graph of unique block-level ideas that can be endless remixed in new contexts, with bidirectional hyperlinks and references that make it effortless to draw connections between them.
As Nassim Taleb observes, corporations love nothing more than a family man with a million dollar mortgage to service, because he has little choice but to be an obedient servant.
Debt is negative optionality. It removes the right to take certain actions, and imposes an obligation in its place. So why are we so awash in the stuff?
Give me a lever long enough and a fulcrum on which to place it, and I shall move the world. Archimedes
Put simply, debt is borrowing money for consumption, and leverage is borrowing money to invest. Many businesses fund their operations through debt; not because they’re financially irresponsible, but because they expect to earn an outsized return on the loan. In taking someone else’s money, they can lever themselves into a more advantageous position than they would have been able to reach with their own resources.
A college degree is a glorified test of IQ and conscientiousness: the knowledge acquired is secondary, especially in non-technical degrees, and could be learned through textbooks, free online courses, and self-directed study.
“You wasted $150,000 on an education you coulda got for a buck fifty in late charges at the public library.”
It is a truth universally acknowledged that a person in possession of a good income must be in want of a house. Another truth universally acknowledged is that houses are frickin’ expensive.
“You’re going to put everything into a single, highly illiquid investment. It takes weeks or months to buy and sell, and there are eye-watering transaction costs each time. The asset is constantly deteriorating, so you’ll also need to pay a whole raft of ongoing costs, in the form of rates, insurance, and maintenance. Oh, and you’ll be up to your eyeballs in debt for decades. Questions?”
and extend the kitchen, and get a dog with urine so acidic that large patches of the lawn will never recover.
It’s almost certainly better to stay lightweight and nimble, and build some optionality.
Charlie Munger says: “All I want to know is where I'm going to die, so I'll never go there.”
This is not a new problem. The economist Frank Knight formalised the distinction between risk and uncertainty in his PhD thesis more than 100 years ago, with the key difference being that risk can be quantified and measured, while true uncertainty cannot.2
Losing feels worse than winning feels good.
In the Gospel of Matthew, Christ tells the story of a man who entrusted his fortune to three servants while he went on a long journey, dividing it up according to their ability. The first received five talents, the second two, and the third, just one. Upon the master’s return, he found the first and second servants had doubled their talents through savvy investments, and rewarded them handsomely. But the third servant, out of fear, had buried his single talent in the ground. The master cast this wretch into the pits of hell, taking his only talent and giving it to the servant who already had 10. The Matthew effect takes its name from the conclusion of the parable: “For to every one who has will more be given, and he will have an abundance; but from him who has not, even what he has will be taken away.”
As Isaac Newton put it, after losing a fortune in the South Seas stock bubble: “I can calculate the movement of stars, but not the madness of men.”
So begins a famous Paul Graham essay on the rewards of entrepreneurship. This was probably true at one point in time—Microsoft minted more than 10,000 millionaires among early employees—but these days it looks more like a marketing ploy to encourage young people to exchange their labour for false hope.
The advice to 'invest in yourself first' is as eye-rollingly banal as it is reliably underrated. This is the biggest asymmetric edge anyone has, because no-one knows you better than you do: your skills, inclinations, and character are sure as hell not priced in by the EMH, and neither are the hyper-local opportunities that you might be able to exploit.
This is a bastardisation of the barbell Taleb describes, hence the name. Personally, I'm not worried about the fact that my index funds are in the black swan danger zone. I own a stake in almost every publicly traded company in existence. The only way my portfolio could get wiped out would be an event that destroyed every single business on Earth, by which point the flesh bubbling off my charred skeleton would probably take my mind off any financial troubles.
One of Mandelbrot’s PhD students, Eugene Fama of EMH fame, wrote his thesis on this phenomenon. Fama found that price movements of more than five deviations from the average happened 2000x more often than the standard models would predict.
Live frugally Pour all your savings into low-cost passive index funds Don’t trade in and out, or try to time the market Retire once you accumulate 25x your annual expenses in investments Safely withdraw 4 per cent of your portfolio each year without running out of money
There is no world in which potato chips will suddenly start being healthy, or resistance training will become obsolete.
and the Nobel Prize-winning economist and New York Times columnist Paul Krugman infamously predicted that “by 2005 or so, it will become clear that the Internet’s impact on the economy has been no greater than the fax machine”.
Like it or not, we’re all ‘entrepreneurs’ now, even if we never start a company. The old model of stable employment for life with a government pension in retirement is no longer a safe bet. Instead, we have to increasingly think in terms of non-linear returns, protecting the downside, finding ways to profit from volatility, and creating diverse income streams.
Peter Thiel’s argument is somewhat undermined by the fact that when he co-founded PayPal, it was with modest ambitions to beam IOUs between PalmPilots and other early handheld devices. The company pivoted not once, not twice, but six times, before stumbling into a viable business idea. And even this happened almost by accident: one of the cofounders posted up a demo for online payments, triggering a deluge of emails (which he initially ignored). That idea turned out to be worth many billions of dollars, but it was never part of the plan.
In fact, Musk hasn’t had a formal business plan since 1995, when he launched his first company: “These things are just always wrong, so I didn’t bother with business plans after that.”
The graduates go on to shill their own e-books and courses to the next influx of wantrepreneurs, in a pyramid scheme so industrious that Ramses II is sitting up in his sarcophagus.
Both groups of people receive the same answer: Have a well-paying job Seriously pursue your art for love, not money
According to Bogie, the only good reason for making money was “so you can tell any son-of-a-bitch in the world to go to hell”.
There are two ways to be free: you can either get more money, or require less of it. The first is obvious, but the second doesn’t get enough love. Let's call it ‘fuck-you frugality’.
This is the same reason the Stoic philosopher Seneca used to deliberately practice poverty, despite being the richest man in Rome. Every now and then, he’d spend a few days sleeping on the floor, eating bread and water, and travelling roughly. The idea was that should his fortunes ever change, he would accept his fate without complaint or compromise:
We petty mortals can only tiptoe between the legs of history’s demigods, but at least we can tiptoe in the right direction. As a trivial example, I have deliberately maintained creative control over every detail of this book—from the title, the illustrations, the cover, the structure, right down to the typefaces. I’m not reliant on income from book sales, or trying to placate a publisher, or sexing it up with marketing sizzle in the usual manner of self-help books. Whatever will be, will be. I would much rather fail on my own terms than succeed on someone else’s.
The unspoken rule is that if you deliver the goods and aren’t an asshole, you can do what you want. I’m hardly claiming I was indispensable, but I was valuable enough to leverage some pay rises and get my own column and generally have a reasonable degree of autonomy over my work.
- Fuck-you money Stash enough cash to cover your expenses for a year or two, so you can walk away from a bad situation, find a better job, or retrain. 2. Fuck-you frugality Follow Ben Franklin’s lead, and commit to living simply rather than betray your principles. 3. Fuck-you career capital Become such a useful and profitable employee—ideally, the only person who knows how to do some important thing—that you’re difficult to push around.
Freedom is the power to choose our own chains. Jean-Jacques Rousseau
Here are some archetypes: The Peter Pan man-child who refuses to grow up The Trustafarian rich kid aimlessly wandering the earth The attractive New Yorker who constantly dates, but never settles The dilettante who flits from job to job without acquiring mastery The early retiree who triumphantly quits her job, then falls into a depressive funk
Constraints can be liberating. When you're doing creative work, the total space of all possibilities is so vast that it’s unworkable. You have to carve off one tiny little sector, and think inside the box. The same is true when you zoom out to the scale of an entire life, but this is not obvious until all the constraints are removed: you don’t know what you’ve got till it’s gone.
turns out that offices and 9 to 5s probably exist for a good reason. But while Chesterton’s fence is a useful constraint, it’s not a catch-all argument for longstanding institutions and cultural practices. The lumpy clay of human civilisation has generations of distilled wisdom baked into it; also, generations of deeply ingrained stupidity. All Chesterton was saying is that before you tear something down, you better make sure you know why it was put there in the first place.
Our individualistic mythology elevates the iconoclasts and free-wheeling mavericks who march to the beat of their own drum. But did you know that a lone wolf—far from living a noble and wild existence—has to eat rats and scavenge rotting carcasses to survive? Well, humans are social animals, too. We need hierarchy, and routine, and structure.
“Love and work… work and love, that's all there is.”
One of the stranger arcs of my adult life is that I apparently love work now. I just checked my records, and I’ve spent more than 1500 hours researching and writing this book, for example.
Today’s rich Americans can afford vastly more leisure than ever before, but as Thompson points out, they’re using their wealth “to buy the strangest of prizes: more work”. This trend only starts to make sense against the backdrop of the waning of the commons. In a world absent God or meaning, work is evolving from a means of material production to what Thompson calls a means of identity production. We’ve gone from ‘jobs’ to ‘careers’ to ‘callings’, mirroring the ascending needs of survival, status, and meaning.
But we need to be running to something, not just from something. Having a void in your life in which you wake up every morning with no structure and no obligations and a yawning chasm of time... that's the Bad Thing.
“Since retiring myself I have built two houses from the ground up, renovated a dozen other ones, raised my boy to age seven, started a blog, volunteered on loads of projects, and learned more things and had more fun than I had in the entire time I was working. It's busy, but very satisfying work.”
We need the right level of stress—not too much, not too little—to continue to grow and develop. Everyone who is not busy being born is busy dying, and all that.
The technical name is eustress. In its biochemical/physical form, we call it hormesis: micro-tears to muscle fibres make them grow back stronger; periodic fasting resets metabolic systems and cleans up damaged cells.
Impact Convincing people to hand over money for something you produce is a reasonable proxy for the value you’re creating in the world.
Fasting is categorically different to starving Signing an employment contract with the security of a fuck-you independence stack is categorically different to having to do someone's bidding to survive Eating the same meals or wearing the same clothes every day is categorically different to being forced to follow a diet or wear a uniform Starting a family is categorically different to being born into one which you did not choose Joining a religion is categorically different to being trapped in a faith which punishes apostates with death or ostracism Frugality is categorically different to not having the means to spend money in the first place
With that being said, I suspect that some of the best constraints to consider are those with a strong historical precedent: family, work, marriage, membership of clubs and groups, schedules and routines, religion, children.
‘Sink your ships behind you’ is the nuclear version of a Ulysses contract: in the context of akrasia, tying yourself to the mast was about limiting access to the self-stimulating and status-seeking products of consumer capitalism. The difference here is we’re using it to destroy genuinely valuable options.
Family and children Religion Work or entrepreneurship Philanthropy Creation (art, music, literature)
What follows is the juiciest class of options we've encountered yet. You have the right, but not the obligation, to achieve some truly extraordinary outcomes, and put your own little dent in the universe.
If we choose to play certain games, we can simultaneously improve the lives of others, have a positive impact on the planet, and make our own lives better, too. This is the art of selfish selflessness.
In justifying their own life decisions, these strident non-parents often make the argument that having children is an inherently selfish act. And they're right! Having kids is the archetypal example of selfish selflessness: it's a fundamentally self-centred decision that just so happens to make the world a much better place.
As for concerns around overpopulation, historically, these fears have been completely backwards. Every time, it's education, technology and innovation that lifts us out of poverty and saves us from imminent apocalypse, while population controls and 'de-growth' initiatives lead to stomach-churning atrocities.
Having kids is a time-honoured solution to the problem of meaning-making. If you start getting anxious about your impact on the world, or lying awake at night wondering what it's all about, you throw out a hospital pass to the next generation. Now it's someone else's problem!
Mosquitoes kill more humans than any other animal on the planet, by an enormous margin. Malaria alone infects 400 million people a year, and claims half a million lives.
This is exciting, but it raises some gnarly moral questions. If it only costs $3400 to save a life, and the opportunity has never been more compelling, wouldn't it be outrageously negligent to spend money on luxuries? If you take an expensive vacation, does that mean you've chosen to let someone die? This is the disturbing idea at the heart of moral philosopher Peter Singer's ‘drowning child' thought experiment. You're walking through the park on your way to a meeting, when you see a figure splashing in the muddy duck pond. You realise it's a child, and they're not swimming—they're drowning. You look around, but no-one else is in sight. You're wearing an expensive suit and patent-leather shoes, which will surely be spoiled. And if you miss your meeting, you'll lose out on a new client. What do you do? The overwhelming moral instinct is that it would be monstrous to walk away. So you jump in, save the child, and take the financial hit.
Unlike wealth, or health, or learning, status is purely positional. The size of the pie is fixed, and everyone's out to get a slice of it.
As our environment changes, so do our fitness indicators. Today, being slim is considered higher-status, because it's a reliable signal of conscientiousness, free time to work out, being able to afford cocaine, etc.
Another head-scratcher: my Victorian forebears poisoned themselves with lead makeup in the pursuit of whiteness, to signal that they didn't work in the sun with the peasants. Now I poison myself with radiation in the pursuit of a tan, to signal that I have the leisure time to escape the office and lie around in the sun. If you're still attached to the idea that there's some objective Platonic desirability in every attribute we compete to display, good luck reconciling these kind of contradictions.
Our life is frittered away by detail. Simplify, simplify! A man is rich in proportion to the number of things which he can afford to let alone. Thoreau
Money is always useful, but it's increasingly not the main bottleneck.
By contrast, only the elite can get away with dressing like homeless people. Mark Zuckerberg's trademark hoodie is a countersignal that he's powerful enough to ignore even the most high-class social conventions, and doesn't have to worry about being confused with your typical scruffy kid. Bill Gates rocks a $70 Casio watch. Warren Buffett still lives in the same modest house he bought in the 1950s. These are the richest men in the world, and everyone knows it. Not competing on this axis only increases their prestige: they've got enough going on that they don't need to engage in such transparent attempts to gain status.
Look at your iPhone, which combines the function of hundreds of different tools within one sleek rectangle of glass. Think about how websites have changed from the 2000s. Compare Google's homepage to Yahoo's. Negative space is high-status. Clean design is high-status. Clutter is low-status.
It takes a huge amount of skill and effort to make anything complex appear 'simple', along with tasteful discernment, and a dash of courage: instead of hedging your bets, you have to stake your fortune on what you believe is worth elevating, and sacrifice everything else.
Talk is cheap. What matters is taking action that actually requires you to sacrifice something: preferably money, but also time, or reputation.
The author of the Gospel of Matthew was perfectly aware of this inequity, but it took almost 2000 years to make it into the scientific lexicon. The Matthew effect is still widely underappreciated today, not only for its strength, but its sheer pervasiveness: financial inequality, academic citations, scientific discoveries, early childhood education, investing, poverty, fame, popularity, physical fitness, market pricing, and beauty are all governed by the principle of cumulative (dis)advantage.
My guess is that the parable of the talents is meant to describe the harsh reality of the world, rather than suggest we should be OK with it. After all, Christ certainly wasn't.
If you want to have an impact on the world, it helps to make yourself strong first.
The expanding frontier of human knowledge is cutting through the fog, but the clouds of uncertainty gather faster: the world is only ever becoming more dynamic and unpredictable.
Forecasting the interplay between the markets, governments, and technologies of 8 billion people is a fool's game.
As our world gets weirder, the problem of decision-making under uncertainty gets harder, which makes it more important to maintain optionality.
Big wins are always mediated by some element of randomness, which means there is no guarantee of a spectacular success.
The best strategy for getting lucky is collecting open-ended options with potential for massive upside. We can never be sure if these will pay off, but by systematically putting irons in the fire, we maximise our chances of hitting the big one.
The one exception is Nassim Nicholas Taleb. No other asshole, alive or dead, has influenced my life and thinking more. It's not even close. Thank you for your work, Nassim.