Be warned, this is basically just a gushing review for one of my favourite books, Lying for Money (2019) with a little bit of essay sprinkled in. I'm not sorry.
I'm now at my job for long enough that it no longer feels like a new job, and it has become simply "job". Mainly for that reason, it sometimes no longer feels like something I've voluntarily chosen to do, aligning with my personal goals, etc. Instead, I'm starting to feel like I'm spending most of my day working for someone else's benefit1. I often would rather just hang out with the cat at home, actually - confirmed by me taking a random day off and hanging out with the cat at home while assembling furniture.
So it follows that I have gained a newfound desire to be rich.
I'll start by daydreaming about quitting my job, which goes into making half-baked entrepreneurship plans. Most of them run into the same issue that I also can't hang out with the cat all day if I'm hustling around with a startup or whatever.
So, I start to scheme. I dream up wildly original get-rich-quick fantasies - I do not have the moral character to immediately discount cheating on principle. I'm weak and lazy and kind of greedy.
The thing that always stops me is that the payoff matrix is terrible. This isn't cope! Fraud without the typical downsides of getting caught is just legitimately high effort. The more I researched specific frauds, the more it seemed like work. So much work, with so much risk, which means stress, for gains that tend to disappear as soon as the jig is up.
The labour of fraud is inherently one that pays off poorly in the iterated game of life. Honest work tends to create relatively durable products, but the products of fraud are always on borrowed time. I have a genuine preference to live my life in ways that do not involve constantly scanning the news to see if I need to flee the country today, since that would really put a damper in my ability to hang out with my cat in my apartment.
Love of the Game
The problem is I don't like lying. Sure, I can lie when I need to, but I always feel a twinge of discomfort. While not universal, this is probably very common, to the point where Sasha Chapin, a blogger I look up to, claims that lying causes writer's block. That is generally true for me.
On a pure mechanistic level, fraud is just a lot of work. One must manage multiple realities and occasionally create artifacts of some realities existing if the natural reality isn't cooperating. A successful fraudster is distinct from the merely deluded2 in that there's enough intent to deceive, which implies an ability to notice the gap between what they're trying to sell and what they (and other people) perceive.
There's a bit in Dan Davies' Lying For Money, about the fake colony of Poyais, where he described the lengths that Sir Gregor MacGregor went to con investors and would-be colonists, including writing a whole-ass book3. "Even a master fantasist like Sir Gregor spent a lot of his time calculating agricultural yield tables and dealing with land claim documentation," writes Dan.
Behind every scam is a surprising amount of work, which is wild, because isn't the point of doing a scam to be lazy and not work?!
Then there's the stress. Also from Lying For Money, rogue trader Nick Leeson apparently destroyed his teeth by stress-eating tubes of fruit pastilles (and later nearly died of stomach cancer in prison).
The only fraudster who really got away with it, and probably didn't even suffer that much, was a guy called Leslie Payne, who got to die peacefully and doesn't even have enough criminal notoriety to get his own Wikipedia page. He wrote a book after, which was effectively just nitty-gritty details on all the frauds he did.
Payne actually exited without getting murdered4 because he was so deeply involved in all the operational details. He spent a ton of time writing letters and referrals and managing his various scams, including setting up an overseas bank in order to setup an insurance company at one point. And then one day, when the going got murderous, he exited, and never did this sort of thing again.
This is really, really rare for fraudsters. Usually these people have One Weird Trick and they keep trying it until they die 5. Other than weirdos like Leslie Payne, who realised that even if you specialise in scams, you still have to do a bunch of basically invisible work, fraudsters generally have a core belief in such things as "free lunches", "easy money", "money for nothing", and a lot of them kind of don't have much of an overarching plan - they commit fraud in service of something else, and that never works out well for them.
In other words, there's no getting around it - fraud is still a ton of work. Like everything else in life, if one aims to get rich, or famous, or to get to breed a lot of pigeons6 by fraudulent means, instead of engaging in fraud for the love of the game, the slip ups are inevitable. And the stakes are ridiculous, compared to a non-fraudulent life.
It's Rotten Work But It Also Gets You Jailed, Murdered, or Generally Despised
Either you live in a low trust society, in which case you need to put in enormous amounts of work to get into a position of trust such that you can actually execute a fraud, or you're in a high trust society, which gets to be, and stays, high trust by having very effective enforcement mechanisms.
You don't have to take my word for this, by the way. Just put some serious effort into brainstorming a fraud where you can obtain, let's say, $1M in 6 months, and you avoid prison, getting murdered, or having to flee the country[^11].
If you truly come up with something that will actually work, consider whether this is significantly more work than just turning up to the average 9-5, and whether the risk is genuinely as low as you think it is. And get someone else to check that it's actually watertight, because compared to regular jobs, the stakes of fraud are crazy high.
Does the name Melissa Caddick ring a bell? She's a Sydney woman who ran a pyramid scheme misappropriating other people's retirement nest eggs. She abruptly vanished late-2020; three months later her severed foot washed up on the beach.
The absolute best case scenario for her is that she cut her own foot off to fake her own death. The police's main theory is that she killed herself as she couldn't figure out an exit. A small but not zero possibility is that an irate investor / victim killed her and then dumped her body off the cliff. We'll never know - by the time they found her foot, it was too decomposed to do anything other than some basic DNA testing to confirm that yep, it's definitely hers.
Let's talk about Nick Leeson again. He'd wrecked his own health and marriage. You'd think that while he was making trades with misappropriated company funds, he was living the high life, but compared to someone in a similar position legitimately.... not really?
In fact, he'd managed to 'steal' about $1.4B USD while getting approximately none of the personal benefits of a billion dollars, other than being seen as an exceptionally high performer by the London office (unlikely to be worth $1.4B of 1995 money). Effectively, he destroyed a bank and went to prison to... avoid a bad performance review??? Bro, this has to be the worst trade in the history of bad trades, so of course this trader made a trade so awful that his employer became insolvent.
The famous fraudster of our age, Elizabeth Holmes, set up an entire fake lab for Joe Biden to visit at one point - and still went to jail. Think of the opportunity cost - if she'd just let it implode back in like, 2008 or something, like all the other insane moonshot startups of the time, rather than try such drastic measures to keep Theranos going, she'd have had another decade-plus to found more insane moonshot startups. In another timeline, she could be out here breathlessly presenting about how her revolutionary AI thing is better than everyone else's instead of serving an 11 year prison term.
Why do this? No one sane would do it if they could predict how bad things would go in a relatively short timeframe. Presumably none of these people had a five-year plan that involved being dead, best case scenario missing a foot, or in prison; and they were all executing on schemes sophisticated enough that they had to be the types who have enough brains to do decent risk/benefit calculations for everything else.
The expected value calculations are so awful that no one in their right mind would do this under normal circumstances - after all, the schemes are so harebrained that people need to be tricked into giving them money. Fraud is a crime of deceit, deluding the victims into doing something against their own best interests. With only a few exceptions, fraud has such a shitty ratio of risk-reward that the first person the fraudster needs to delude is themselves.
Which is where we get to the weird frauds, which Dan Davies found so interesting that he wrote an entire other book about just these types of 'non-fraud frauds'. Instead of being a crime of deliberate deceit, in these enterprises, it's usually unclear if everyone involved is constantly lying on purpose, or if they genuinely buy their own bullshit.
Given that fraud with provable intent is swiftly and heavily prosecuted, but all accounting, judicial, and even social systems struggle to inflict Consequences on someone who is "merely" delusional about their managerial prowess, the incentives point to, well....
It is difficult to get a man to understand something, when his salary depends upon his not understanding it.
Still, incentives aren't everything. By rights we should all have abandoned our higher faculties in service for greater paycheques - in practice it's only a rare breed who have such superpowers of credulity.
For most of us, we notice. We can't fail to notice it - the gap where there should be work of substance, done competently - but everyone who's nominally filling the gap is either unequipped or uninterested doing it well. Most people at least notice it when they're personally inconvenienced, but many of us are also bothered when we notice it on the supply-side.
This is when the imposter syndrome kicks in. Contrary to popular belief, I think imposter syndrome is an incredibly valuable signal. Imposter syndrome is a way your brain tries to communicate that things are not alright.
A Natural Defence From Delusion
The typical advice for dealing with imposter syndrome is 'fake it till you make it'. I think this is insanely irresponsible and ultimately harmful.
I've concluded that this so-called "imposter syndrome" is a self-preservation signal, and I say this with the benefit of hindsight. Things just did not make sense.
I followed a lot of stress-reduction advice, like "take personal time to recuperate" - which was how I came to the conclusion that I'm not the problem. An actually insane person, with distorted thought patterns, is likely to bring those distorted thoughts everywhere. My distortions only seemed to happen at work. I finally figured out there was nothing wrong with my eyeballs - my work was just a maze of funhouse mirrors.
It makes sense to hate this sensation - it's profoundly uncomfortable. That's how we figure out what's real. It's a danger signal - if your assumptions are wrong, then you don't actually know what's ahead. Doubt in your gut saves you from the herd of furious hippos that you didn't know about. Obey the doubt, and you can avoid the hippos.
But consider a new scenario: you're not alone, walking towards the hippo swamp, free to follow your gut feelings when they say "hmm, this isn't right". Instead, you're with the chief in the tribe and two of his best friends. All of you have spears, but the chief has the best, sturdiest spear, and his two buddies are the most jacked up cavemen in your tribe. Your spear is like a fucking toothpick against these two. You're like a fucking toothpick to them.
Our good friend the chief of the tribe is loudly and confidently declaring that the plentiful meadows teeming with delicious antelope and beautiful women are right down this way, you all just need to keep on moving, except you're pretty sure he's wrong. You've never seen these plentiful meadows around these parts - in fact, you distinctly recall someone warning you about a hippo swamp somewhere in these parts.
Now does it feel like a good idea to voice your opinions, and hold firm to the truth? Or does it feel safer to go along with the delusion?
Perhaps you remembered wrongly. Perhaps the chief is actually right and there will be a lush meadow if you keep following him! The chief and his huge two goons are right here, while the angry herd of hippos are still hypothetical at this point. The safest thing to do is to agree - and if the chief and his boys seem to be twitchy, you'll probably want to do this enthusiastically. The parts of your brain that does social interaction will help with gusto - it's literally life-and-death here. It has noticed that you disagree with some Powerful People, so it is urging you to bring yourself to agreement, stat.
But the parts of your brain that deal with actually understanding the world will protest, quietly, even if you loudly praise the chief for his insight and wisdom and keep following him towards the hippo swamp. The parts of your brain that independently observes information and comes to a conclusion will keep whispering that "this isn't right. He's wrong. Don't forget he's wrong."
It won't let you forget, because as soon as the chief and his goons come face to face with the hippos, you need to run the fuck away. So it tells the body to pump you full of stress hormones. As soon as the four of you set foot into the swamp, when the biggest hippo rears up to maul the ever-living shit out of your idiot chief, your body will be ready to scamper up the closest tree, ideally before an angry artiodactyl bites your nuts off[^12].
That's my theory of what's happening on the hardware level, but obviously most of us don't live in that world anymore. Even though it sometimes feels like it, a corporate meeting room is not a situation where disagreement will result in you being bludgeoned to death immediately.
Still, this feeling is useful. Anxiety generally promotes restraint, and restraint from people who don't know what they're doing is good. Imposter syndrome stems from the same place as your self-preservation instinct, which will similarly restrain you from taking any drastic action based on anything you say when somewhere deep down, you know you're talking out of your ass..
Instead of setting up the fake testing workflows like Theranos, you simply fail to produce results. Investors, clients and customers alike conclude (correctly) that you're just incompetent. They'll probably stop giving you money, but you won't go to jail - you'll be free to start another ineffectual startup that predictably fails to deliver anything.
It's a genuinely useful feeling that is demonised for its effect of dragging down 'productivity' - but it's genuinely good to take your sweet time meandering into the hippo swamp as long as your idiot boss isn't actively jabbing you with a pointy stick.
Okay, maybe this is just me, though, someone might retort. My imposter syndrome is real and crippling, but I do utterly believe in my company's mission statement, and all my coworkers are respected professionals -
Alright, then. A quick check - does this so-called imposter syndrome only occur in a specific setting? Or in the presence of specific people? Does the imposter syndrome affect your workouts, or are you able to accurately assess your ability to run or lift weights? What about hobbies? Are you in doubt about your ability to play a musical instrument alone in a room?
Prod the feeling until the truth comes out. Journaling will help with that.
This is terrifying because it might require some hard work at the end of it. I discovered that I wasn't a real engineer in many important ways - and I'm feeling much better these days because I'm taking real measures9 to close the gap between what I think I do, what I want to do, and what I actually do.
But what's the alternative? Just sit there and get paid for validating someone else's delusions? Sit with the feeling that what you're saying does not match what you're seeing and feeling? Follow your boss into the hippo swamp?
The World Is Rotten Work
My new job is tedious as hell at times. Today I spent most of my daylight hours selecting and naming photos and entering them into a spreadsheet, which is, unfortunately, not hanging out with my cat in my apartment.
Am I lowkey furious about that? Oh yes, I absolutely am. Some days I'm so pissed off I can barely breathe. Other days, I manage to reach some sort of equanimity about it. It's not an unfamiliar rage, to be honest - I've thrown dozens of similar tantrums when I realise I hadn't done my laundry, or the ingredients I've procrastinated cooking for the week have gone moldy, etc, etc.
Everything is rotten work. It's all a tedious grind, no matter what. It would take a miracle to convince me to actually do work, day after day.
Luckily, I've come back to this draft on a different day, when I remember the miracle. The miracle is the world - the self-evident world full of people and institutions and things that have been designed, built, created. The human-made world, every part of it, is made of this miracle - this basic persistence of honest work. People who look around, see what actually needs to be done, sigh, and get to work. Day after day, week after week.
The miracle of my education involved dozens of people who woke up every single day, drove in on a tollway which ate their already meagre wages, coming to my primary school to teach me how to read and write and count and multiply - every single day for years on end. My education was rather on the totalitarian end, especially when I was very young - but I am absolutely grateful to have been surrounded by literal scores of adults forcing kid me to drill multiplication tables and writing (in two very different languages!). I simply would not be this competent and natural with maths without the very, very concerted efforts of many many educators, and I would not be able to use my mathematical abilities now to tell people how to keep massive concrete structures standing for years and years.
My work is bulwark against entropy. All honest work is like this - you create something out of nothing. You create a path for the vital to get to where its needed - lifesaving medical care where there otherwise isn't. Light where there otherwise isn't. Food where there otherwise isn't.
We all do this because it's good. It's good when children grow up to be literate and numerate. It's good when people can get affordable food. It's good to have electricity and the ability to go places.
Some days I can keep these facts close at to my heart, and tell myself that this is the way I bring about the miracle of a Society That Basically Works, A Lot of the Time, For a Lot of People (but with more work surely we can reach and serve Everyone).
I get embarrassingly emotional about strange things. The other day I saw a government public service announcement about how flu vaccines for children now come in nasal spray form, and are free for children aged two to eleven, and I nearly cried.
Does this turn me into some sort of people-pleasing workaholic? Not at all. I still can't give less of a shit about getting to the office exactly on time, as long as it's just a day of desk work - but this feeling keeps me actually working for the full day instead of wandering off to read a web novel at some point.
I can tap into this feeling to push through the icks and the ughs of doing something tedious, all day long, every day, as long as I'm really convinced of its value. My conviction comes from the fact that I know how it feels to lack it.
The world embodies work - all the quiet, unsung work that created everything we have. The fact that I'm alive now, of all times - beneficiary of other people's consistent work - the fact that I'm in a position to work in this machine, to try to make it work better, fairer - I try to consider it a privilege, not a burden.
I love you all, the way the power lines love - anonymously, impersonally, reliably.
He reckons that power lines are a reminder of man's ability to generate electricity. He's always saying great things like that. - The Castle (1997)
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I'm not willing to land firmly on either side at this point and I'm unwilling to hear from either the communist or the grindset crowd at this time, and probably most future times too. ↩
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Although many fraudsters are also delusional and many deluded fools do something that sort of looks like fraud, albeit extremely ineffectively. More on that later. ↩
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To be fair, largely some plagiarised West Indies almanacs... but remember this was the 19th Century and they haven't invented Ctrl+C yet. ↩
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Payne pivoted to basically legitimate business after his gangster associates tried to have him killed. ↩
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Getting arrested is surprisingly not a deterrent! A lot of fraudsters will get out of prison and then immediately try a variant of the exact same fraud. I guess when you've got a hammer...? ↩
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I'm not going to spoil this one but trust me, it's good. Go read Lying For Money!! ↩
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Payne got away with it because he was in league with gangsters who gave him a ready supply of useful idiots to throw under the bus and when he ended that association he just... stopped doing any more fraud. I am fascinated by this crook. ↩
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Or your legs, or head, or... in the course of writing this I discovered that hippos can fit like, half a human adult down their throats and biting a human in half is very possible based on bite force calculations. You can read this fairly gory account from [this guy who survived a hippo attack]((https://edition.cnn.com/travel/article/hippo-attack-avoid-survive-paul-templer). ↩
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Iris does not know I am writing this. I have gotten a lot of value out of her statistics offering; having a rigorous mathematical basis for decisions makes me feel and act way more like a Real Engineer. Also, she's just launched a new offering with an early subscriber discount. ↩