Be Slightly Evil: A Playbook for Sociopaths (Ribbonfarm Roughs 1)

by Venkatesh Rao

  The insurance-dominated script building can sometimes show up in a disguised form as experience maximization: you become afraid, not of bad things happening, but missing out on good things. But as the idea of the bucket list demonstrates, fear of “missing out” is simply another manifestation of insurance-driven thinking. If you had all the time in the world, missing out wouldn’t be a worry.

  So why isn’t the insurance bought with dollarn+1 worth less than the insurance bought with dollarn? Because in an open world, you cannot actually estimate probabilities of various scenarios and rationally arrange to buy insurance in the order of decreasing likelihood of various scenarios. Because there are unknown unknowns that aren’t even on your list, let alone modeled and rank-ordered by likelihood estimates. Heck, even for known risks, you can only raise or lower risks in relative ways, not absolute ways. If you avoid flying, you can still get killed in a plane crash if the plane crashes into your house. Underground bunker? Maybe the crashed plane will release a deadly toxin that seeps in.

  There’s a fable in Indian mythology that gets at this. A rich and powerful king wants to be immortal, and gets the gods to grant him a boon. But they don’t offer him immortality, just an insurance policy with explicit clauses. So he asks for and is granted, the following policy: he cannot be killed by day or night, by human or beast, neither indoors nor outdoors, and so forth. Clever, huh? And of course, he gets killed by a half-man-half-lion at dusk, on a doorstep. Talk about black swans.

  This process never ends. You can keep imagining things that could go wrong and destroy the quality of life you’ve achieved (or limit the things you could “miss out” on), and keep spending to secure it better against an infinite universe of uncertainty. That’s why rich people (in my experience) are usually more careful with their money than poor people. Sure, they may splurge on luxuries (that’s their idea of rewarding themselves with a specific lifestyle), but that spending is just the spending on the lifestyle. They save the bulk of their wealth for increasingly complex forms of insurance to preserve those achieved lifestyles. The richer you get, the more lifestyle design becomes lifestyle insurance.

  Hedge funds, cabins in the Wyoming mountains, offshore bank accounts, a private jet on standby to fly you to a safe haven on a secret private island in case the world ends and zombies run amok, cryogenic self-freezing, and the ultimate holy grail of insurance: immortality-seeking. That isn’t just Mr. Burns of The Simpsons. That’s more real rich people than you might think, starting with John D. Rockefeller (who strove mightily to live past a hundred, but failed at 98) to Ray Kurzweil today, who reportedly takes 150 health supplements a day in the hope of living long enough to see the Singularity arrive, so he can upload his brain into cyberspace where it can survive for eternity and beat entropy (he still has to hope multiple simultaneous earthquakes don’t take out all the datacenters where iKurzweil is stored).

  If you ever wondered why your rich friend blows money on a $1000 bottle of wine at dinner, but goes all Scrooge on you if you ask for $1000 to help you build your app, it’s not entirely resentment at being considered a soft touch, or fear of being taken advantage of. It’s also because the $1000 bottle of wine is merely an element of the designed lifestyle he/she is trying to preserve against scenarios via insurance. What’s better than a $1000 bottle of wine? Why, the ability to keep drinking that $1000 bottle of wine even in the event of a zombie apocalypse or the Skynet Hunter-Killers chasing you. That $1000 isn’t in the diminishing marginal utility zone. It actually represents millions in expected costs,against a space of scenarios being insured against. Buying a lifetime supply of your favorite wine is merely the first step. Then you have to put some cases in your bunker on your private island in Greece. Then you have to buy anti-aircraft guns for your island. And a nuclear reactor. And a fall-out shelter in case the nuclear reactor suffers a meltdown. And install a private computer network that Skynet cannot get into.

  I fully sympathize, by the way. We all think the same way, just not on such a grand scale.

  To put this on our 2x2 matrix, when you have no “reasonable” story (reasonable in the sense of “everybody else is following that script” whether or not it is actually sensible), your anxieties are limited only by your imagination. The paycheck-scripted, by the way, aren’t immune to such anxieties. They just find security and comfort in numbers. Collective scripts are more naturally self-limiting. They don’t spiral out of control to zombie insurance as easily. If everybody around you accepts a pattern of insurance, no matter how irrational, you feel safe accepting it yourself and relaxing.

  But to bring it down to the world of people like Kai, you and me, making ends meet and wondering if we’re doing enough, both the millionaire’s situation and our own reflect age-old anxieties about mortality.

  A simple and stark motif for this is a soldier in the trenches of World War I.

  Imagine being this soldier. You are stuck in a boring, tedious, physically uncomfortable situation – cold, wet, eating terrible food, battling disease around you — all while dealing with ever-present death.

  Ask a simple question about this soldier: can this soldier engage in the most basic human relaxation behavior, taking a nap?

  Surprisingly, the answer is yes. Even under such extreme circumstances, you eventually hit a cognitive and physical limit and cannot devote any more intellectual resources to increasing your chances of winning and surviving. You hit a point where you let go, and take a nap.

  The human condition for everybody, rich or poor, in a wartime trench or doing Internet marketing and hoping to move to Hawaii, like Kai, is the same. Whether the immediate situation is pleasant or unpleasant, the overarching reality is that all your future planning and thinking involves scripts that all end in exactly the same way: with your death.

  So the answer to Kai’s question: am I doing enough? is always no. There is always more you can do, all the way to the best available idea for immortality that happens to be around during your lifetime.

  Whenever you are lucid, awake and thinking, you cannot escape the thought that the inevitability of death frames your current situation. It will frame your behaviors whether you realize it or not. The WWI soldier in the trench is always subconsciously alive to the fact that death is a careless stretch away. Whether he is smoking a cigarette, eating cold soup, or staring at a faded black and white picture of his kid, that thought is never far away.

  And so is the millionaire, drinking his $1000 bottle of wine at a fancy restaurant. Mortality may be a more distant thought, buried under more pleasant layers of distraction, but it is there. And it is the same for the desperate experience-maximizer, doing a frantic “if it’s Tuesday, it must be Brussels” tour of Europe.

  But just because there is always more you can do – and you should, it is the definition of being alive in a way – does not mean you cannot take a nap.

  So take that nap. Mortality will always be staring you in the face when you wake up, and you can always fret about the next bit of insurance you can buy with your next dollar when you wake up in 45 minutes. Some days, mortality will stare you in the face close up. Other days it will be a subtle and quiet note at a fun party where you’re immersed in the pleasures of the moment. But it’ll always be around.

  I hope, Kai, that this was not an entirely useless answer. Relax, take a nap. You can get back to freaking out when you wake up.

  Now I need a nap.

  Pistols, at Dawn

  Here is a case study on handling a work situation, from a Be Slightly Evil perspective.

  K, a middle-aged single mom, who worked hard to put herself through graduate school while working a day job as an admin assistant, found a new job as sales analyst in a Fortune 500 company where big, bear-hunting teams go after multi-million-dollar corporate sales. Within the first couple of hunts, she realized that a particular senior sales guy–call him J–was treating her like a secretary. Innocuous “requests” like, “could you add this note to slide 12” and “could
you clean that up before you print off copies for the client meeting” started coming her way. K did not report to J, but both reported to a sales manager T, who had a laissez-faire style. The entire sales team (which included several others, including an actual admin/editorial assistant) worked in a fluid, “collaborative” way, with group emails flying around (with the usual tactical cc’ing and backchannel sidebars). A typical modern workplace in short. J’s “requests” were never direct commands, but she found herself complying anyway, and getting stuck with tasks she used to do in her old career. And shut out of higher-value tasks that she could do and wanted to do (and had paid big education-dollars to learn to do).

  K emailed me right after a particularly egregious email (part of a long straggling exchange of multiple emails) from J. She wanted to know how to respond to that email to “fix” the whole situation, and be treated with the “respect” she “deserves.”

  Here are my analysis and recommendations, minus some irrelevant situational details:

  There are several good ways to deal with such toxic email exchanges. K had thought of a couple of bad ones, and I could immediately see a half-dozen better ones. Unfortunately, none of them would have been particularly effective. Even worse, I could suggest a one-off response to K, but she clearly lacked the email-fu skills to sustain the elevated level of sparring without continued babysitting. Consciously studying and improving email-fu skills in the heat of battle was not an option either. I would have done K a disservice by just suggesting a one-time tactical email band-aid. It would have merely prolonged her misery.

  The problem here with K is that she forgot the first rule of dueling: as the challenged party, you need to exercise your prerogative to choose the time, place and manner of combat. That is the great advantage in being the reactor rather than the instigator. Don’t choose a drunken fist-fight in a bar simply because that’s where the challenge was thrown down. If pistols at dawn work better for you, choose those.

  In K’s case, the problem wasn’t really created by J, the tactically-superior email-fu warrior. It was created by K failing to recognize the consequences of working, at her interpersonal-skills level, with the lazy, conflict-avoiding manager T, hiding poor team management skills under a facade of laissez-faire management. K’s problem was to deal with default unfavorable perceptions (female in a male-driven workplace, with a known “secretary” history, and ingrained, easily-triggered behaviors, in compliant “administrative assistant” mode). Fighting one J at a time, one email exchange at a time would be impossibly hard. Email is a medium ideally suited to small, real-time perception corrections, achievable with a couple of sentences mixed judiciously into routine communication. It is a terrible medium for making large perception corrections or setting favorable defaults.

  One ideal-case what-if is instructive to consider. K would have had a backchannel chat with T early in the engagement, at the very first sign of “secretary perception” issues, factored in T’s laissez-faire style, and suggested that T clarify roles, responsibilities and expectations at the next planning meeting. A more thoughtful manager than T would have done something like that without being prompted.

  This is still a difficult task, but at least it is merely one “crucial conversation” instead of a hundred email-fu fights between a green belt and a black belt. Handling such “perception setting” crucial conversations is an essay-length topic in itself, but I’ll provide (as I provided to K) a brief hint on how to manage those. The wrong way is to honestly explain the particular situation bothering you (“J is treating me like a secretary”). It puts you in “complaining to Mommy” mode, which all managers, laissez-faire ones in particular, hate. Most managers are terrible in Mommy mode, even if they sincerely want to help. It also risks poking at specific and dangerous interpersonal histories which you may not know about (J-T in this case). One right way, for someone like K with her level of situational information and skill, is to flatter the “management style” conceits of the particular manager and make an abstract suggestion. In this case, something like this might work: “Really like your style, and how you don’t micromanage us; I expect you’re going to do a basic roles/expectations thing at the next planning meeting, and then put us on autopilot?”

  This will not work in all cases, but seemed like an appropriate stab given what I’d been told about T. A different T may be too lazy or scared for even this much managerial work, or need more direction and hints on K’s expectations of such a meeting. Or T may be smart enough to detect, and thin-skinned enough to take offense at, the back-seat driving and the somewhat transparent flattery implied in the “you’ve probably already thought of this” idea attribution. The point is, you can devote enough time to prepare for this conversation, pick the right attack and make it count. And you won’t have to juggle real-time operational details at the same time. If you are truly forced to “solve” a difficult interpersonal meta-problem in a reply to a specific email, while dealing with the actual work-content part of the reply, that’s a tough situation to be in. Don’t put yourself there if you can help it.

  In the ideal case, if the crucial conversation had succeeded, the favorable initial conditions would have created many more opportunities for K to start building up a true “sales analyst” perception, provided her with a more controlled email-fu learning environment (while handicapping people like J, for whom laissez-faire is an advantage), and laid the groundwork for any subsequent intervention needed from T.

  For K, it was obviously too late to do this in the specific situation. It was late enough in the engagement that she’d already been labeled, ‘secretary type’ and through her actions, signalled assent to the label. All the email options (we’ll examine such tactical options sometime) would have had a high cost and/or a poor chance of success. The good news: such situational damage is not irreversible. If, in the next engagement, with the next team, K reads the team members accurately and initiates the “early context-setting” strategy successfully, she will start building a solid and advantageous perception. A temporary email band-aid in response to J was still required of course, but less would be riding on it (I suggested a couple to K, after making sure she understood it WAS a band-aid and not a solution).

  Moral of the story: you can’t always pick your battles, but you can choose when, where, how and with whom to fight. Isolated tactical problems are very rare, and if you are seeing any situation as “how do I respond to this email” or “what do I say in this meeting,” chances are, you are misframing a broader problem and heading towards your personal Vietnam. There are no formulas. Eyes-wide-open analysis of complete situations and contexts, followed by a deliberate choice of when, where and who to “work” to get where you need to be, is the only way. And this analysis must be informed by self-awareness and understanding of your own limits and others’ personalities in the equation. The analysis must be turned into action through a mix of immediate band-aids and well-timed strategic interventions. And after all that, you will still fail often, since there are always uncertainties you cannot model. So you course-correct at multiple levels with feedback.

  The good news is that this comprehensive approach leads to “investment” rather than “spending.” Rather than every interaction starting from square one, you gradually accumulate a favorable perception/reputation and a repertoire of adequately-practiced skills. It’s like gaining new weapons faster than you lose lives in a video game.

  How to Interrupt

  I unconsciously learned how to interrupt effectively, by watching and starting to imitate a senior executive who was really good at it. But I didn’t realize I was doing it, or understand why it worked, until I read Impro by Keith Johnstone. The ineffective method is to wait till the interruptee has finished making the point you disagree with, form a response in your head, and then interrupt with something like, “excuse me, but...” or “sorry for interrupting, but...”

  Here’s the effective method: you need to interrupt as soon as you’ve roughly unde
rstood that there is an objectionable point being made (which can be before the speaker has finished making it), and before you’ve decided what to say. You do so by thinking out aloud, going “Aaaaaahhhhhhhhh!” or “Ehhhhummmmmm!” clearly, and stretching out your interrupt phrase over several seconds, until the interruptee shuts up and looks towards you. And most importantly, it should be patently clear that you haven’t yet decided what to say, and are thinking about it. This means looking up, down, or away in the distance as you normally would when you are absorbed in thought, not directly at the interruptee. Don’t try to stage this. An artificial use of this tactic will be transparent to smart people. You should actually start the interrupt at the real right time (based on the content of what’s being said, rather than the formation of your intention of “I need to stop this”), immediately tune out the room, and start shaping the response in your head. The quality of your timing will tell the other smart people in the room whether you know what you are doing, or faking it.

  Why does this work? As Johnstone explains, it is primarily a status thing. Important people feel confident enough about their situational status to effectively say, “I disagree, but I am important enough that you should all shut up and wait while I figure out why, even if it means wasting 10 seconds of everybody’s time.” In terms of rhetoric, the timing matters, because if you wait till you’ve formed your response before interrupting, it is already too late. The interruptee has likely used that point, introduced other points, and moved on with the construction of his/her argument. It may be too late to arrest the momentum. There are other subtleties here, about why and how this works, but rather than work out all the implications, I’ll do one example and leave you to work out others. The example: you don’t have to look or sound super-confident, but it should be clear from your body language that any uncertainty you display is associated with the real-time thinking you are doing, not the social appropriateness of the interrupt. A great example of doing uncertainty right is Vincent D’Onofrio’s Robert Goren character in Law and Order: Criminal Intent. When he interrupts (usually with this method), he always looks uncertain and fumbling, but still communicates mastery and control of the situation.