The Top 100 Things I'd Do
If I Ever Became An Evil Overlord

Right!

So, I'm flatly not interested in any kind of Good or Law that you couldn't talk a self-interested dragon into having. But! This is much more than zero Law.

The benefit of trustworthiness is that you are perceived as trustworthy, and the benefit of being perceived as trustworthy is that you reap the benefits of trust. And the benefits of trust are huge; people who are able to trust each other, if they're right to trust each other, will always win against people who can't. 

You can always do better for yourself by exploiting someone who gormlessly trusts you than you can by guilelessly extending the same trust, but that's wholly extractive - it makes one person richer and one person poorer. If you're a highwayman passing through, that deal probably seems pretty good, but while highwaymen are the richest kind of forager, foragers are not the richest kind of human, and if you reap without sowing, the harvest gets thinner each year. Two people together can do more than two free agents; even robbers would rather be part of a band that robs everyone else.

This is more than half of why people gladly suffer sovereigns, by the way; the threat of punishment for treachery is delicious if it'll also be applied to your allies, delicious enough to accept the indignity and humiliation of servility, hence why bandits and pirates and adventuring parties appoint captains and sub-captains instead of just walking in the same direction and figuring things out from there.

The incentive to extend trust - if only it can be made to work - is so powerful that everyone's thinking about it all of the time - very nearly as often as they're thinking of ways to trick and swindle each other, really - and so it's no surprise that even some of the stupidest people alive have found ways to make it work.

But every step in this chain is an important one: if you aren't getting the benefits of trustworthiness, there's no call to pay the costs, or if you can get the benefits without actually having the quality, again, there's no call to pay the costs.

And it is observed that men generally judge more by the eye than by the hand, because it belongs to everybody to see you, but to few to come in touch with you; everyone sees what you appear to be, few really know what you are, and those few dare not oppose themselves to the opinion of the many. [1]

And men are so simple, and so subject to present necessities, that he who seeks to deceive will always find someone who will allow himself to be deceived. Alexander the Sixth did nothing else but deceive men, nor ever thought of doing otherwise, and he always found victims; for there was never a man who had greater power in asserting, or who with greater oaths would affirm a thing, yet would observe it less; nevertheless his deceits always succeeded according to his wishes, because he well understood this side of mankind. [2]

1. The Prince, pg. 44

2. The Prince, pg. 43

Who's Alexander the Sixth? 

Sixth Alex. 

That doesn't actually help.

So you want to be someone that people can trust, but most people are going to trust you pretty much no matter what you do and you don't actually have to be all that trustworthy to 80/20 it. Which seems like an open and shut case against Law, or at least one Aberian Arvanxi feels that way. 

You disagree?

Well, even if I agreed completely I think he'd still be making a mistake, since detecting as Lawful is useful for seeming trustworthy and yet there's more to Law than just trustworthiness, so if you were Lawful enough in other ways even without being trustworthy it'd make you a better conman, so maybe he should give that a try!

But, yes, I also disagree!

Kind of.

Disagreeing with Aberian Arvanxi is fraught, and I don't think he's making huge or obvious mistakes, but I disagree at least a little bit.

If Law prevented you from harvesting fools, when there are so many fools, having Law would be stupid and contemptible, but, while ideally you'd be believed by all men whether you give true promises or false ones, these desiderata are in tension, because not everyone is a fool. A Chaotic wouldn't see any reason to consider "I swear" more binding than "I say," and would say that in a world where some people will believe you if you swear, that you'd be stupid not to use the strongest possible language. But if there's no tell when you lie, the smartest people won't trust you even if you're honest, and if there's too obvious of a tell, even the dumbest won't fall for it. 

People have an endless array of ways to enable trust and catalyze cooperation, but major ones include limiting their exposure in proportion to their distrust, building and minding reputation, avoiding strangers and travelers - or cheating them, it's mostly fine if you have a reputation for cheating travelers because travelers mostly don't know and locals mostly don't care - , relying on family and friends - and other confederates - who genuinely like you and/or have common interests with you that'd make it shortsighted to sell you out for a small temporary benefit, retaining wherever possible the ability to destroy the mutual fruits of your collective labor, feeling in your heart such things as camaraderie and gratitude and pride as can be verified with Norgorber's truthtelling (I roll Bluff and you roll Sense Motive; that's Norgorber's truthtelling), having values and priorities that are sincerely held and make you predictable in certain ways (as can also be verified by Norgorber's truthtelling). Thus everyone must pick where on the spectrum from pure Chaos to pure Law they should sit to capture the most benefit.

Where I come down on that is very principled, I think. If I give my word, I either mean it or I don't. (Or I mean it, but I'm kind of half-hearted about the whole thing and will probably give up on it if something else comes up.) If I do mean it, though, that's already a mark of respect, because either I like you enough or benefit from your existence enough that I'm looking out for your welfare, or else I expect that you'd be able to tell if I didn't. And if I give my word and mean it, then I won't break it unless under extreme duress or suddenly aware of some huge positive advantage. (Unless I was half-hearted from the start, but if someone couldn't tell that from my tone of voice and I didn't care enough to make it clearer, I don't think it's incumbent on me to be nice.) And I'll feel kind of bad about it, in a proportionate way - if the duress is extreme enough that I expect the person I made a promise to would be like "yeah, I wouldn't have expected you to stick to our agreement," then I'll probably feel bad but not about breaking the agreement, whereas if I broke things off because of something minor I'd feel like a weak failure. 

And your dad's doing something different?

I don't think he's making any obvious mistakes. If someone's cooperation really is conditional on his, if their Sense Motive beats his Bluff and they're too smart for him to route around it, he won't promise anything he won't try to deliver.

He's doing largely the same thing as I am, except he'll do it with somewhat less provocation and won't feel bad about it, which, goes my theory, makes intelligent people go a little further to limit how much they're relying on his reliability than they otherwise would.

...Which I don't get the sense that he's upset about, really. He likes it when people trust him, but he doesn't like people who trust him, and it makes him angry when people he does like do. Ask me how I know.

How do you know?

He told me, repeatedly, and since it wasn't to his advantage to admit I know it must be true. He was always really smug when he realized I'd been counting on him to do something he no longer wanted to; he'd see it as a chance to impart one of his famous life lessons. 

My disagreement with him is deeper than practicalities. 

I think that what Inigo and the man in black did was cool, I'm glad that it worked in-universe, and I wish real life were more like that than it is. My father would find it distasteful, be annoyed that it worked in-universe, and, after the play was over - if he could even be convinced to wait that long - the entire way home he'd grumpily pontificate about how the real world works no such way. 

My father would would be annoyed because to him it'd look like man in black did something stupid and was rewarded for it, which is bad writing, but to me it looks like the man in black did something daring and was rewarded for it, which is good writing. Not all daring things are good ideas, but a daring thing that works is inherently cool. 

I'm not saying that the old man errs, or that I do, but if he's making a mistake, I expect the mistake he's making is in believing that the world is less beautiful than it is, because he can't imagine that, and that if I'm making a mistake, it's in thinking that the world is more beautiful than it is, because I want it to be.  

I just plain want to live in a world where beautiful things can happen, like enemies borrowing each others' swords just to look at them, or evil overlords leaving blankets for their prisoners, and I want to be one of those people, and - maybe it's too storybook. Maybe real life can't be that way.

But I'd like for it to be.  

You know, you can decide unilaterally that the world is more beautiful than it'd otherwise be. 

And it's one of my favorite decisions to unilaterally make, but I'm limited by my spell allotment and save DCs in the number of people I can force to play along. 

If I threw you in prison, I'd probably like to leave you a blanket and a mirror, unless I was deliberately maximizing your misery or specifically leaving you without a blanket and mirror as a callback to this list. If life were like The Princess Bride, an Evil Overlord could just say, "I thought about leaving you in a cold cell without amenities, but decided against it. Stay put and don't use the blankets to escape, I'll probably kill you in the morning." And that'd just work. In the world we actually live in, it usually wouldn't work, and from the Evil Overlord's point of view it'd be risky for little benefit, but it could work, sometimes, and it's just plain stylish for someone to successfully pull off something difficult and risky for some marginal benefit. It's an incredible display of competence and self-assurance.

Not all stylish things are good ideas, and in fact this particular stylish thing would not be a good idea, but it's squeezing my soul out through my tear ducts to listen to people like my father and Peter Anspach who don't get the appeal and view people who attempt the difficult thing with contempt. 

The Evil Overlord list is full of great advice, but much of it boils down to "remember to never do anything cool" and I can't help resenting the reminder. 

You mentioned earlier in the thread that Paizo hates to see me win and that's why I was given so many terrible ideas, but my writers did more than nothing for me. Word of God has it that out of all the Adventure Path villains printed by 2016, I'm the one who has the most fun with it.

It'd make me quite sad, to have less fun. 

But of course, "be stylish, have fun, win anyway" isn't a real option on the menu. 

It's just sad to exist in this world instead of one where I have more leeway to do things because I want to. 

And - I still plan on winning, but I admit that this conversation has shaken my confidence, and so I'm least conflicted to implement those rules that'd make me much more effective without ruining any of my fun, and most conflicted about things that make me a little more effective at the cost of making life in the meantime more bleak and sad. 

I normally wouldn't promise this to a supervillain, but if you leave me blankets or a mirror I won't use them as part of an escape plan. 

Why wouldn't you normally promise that to a supervillain?

Because to date you've only ever imprisoned me in comfortable conditions and I don't see it as impossible that you'd continue in that way even after hearing the rule - a hundred rules are a lot to keep track of, and you could forget. Having a blanket isn't important enough to me that I'd prematurely limit my escape options just to guarantee access. 

Then why promise it?

Because you seem sad. 

Less sad than I was.

If I ever take you prisoner, I'll give you blankets and a mirror and a piece of chocolate on your pillow and a little courtesy bar of soap. 

I can't promise not to use the soap or chocolate as part of a cunning escape plan.