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

I'll think about it.

Is that code for "I'm never going to bring this up in the hope that you forget"?

You're the one who said it, not me.

On another topic entirely, apparently we're not allowed to leave until we've gotten through all hundred of these, so... sixty-five?

...No, let's just pull the splinters all out today at once. Ileosa knows that she's breaking rule sixty-four, and just doesn't want to look squarely at how, but she's an adult, she can handle it. 

Remind her exactly how it goes?

64. I will see a competent psychiatrist and get cured of all extremely unusual phobias and bizarre compulsive habits which could prove to be a disadvantage.

Ileosa's "extremely unusual phobias" include but probably aren't limited to: snakes, things which make her think of snakes, things which put her in mind of pit fiends (she'd include "pit fiends," but that wouldn't count as extremely unusual - everyone with sense is afraid of pit fiends), being out-of-doors at night, owning up to failure, and sleeping with men. 

Her bizarre compulsive habits include: wanting to make every strong and beautiful women she falls for obey and/or love her, cutting up faces to mark her territory and make them worth less in the eyes of others and take away the places they could run and the people they could be, plotting and betimes enacting disproportionate revenge on people who disrespect her or outshine her or just get uncomfortably close to outshining her, and compulsive one-upmanship. 

If Ileosa cares more about winning than she does pandering to her neuroses, probably the ones she needs most to be cured of are ophidiophobia, nyctophobia, androerotophobia, the harem-collecting thing, the mutilation thing, the disproportionate revenge thing, and the compulsive one-upmanship thing.

It's just - gods of the Pit, it seems so joyless and miserable. 

I don't think you need to sleep with men if you don't want to.

Why not? Seducing men and boinking them are two of her best skills. She stopped doing it when Eodred died and she gained more hit dice and class features to compensate with, but that doesn't mean that it doesn't have a rightful place somewhere in her toolbox. Ileosa doesn't have any other good way to handle, say... Toff Ornelos. His class features are stronger than hers, she can't really bribe him with the wealth of the state because if she's deposed he stands a good chance of inheriting the entire kingdom, and he's both the more skilled mage than her staff wizard and also has way more wizards in his employ. But would seducing him work? Maybe it would, maybe it wouldn't, but the point is that Ileosa never considered trying. She just thought "oh, yay, Eodred's dead, Venster's dead, that means I'm free, I don't have to have sex with men." 

Not wanting to screw dudes isn't a phobia, let alone an extremely uncommon one!

Most women don't seem to have any trouble with it?

I really don't think you should force yourself to sleep with people you don't want to.

It seems intuitively like I should, since I'm good at it and it's worked for me in the past? Is there a trope-logic reason why I should expect seducing Toff Ornelos to be less likely to work than it looks, or is this just you being Good and not wanting me to suffer through anything no matter how trivial or worth it?

I don't want you to suffer through anything but also I don't - for context, if you could magically get all the benefits of seducing Toff Ornelos without having to do it, but you had to give up, say, the face cutting thing, would you rather do that or get the benefits by seducing him?

It's hard to bring myself to want either, but... I'd rather give up the face cutting?

Definitely a close thing.

I don't want you to suffer through anything but also I don't think this particularly trivial for you, or particularly worth it.

Oh, come off it! 

This whole time you've been saying that "even though it takes some fun out of the job," I should quit everything that I do for fun, if it isn't fun for someone else, because that's what makes me more likely to win in the end. Now I bring up something which would take some fun out of the job, and doesn't really hurt anyone else, and now you're up in arms? 

What gives?

At the end of the day, even if you do everything on the Overlord List, your odds of winning are better but that doesn't make them good. Like I've said, the heroes tend to win in the end. Some of the Overlord List rules, if you follow them, improve your odds of getting a redemption arc in the epilogue, or, if there's a Greater-Scope Villain or Man Behind the Man I haven't met yet, improve your odds of a survivable Heel-Face Turn in the third act - although others very much don't. I'm least conflicted about the things which it wouldn't hurt you to implement and would make you more effective while also harming others less. I'm more conflicted about the things which hurt you to do, but make you more effective while hurting others less, and the things which don't hurt to do and make you more effective without hurting others less. I'm not conflicted about things which hurt you to do and might make you marginally more effective without doing less harm to others, because those are just terrible. How could I feel happy about you doing something you hate when I don't expect it to help you in any lasting way?

Ah.

Thank you for sharing your view, and thank you for trying to look out for me. 

But I'm not planning for failure, here. I'm still trying to win.

Sixty-five?

65. If I must have computer systems with publically available terminals, the maps they display of my complex will have a room clearly marked as the Main Control Room. That room will be the Execution Chamber. The actual main control room will be marked as Sewage Overflow Containment.

It's already the plan to doctor or destroy any public floorplans that there are for Castle Korvosa.

I might set Togomor on hunting down and silencing retired servants from administrations past, although maybe that's an easier excuse for Paizo to give as to why the players can't find this information than it is a strictly optimal optimal use of Togomor's spells and time.

Sixty-six?

Sci-fi trope:

66. My security keypad will actually be a fingerprint scanner. Anyone who watches someone press a sequence of buttons or dusts the pad for fingerprints then subsequently tries to enter by repeating that sequence will trigger the alarm system.

Sixty-seven is cloaked in sci-fi terms but is more broadly applicable than that:

67. No matter how many shorts we have in the system, my guards will be instructed to treat every surveillance camera malfunction as a full-scale emergency.

A full-scale emergency? You'll run out your minute buffs chasing mundane rats.

And if my guards were instructed to treat every delayed check-in or whatnot as an emergency instead of as possibly-an-emergency, a possibility which grows in their minds the more the delay deviates from what they've come to expect, they'd stop doing that and instead start doing the other thing.

Is that why in the sixth and final installment of CotCT an adventuring party is able to take your castle room by room like a dungeon with six floors?

...

If you switch sides, I'll appoint you seneschal of the castle and you can rework our security.