sometimes when my players beat a challenge i feel mopey and defeated. i tell them i want to give them a pleasing challenge, but when they win, it is a small unpleasantness. i want there to be more conflict, i want them to suffer. i want them to take large amounts of damage, to struggle, to be wounded. i want them to die.
on the other hand, when they suffer a great setback, it is a blow to me. i created a disease that halves their hitpoints and can be communicated easily. they stumbled into it and were stricken, i thought they could remove it handily but they had no way to cure disease, and i became very worried for them, and sort of upset. what if they died?
in my whole mind, i do want the game to exist in a zone of appropriate challenge. a challenge that is stimulating and engaging, inviting, malleable. difficult when it needs to be, easy at other times, but neither too easy nor too difficult. goldilocks challenge at all times. expanding to meet their expanding tactical knowledge, contracting a little when they are tired and cranky. allowing opportunities to choose areas of greater challenge, and sometimes forcing greater challenge upon them.
there is an area of the dungeon that damages them every time they move, and the monsters they kill resurrect with new powers. once they went too deep too quickly and were faced with shadows with could sap ability points. they decided to avoid it entirely. there is another area that was entirely filled with acid slime, this they decided was a pleasant challenge, and they tackled it and beat it instead of progressing the obvious route.
but it stings when they win, and i am cheered when i create an encounter that poses a threat. they are very powerful now, they are level 17, and they have many magic items that they exploit to great effect, whose effects i didn't bother to think through when i made them. sometimes this is because i like to give us a challenge and see what happens, and sometimes this is because i wasn't thinking ahead. right now my personal foe is their ability to teleport out of combat when the tide turns against them--this gives them a panic button, and my ability to really press them into a tight spot is very limited. on the other hand, this gives me the liberty to create encounters that greatly outmatch them, or that require specific tactics or spells that they may not have prepared at any given moment.
i find that i consistently underpower the monsters in terms of damage. when my players are badly damaged and close to death the game can become stressful. but it is necessary to provide a real challenge in order to create a game that is more engaging. this balance has led us, over the years, towards greater precision in communication. we take things a lot more slowly when the game gets dangerous, so we all know we have earned it if and when someone dies. it would be horrible if one of the characters did actually die and couldn't come back, through soul annihilation or disintegration or something. it's a hard tear in the game.
ragnar the level four ranger almost died in my home game last week. i gave them the choice the week before between using a death and dismemberment table ("hardcore") or normal 5e rules ("normal"). we went over the rules carefully and they chose normal. this is good, it lets the monsters do large amounts of damage without worrying too much about permanently dismembering the characters. and when ragnar was attacked by a greasy leather torture guy wielding an iron maiden, and was trapped in the iron maiden at 0 hitpoints and taking damage at the start of each round, i felt comfortable letting the rules tick him blow by blow towards death. they managed to pry open the iron maiden at literally the very last moment before his death, and it was a huge moment.
i wonder if i'm holding myself back a little from creating scenarios that could result in a TPK. what are the sorts of scenarios that might earn an TPK? what would we do if that happened? it's hard to even think about. but it has to be at least an imagined possibility. my home game is still fragile, but my high level game has so many escape routes and they're so tough, it would have to take place somewhere hard to escape from, in a high stakes situation, and ideally, one they have somehow earned, or at least chosen to participate in. we'll see.