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Many video games are all about leveling up and gaining new powers, talents or weapons as you progress through the game. Sometimes, however, the game will flip the script and make you choose a handicap for yourself instead.
Whether this is more or less frustrating than simply being slapped in the face with a disadvantage can vary: on one hand, you may be able to find the option that impacts your strategy the least, or in some cases even helps it. On the other hand... it's a Sadistic Choice in gameplay form that can make you feel like you're being sat in front of a group of venomous insects and asking which one you'd rather have bite you. One particularly bleak usage of this trope is when you're fighting a losing battle and all the game lets you do is decide how you're going to be gradually weakened before your inevitable defeat.
Sometimes these handicaps are optional. The player is often given Hard Mode Perks for taking these additional challenges. Of course, sometimes players will subject themselves to these just for the additional challenge.

Examples
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Dicey Dungeons: In Episode 6, each time your character goes down a floor, the game randomly selects a new rule from a hidden list, and the player may either take the rule shown, or a second random selection. Some of the rules handicap both the player and the enemy, and some appear balanced but are harsher than they look when you stop to think about their implications; but some are straightforward handicaps for the player or buffs for the enemy. And if you don't like the proposed rule and choose a random selection, you always risk running into one of the really nasty ones....
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StarCraft II: Wings of Liberty: The campaign's penultimate mission essentially asks you whether you'd rather face hordes of Zerg fliers or be harassed by Nydus Worms popping up everywhere in the final mission. You can either do Shatter the Sky and destroy the orbital platforms where the Zerg air force resides, or do Belly of the Beast and flood the Nydus network with lava, but you can't do both.
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Savage Worlds: During character creation, plays are expected to choose between various "edges" and flaws that round out their character. The flaws impact what the characters can and cannot do, and are meant to actively interfere with their goals.
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Orcs Must Die 3 features this prominently in the Scramble Mode, wherein completion of each level lets the player pick one of two random handicaps and one of two random bonuses. By the time a player gets to the end of the mode the effects can radically change gameplay, from making all enemies immune to electrical damage but giving more money, to becoming immune to all slowdown and stunning effects but doubling the player's MP, to making traps far less effective but dramatically strengthening the player's attacks.
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Civilization: In Civilization V, the Fall of Rome scenario turns Culture and Social Policies against you if you're playing as Rome. To simulate the many factors that led to the decline of the Roman empire, the Roman policy tree contains only unhelpful policies such as Barbarian Conscription (-10% combat strength), Neglected Infrastructure (less Gold from city connections), and Popular Ennui (Luxury Resources provide less happiness). Though you can still choose which social policies to adopt as usual, policy skipping is disabled, meaning you must choose one every time you generate enough Culture for one. Oh, and did we mention you can't sell your Culture-producing buildings in this mode?
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Punishing: Gray Raven occasionally has an event mode called "Babel Tower" where, like Honkai above, you have to pick a number of handicaps that make your enemies tougher (by increasing their defense, attack or aggressiveness) or more annoying to deal with (such as them attracting you with a blackhole or planting small time-bombs on you when they hit you). The catch is that there are several levels and that the rewards depend on your combine score on all levels (but you can't use the same characters on two levels), meaning you can smooth out the difficulty by making each level only mildly difficult instead of making a single one super hard.
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Honkai Impact 3rd has a special mode called Elysian Realm, where instead of the usual 3-character team you pick a single character with two special support skills. The difficulty level is increased by choosing a number of special handicaps, which also increases the enemies' resistance as the level goes up. On the flipside, though, you also pick up special buffs on each floor, winch compensate for those handicaps if you combine them cleverly. Of course, the higher the difficulty, the more you are rewarded for clearing it.
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Shotgun King: The Final Checkmate: At the end of each level, you have to pick one of two sets of cards, which come with a card that upgrades your King and another that upgrades all the White pieces. While picking a black card that's very synergistic to your build is tempting, getting a bad combination of white cards can ruin your run as well. Hilariously enough, the end of the third floor will always give a White card that introduces the White Queen into the game, regardless of which set you pick.
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One random encounter in FTL: Faster Than Light is with a slug ship that will hack your choice of you Weapons, Shields or Oxygen systems, either turning them off completely, or if they are upgraded, merely weakening them. It is also possible to counter the hacking with your own hacking system, though that occupies the system, disabling it instead.
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Armello: During every Morning turn, the King presents the player who currently has the most Prestige points with a choice between two royal decrees, which usually (though not always) afflict the Prestige leader and/or every player on the board in negative ways, such as stripping them of resources or making NPC guards attack them until the start of the next turn.
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In Crusader Kings III, educating a child gives you events that will determine their core personality traits as an adult. If the kid is in your direct line of succession so they're likely to be your Player Character eventually, you may be stuck choosing between traits you'd rather not deal with, or the slightly better version of taking on stress to choose an alternative to the event's bad favored option.
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Darkwood: In addition to gaining a useful skill/passive when you level up, you're also forced to acquire a new weakness every few times as well, though depending on playstyle you can cushion if not outright ignore some of the weaknesses (e.g. taking “Shaky Hands” on a no-gun playthrough). However, you can choose not to level up and avoid both the positives and negatives, though as a whole the positive perks outweighs the cons.
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Gloomhaven: Before beginning most scenarios, players draw a road event card. The card describes a situation the mercenaries encounter on the road from the town to the location of the scenario, and provides two choices of how to deal with the situation. Frequently, both outcomes will be negative, though the catch is that players do not know exactly what way they will be impacted by each choice the first time they encounter a given road event. For example, if the road event is an encounter with a rampaging bear, players may fight it, which ends with the players starting the proper scenario with a wound that inflicts damage over time, or they may flee, tiring the mercenaries and forcing them to discard some ability cards, which also act as an indirect time limit.
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Frostpunk: In "The Fall of Winterhome" scenario, after you've fixed up the town and examine the generator that blew up and caused all the damage in the first place, your engineers tell you the generator is unfixable and won't last much longer until it completely shuts down, which kills your town's Hope meter. You'll have to set up a Citywide Evacuation, but you have two choices: tell the people you have no idea where they'll be going, which adds a permanent work efficiency penalty, or lie about another settlement they can go to and gain some Hope back. However, some of your engineers will catch on and will go and tell the truth, and you'll have to either kill them to uphold the lie or let the truth spill out and piss of the townspeople even more.
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Darkest Dungeon: The Final Boss's special attack, "Come Unto Your Maker", forces the player to choose who in the Player Party will suffer an instant, unavoidable One-Hit Kill.
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The Outer Worlds does this optionally with flaws, which you can choose gain as a side effect of in-game actions (for example, taking a lot of a particular chem gives you the option to become addicted to that chem). You're never forced to take a flaw, but doing so enables you to take an extra perk.
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StarCraft: A similar choice is given to you in the Terran campaign for Brood War. The mission before the assault on Korhal tasks you with destroying either Mengsk's Nuclear Silos or Physics Labs to cripple his nuclear arsenal or Battlecruiser fleet instead. However, the player isn't given time to destroy both, so they're more or less being asked whether they'd rather let Mengsk start the next mission with a massive nuclear arsenal or a fleet of late-game ships.
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Daggerfall: When creating a custom class in Daggerfall you may select from a list of advantages and disadvantages, such as critical weakness to disease, or a permanent ability to absorb magical attacks. How strong or weak the balance between advantages and disadvantages is will affect how quickly or slowly your character will level up. It is possible however to slightly cheat the system by choosing a race who is immune to one of the disadvantages in order to level up faster without the penalty affecting you.
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The Binding Of Isaac: Revelations: Shrine rooms spawn in the new floors added in this Game Mod, which contain two shrines that apply a handicap for the rest of the floor in exchange for an upside. You must pick one in order to open the door.
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Hades: Normally, the gods will give Zagreus different boons to choose from, but should he end up in Chaos' realm, he'll have to choose one of their curses to hamper him for the next 3-5 rooms. However, if you manage to survive the handicap, it'll turn into a boon and the negative effect disappears.
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XCOM 2: Every month, ADVENT begins preparing new "Dark Events" to make your life miserable in various ways, such as equipping all their soldiers with extra armor or placing Faceless infiltrators everywhere. To counter this, every month you can do a Guerilla Ops mission to stop one of these Dark Events to coming to fruition. However, you can't stop every Dark Event before it starts, so you will inevitably have to choose which Dark Events you'll just have to power through.
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The DEATH node in SUPERHOT: MIND CONTROL DELETE. Instead of giving you hacks to choose from between levels, the game instead makes you choose a basic gameplay function to give up instead. At first they're relatively minor functions such as GIVE UP JUMPING or GIVE UP THROWING. However, you'll eventually be asked whether to give up things like shooting or punching. By the time you've given up moving and looking, you're totally helpless. The only option left... is to simply GIVE UP.
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Revita: With the "Cursed Choice" upgrade, whenever you would be inflicted with a curse, you get to choose between two of them instead of it being chosen for you randomly. Can be indispensable on runs with high Lucent Shard counts, as they can come with modifiers that make more relics corrupted or even make you start the run with them.
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Yuppie Psycho: When bitten by a White Snake, a dialogue box will pop up with Mr. Devil asking where the creature bit you. Whatever body part you choose will be disabled; choosing your nose makes it harder to breathe underwater, choosing mouth disables healing items, choosing ears turns off sound, and so on.
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In Goddess of Victory: NIKKE's Simulation Room, one of the possible events you can get is Worst Case Scenario, in which you are forced to either lose some of your buffs, lose some of your characters, or force every character in your roster to take 40% damage.
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Game Tropes
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Video Game Difficulty Tropes
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 Armello (Video Game) / int_33d0ba5d
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 Civilization (Video Game) / int_33d0ba5d
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 Crusader Kings III (Video Game) / int_33d0ba5d
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 Darkwood (Video Game) / int_33d0ba5d
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 Dicey Dungeons (Video Game) / int_33d0ba5d
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 FTL: Faster Than Light (Video Game) / int_33d0ba5d
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 Hades (Video Game) / int_33d0ba5d
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 Honkai: Star Rail (Video Game) / int_33d0ba5d
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 neonâ�–Knights (Video Game) / int_33d0ba5d
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 Punishing: Gray Raven (Video Game) / int_33d0ba5d
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 Revita (Video Game) / int_33d0ba5d
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 Shotgun King: The Final Checkmate (Video Game) / int_33d0ba5d
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 StarCraft (Video Game) / int_33d0ba5d
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 StarCraft II: Wings of Liberty (Video Game) / int_33d0ba5d
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 Superhot (Video Game) / int_33d0ba5d
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 XCOM 2 (Video Game) / int_33d0ba5d
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