You get

A very short bow, muddy shoes, a bottle of deer urine.

Why have you quit?

1. Cursed: A gigantic blue elk with golden glowing eyes approached as you took your final catch, promising to hunt you to the end of your days if you stepped foot into its forest again.
2. Hunting Accident: Your younger sibling would invite you hunting every time your parent spoke of passing down the family’s wealth onto you. You got the message with the last crossbow bolt that narrowly missed your head, and have disclaimed your inheritance.
3. Broken Heart: After your old blood hound couldn’t follow you on any more hunts, you felt it wasn’t
4. Nobles: All of the lords decried the forests of the land their own person domain, forbidding any others to hunt within, putting you out of a job.
5. Wizardslaughter: You didn’t mean to kill the village’s most-loved and kindest-hearted wizened old sage. You had no idea they polymorphed themselves into wildlife to go frolic in the woods.
6. Haunting: The dooming blight that has choked many lands has reached your ranges, littering the once peaceful groves with hungry ghosts.

What keepsake did you retain?

1. Worm-Calling Whistle: High-pitched whistle that attracts around a dozen earthworms, grubs, and other dirt-crawling beasts when blown.
2. False Boomerang: This heavily-weathered boomerang not only does not return to you, but seems to travel unerringly in a straight line forever until it crashes into something. You’ve been worried you’re going to lose it if you throw it towards the sky.
3. Bear Suit: The entire furs of a person-sized bear, treated and stitched to be wearable. Its a bit hard to see out of the beast’s snout, but not the worst disguise from afar. On a foggy day. While situated amongst the brush. When trying to hide from someone with poor vision.
4. Game Spookers: A very weighty round brass bell. Toss into a bush to scare out any game, or to dangle upon your walking stick to give yourself your own entrance music.
5. Snare Kit: A heavy canvas sack filled with all manner of traps – iron teeth, lassos, ropes, nets, counter weights, snares, etc.
6. Salts & Spices: A very fine wooden box filled with tubes and pouches of uncommon spices, treating salts, fancy woods. Suitable for preserving small game or adding a bit of pizazz to a campfire meal.

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You get

Austere robes, book critiquing a rare field of study, ink-stained fingers.

What ended your studies?

1. Tuition: After an adventuring crew wrecked the local economy, prices at the academy have been steadily rising. You were not able to pay last semester’s rates, but maybe if you could find the elf crypt those adventurers were whispering about…
2. Forbidden Studies: Your latest term paper startled the whole faculty. The model of the metaverse you presented lorded over by about a half-dozen capricious deities literally playing dice with the universe got you immediately expelled.
3. Bullying: Stuffed into a locker for the last time, you have decided to find a magic item to prove to your ruffian classmates that you have more mettle than they believed.
4. Academic Cult: Staying late in the library one night, you heard a commotion in the commons and tip-toed to check it out. The entire faculty was surrounding a horrific obsidian idol, and they removed their faces, revealing themselves to be some kind of worm or centipede creatures posing as teachers.
5. Doppelganger: A alchemical experiment gave life to an evil twin of yourself. The academy only had room for one student though, and your doppelganger made quick friends with your friends and teachers, and they decided that it would remain in your place. The final straw was when you returned home and your parents were feeding and bonding with the clone.
6. Lack of Languages: Despite your best efforts, you just haven’t been able to speak the dozens of fantastical creature and planar-being languages. Maybe if you encountered them in an environment outside of the classroom you could catch up.

What was something you never returned to your academy’s tower before leaving?

1. Technicality Imp: Former familiar of one of your teachers, this annoying little creature always corrects people with the most specific interpretation of topics discussed.
2. Cypher Satchel: Shoulder bag that jostles letters around in any book contained within. Normal books are reduced to incoherent messes. When a jumbled book is placed back into the satchel and shaken around the letters return to their normal position.
3. Inverted Chalk: A stick of chalk that consumes writing instead of producing it.
4. History of Known Traps: While not going into the mechanical workings of any particular traps, this tome describes the history, trends, and authors of a variety of known dungeon hazards.
5. Monocle of Dust and Mites: A single lens that reveals the precise quantities of dust in the nearby environs, as well as allowing the wearer to peer into the secret lives of the microscopic goblins that dirty all our things. Everything else viewed with this monocle on is indecipherably blurry.
6. Blood Dowsing Rod: Creepy forked stick that points to the largest source of blood in a thirty-foot area.

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You get

A net, a dark handkerchief, a board with a spike through it.

Why did you stop smuggling?

1. Pursued: A paladin of the lawful deities of economies & trade swore an oath to see you apprehended. Fortunately they are still tied up getting the correct permits to come after you, but you fear the day they get their paperwork in order.
2. Unnatural Encounter: Delivering trinkets to shadowy cove, your patron revealed itself to be a tentacled thinking fish who psychically monologued about drenching the surface to return the planet to the control of a oceanic empire.
3. Blackmailed: The local rogue’s guild threatened to go directly to the Bishop, your uncle with proof that you have been delivering relics to the cults of chaos. They now demand you seek out treasures for them.
4. Revenge: Appalled to discover that the “rare heirloom bottles” the dark-robed figures had you trek back and forth between coteries contained the spirits of the deceased, you swore an promise to free any remaining soul part-damned by your deeds.
5. Catastrophe: Your entire supply was sunk deep under waters, the duke you were delivering it to demands you pay, and a population of clamfolk are infuriated at the pollution you caused.
6. Addicted: Having made it big smuggling a very rare myconid growth to rich merchants of the port cities, you tried to sample just one brewing of mushroom tea. The other realms of existence it revealed to you was so intoxicating, but the price of a single serving so high that you knew you had to get as far away as possible.

What’s one item that “fell off of the wagon”?

1. Frost Giant’s Spit: A bottle of azure liquid that stays exceedingly cold, can temporarily freeze anything it is poured upon. Enough fluid remains to coat a hypothetical forearm.
2. Dark Creeper’s Night Soil: This bag of foul smelling fertilizer can cause seeds or bulbs to full grow within 24 hours. You really hope the name is just a joke.
3. Insurrectionist Doom Tablets: Clay tablets pressed with worrying amount of praise to the dark gods, coupled with some really good criticisms of the exploitation done by nobles and clergy.
4. Displacer Beetles: Tiny box filled with beetles that are always closer or further than they appear.
5. Faulty Holy Symbols: A bunch of vampires were trying to circulate holy symbols that would fail mid-turning among the clerical order. You have about a dozen of these.
6. Shrieker’s Treat: One vial of a particularly nasty poison that forces its victim to continually scream until passing out and potentially suffering permanent brain damage.

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You get

One nasty dagger, a pouch full of buttons, a tooth pick.

How were you caught?

1. Lack of Finesse: Turns out walking right up to someone, holding direct eye contact, and shoving your hands straight into their pockets and purses is a great way to be immediately arrested.
2. Mini Man Alarm: Bit by a pocket homunculus, your yelps gave you away.
3. Outplayed: Your last mark was a master counter-thief, every pence you thought you took from them somehow ended with every last thing you owned being transferred to them.
4. Betrayed: One of your companions pointed you out to the sheriff, who used your capture as a feather in their cap.
5. Loud Mouthed: After buying several rounds of ales, a stranger asked you how you came upon such good fortunes. You quickly learned that honesty is not always the best policy.
6. Divination: After retiring from a career of adventuring, the local hedge mage decided to become a village detective.

What was the oddest thing you lifted?

1. Tiny Totem of Confidence: A figure of a local deity carved from smooth stone, when it belly is rubbed you can hear affirmations in your head.
2. Digestible Treasure: One purse full of imitation coins, the gold nothing but foil. The chocolate internals at least is a rare treat.
3. Psychedelic Mold: The leather purse your stole from a visiting druid contained only patches of moist growth inside. Ingesting this made you acutely aware of the secret lives of colors and the varies polyhedral shapes living in-between wood grains.
4. Pouch of Devouring: Fanged on the inside, this bag whines if not provided with a weekly meal. Seemingly able to digest all sorts of organic and inorganic material you can it into it without producing waste. Or at least, without producing waste as of yet.
5. Monster Teeth: Unsettlingly, the local miller had a purse practically bursting with a variety of fangs, teeth, and claws. You are unsure if you should report them to someone, or if you can use these in some kind of ritual.
6. Lovely Lich’s Locket: Unsure who it belonged to, but someone in your village kept a heart-shaped locket with a rendition of the Dread Lich Pestulentia. Can you use this to your advantage?

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You Get

A dramatic outfit, a set of makeup, a withered rose.

What was your final performance?

1. Avant-garde: You experimental one-person-show perplexed even the most diabolical coalition of warlocks who cursed you to never play again.
2. Offensive: The prince did not enjoy the laughter of the crowd responding to your musical accusations of his romantic failings.
3. Injury: The exotic beast seller promised you that your purchased owlbear was toothless. Turns out beaks are just as deadly.
4. Maddening: A travelling astronomer pitched you a sheet music inspired by vibrations they claimed to hear while looking into the night sky. Your fluting rendered the audience into a gibbering, howling state, rasping in fear and admiration of something called “the dwellers beyond the veil of space.” Not exactly your theater’s name so you didn’t take it as praise.
5. Timidity: Your one and only performance involved you staring wide-eyed into the audience for several minutes. When you finally opened your mouth to speak your lines you were caught in anxiety-induced dry heaving. Everyone uncomfortable got up and just walked out.
6. Cursed: The various poems you recited mocked all variety of unnatural beings and their believers as delusional. A wayward godling found your atheism disquieting and cursed you to be a magnet for the supernatural.

You made off with this trinket from your troupe:

1. Simian Skull: Sometimes confused for monster bones, this fanged skull smells faintly of exotic fruits.
2. Massive Prop Weapon: A gnarly blade resembling one of the many gods’ weapons, much more intimidating until its revealed to be a wood-and-wool replica.
3. Speculative Future Clothing: A peculiar cotton t-shaped tunic, and rough blue trousers with a peculiar buckling apparatus near the front of the waist. This outfit is based on a fictional codex of time traveling serf to the far futures.
4. Tome of Troubling Limericks: These verses become less bawdy the further into the book you get, and become more and more harrowing.
5. Many Faced Mask: This leather and plaster mask appears mundane, but every time it is slipped off it takes the countenance of a random creature of legend.
6. Stage Double: Seeing as how you are out of work, your double also is. They continue to follow you day to day, but not without regularly complaining that you ruined their career.

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You get

A green tunic marked by a few holes, a painted wooden pence, a threatening short bow.

What ended your run from the law?

1. Snitching: You reported on fellow scoundrels out-of-law. Your name was cleared, but you made a few enemies.
2. Humiliated: You were captured, put into the stockades, and the whole town got a good laugh by throwing rotten food and eggs at you for a week. Now the urchins point and laugh, calling you Stinky Salad.
3. Conscience: The first time you tried to grift or rob anything a small child looked at you in shame, you have since recanted your ways, fearing the gaze of the innocent.
4. Remuneration: You turned yourself in, and were fined everything you own. Routinely you witness the Baron’s snotty son misusing your former prized possessions.
5. Loophole: Turns out your crimes were not really crimes. You spent all the time living off the land, so you need to make the oncoming years count, and everyone feels a ton of pity for you.
6. Betrayal: You strolled into the town and pinned and made a bold-faced lie that you were framed. Nobody really liked the miller who suffered the wrath of your pointed finger, but many say his daughter has declared revenge upon you.

What weird trinket did you stumble upon on your journeys?

1. Eternal Hat: The hat you wear upon your head always produces a new hat underneath when you take the previous one off. Every hat is distasteful and out of style. You haven’t figured out how to bare your head since putting the initial hat on. None of the removed hats retain this odd affect.
2. Comedic Apple: This piece of fruit won’t stop telling groan-worthy jokes and puns that barely work. You think your companions are going to eat it out of annoyance.
3. A Very Stupid Parrot: This gorgeous bird is willing to follow commands, but always misinterprets them in astonishingly bad ways.
4. Fireworks: You stole a crate of very moldy fireworks off of a wagon. Somewhere less than half a dozen still function, although not predictably.
5. Lasso of Fibs: When bound by this rope, the victim may not say anything that is true.
6. Tin Can of Partial Message: A single word may be shouted into this tin can, and then next time someone holds it up to their ear, they hear it. Its also very strict about compound words and you almost feel like its judging you when “strawberry” gets repeated as only “berry.”

This work is licensed under a Creative Commons Attribution 4.0 International License.

You get

A nice floppy hat, a pouch of spices you accidentally mixed together, a small club you used to chase away thieves and savvy hagglers.

How was your career ruined?

1. Ridiculous inventory – Turns out very few people are interested in purchasing “The deed to 1 Goblin.”
2. Cursed product – That weird sky rock you sold to the baron cracked, besetting the fief with vapors of an intelligible color. You decided to skip town before anyone traced the source.
3. Lost investment – The spice ship you paid for almost reached the Duchy before it was wrecked by the marauding merfolk. If only you had coin enough to hire muscle to go retrieve the wreckage.
4. Limitless discount – Your initial idea of giving someone a coupon redeemable for 10% off of a purchase for ever 100 gold pieces spent drew lots of return customers. Then someone had the bright idea to cash in 10 at once and take everything.
5. Hunted – Your specialty of monster teeth and claws came back to bite you in more ways than one when a troll regenerated from a poorly bleached fang.
6. Planar legal fees – Thinking this nasty-looking silver sword you were traded by an adventurer would net you a pretty penny, you were met with headache when a strange-looking figure stepped out of a portal threatening legal action as your “crystal sphere” didn’t have the license associated with selling such a weapon.

What was one interesting trade that you kept?

1. Riddle Skull – A human skull that responds to the words “riddle me” with a unique riddle, up to once per day. Getting the riddle wrong enrages the skull who spends the better part of an hour trying to bite you. You were told something great would happen if you got three days in a row correct, but have yet to do so.
2. Rodent Automata – Brass and tin mechanical mouse. Will follow instructions of up to four or five sentences spoken to it before being wound up. Afterwards it will buzz and hum and go about completing the task, best it can as a small, robotic mouse. Unfortunately its winding only sustains it for about ten minutes.
3. Wand of Clutter – Gesturing this wand at a sorted collection of dishware, clothing, or any nick-knacks will compel the items to get up, run around in disarray and come to rest in a mess over a 10 foot by 10 foot area.
4. Tricorn of True North – A decent hat that will rotate atop your dome, always pointing north when worn.
5. Iridescent Salamander – Small lizard-like creature that secretes a lightly-glowing fluid once a day when agitated. This substance glows with about the luminance of a candle and glows in a variety of colors. The salamander unfortunately also bites when angered.
6. Man’s Best Boot – This single leather boot follows you with the upmost loyalty and even pants like a dog. It isn’t able to bark, but will excitedly tap or stomp the ground.

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You get

Gambeson reeking of body odor, a spear with a notched shaft, one stale sausage.

What is your shame?

1. Fired: Your routine shirking of duties, going AWOL, and just plain ornery nature led to you getting kicked out of the company. Everyone but one of your old sympathetic pals look down upon you.
2. Shell-shocked: Your crew was one of the first to acquire a prototype canon. Not completely sure how it worked, they launched you from it. You now reek of gunpowder no matter how much you wash.
3. Snitched On: The blink dogs that your mercenary group used as scouts saw you stealing a bit of extra from the company’s coffers, and dutifully did their best Lassie impression to point you out. Despite being thrown out, one still pursues you to this day.
4. Last Mercenary Standing: You were ordered to slay one man in a set of ruins. The figure transformed before your eyes, taking the shape of a massive minotaur, brutally slaying your friends. Somehow you were hidden in the rubble and the gore and were survived, but swore vengeance upon this shape shifter.
5. Laughing Stock: Your preference for ridiculous and sometime self-injuring weapons such as massive flails, impractical whips, chain staves, and the like got you laughed at by all your companions. You decided to wander off, the lone wolf that you are, to prove to them that your prototype boomerang-crossbow will be the next advancement in warfare.
6. Undead: Your previous mission to the Crypt of the Dread Necromancer ended, unexpectedly, with your gruesome death. What was surprising, however, was that your arose that very night, a member of the unliving. Aside from stinking a bit and being unable to bear the sight of holy symbols you seem to be mostly the same. You feared persecution and decided to flee from your company.

What treasure did you find on your final mission?

1. Sarcastic Suit of Armor: You found a set of pretty decent plate, but it seems to be related those fabled singing swords as it always has some disparaging remark or joke about whatever your doing. This is especially annoying because whenever it talks it flaps its visor up and down, even while you’re wearing it.
2. Rodent of Radiant Charisma: While marching through the marshlands you fell under the enchanting spell of a capybara. This creature seems to have a calming effect on most mundane animals when not too much of a commotion is going on.
3. Handgonne: An extremely rare metal tube set into a heavy block, if you stuff this full of blackpowder and a variety of sharp or metallic objects, you’re able to produce an extremely dangerous blast. Sometimes that danger affects you and your friends. You weren’t fortunate enough to discover a user’s manual as well.
4. Reverse Umbrella: You drew the shortest straw so all of your companions got first pick of the (murdered) wizard’s armory. This is an umbrella that produces a localized rainstorm when its open, pouring continuously out of the umbrella.
5. A Really Opulent Hat: Full of feathers, pins, adornments this massive hat is always the center of conversation.
6. Harpy Egg: Everyone told you not to take it. Anger the harpies they said. You’d be the death of us they said. Well turns out they were right, but that’s not gonna stop you from being a momma soon.

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You get

A heavily knotted rope, a hooked push pole.

Why is it hard to get you to step on a boat?

1. Abandonment: The deal you made with the merfolk to marry one of their own in exchange for sea-riches turned out to be a double disaster – the riches was just a decade supply of pungent kelp, and your betrothed was a ravenous deep one. Leaving a fish beast at the alter is slight the sea shan’t soon forgive.
2. Disfigurement: Deciding that two peg legs are enough, you’ll try your lot on land.
3. Fired: Your cantankerous shanties were decreed a nuisance, and your constant chugging of rum despite your penchant for sea sickness had fired from your position on the ship – literally, as your captain stuffed you into the cannon and launched you onto the nearest shore.
4. Cursed: Ever since you decided to use gulls as target practice you’ve felt that the sea itself had it out for you. Constantly toss overboard by storm, harassed by sharks, even once an octopus climbed aboard simply to attempt strangling you, you feel keeping your distance from water is for the best.
5. Jonahesque: Your ship smashed and you swallowed whole by a leviathan, you became accustomed to the horrors of the dark as you traversed the belly of the beast. Only by joining a party of a wood golem, a miniature thri-keen and a wizened craftsman were you able to make your escape.
6. Change: You just found yourself tired of the constant rocking of waves, fish, and the salty air, you decided stable ground would be far more adventurous than long months on a urchin-crusted vessel.

What memento do you carry with you?

1. Clam of Devouring: A small mollusk with a serious appetite, this shelled creature will clamp down on anything you it can get its shell around. It will then, extremely slowly, begin to digest whatever it has caught.
2. Sea Monkey: Despite appearing as a flask of salt-water, when splashed the watery contents transforms into an only moderately-disobedient monkey, who desperately doesn’t not want to be reconfined to its vessel.
3. Boat Terrorizing Flag: A black flag you stole off of a notorious pirate ship, this flag allows you to turn boats as a cleric turns undead.
4. Eye-Patch of Night Seeing: This mystical eyepiece gifts you minor low-light vision, at the cost of your depth-perception.
5. Land Remora: Not entirely clear how this fish survives outside of water, this being wriggles all around your body nibbling at crumbs, flakes of dried skin, loose threads that you have.
6. First Mate: A not particularly bright sailor from your marine days follows you around as long as they are fed, providing low quality manual labor and high quality commentary on all of your mistakes.

Inspired by Electric Bastionland, Knave, and Ten Foot Polemic.

This work is licensed under a Creative Commons Attribution 4.0 International License.