You were a member of an outlaw band. You might have been part of a troop of cutthroat bandits, or a resistance movement battling a tyrant, or a pirate fleet. You lived outside of settled lands, and your name was a terror to rich travelers.

How did you join your outlaw band? Why did you leave it—or did you?

You lived for years alone in a remote shrine, cave, monastery, or elsewhere away from the world. Among your daily tasks you had lots of time for introspection. 

Why were you alone? Were you performing penance? In exile or hiding? Tending a shrine or holy spot? Grieving? 

It never hurts to be part of a team, and when you’re part of a guild opportunities knock at your door.

Are you a member of a trade or artisan’s guild? Or an order of mages or monster hunters? Or have you found entry into a secretive guild of thieves or assassins?

Whether you worked as a sentry, constable, member of the city watch, or even a knightly order, rich folk used to pay you to protect them. These days you’re looking after yourself. 

Did you stand watch in a throne room or lookout tower? Walk a beat on city streets? Travel with a caravan? Why did you turn in your badge and sword?

You haven’t met your match at dice or cards. A career of high stakes and daring escapades has taught you when to play close to the chest and when to risk it all—but you haven’t yet learned when to walk away.

Are you a brilliant student of the game, a charming master of the bluff and counterbluff, or a cheater with fast hands? What turned you to a life of adventure: a string of bad luck, or an insatiable thirst for risk?

You were born to a commoner family, but some event earned you fame. You’re admired locally, and tales of your deeds have reached the far corners of the world.

Did you win your fame by battling an oppressive tyrant? Saving your village from a monster? Or by something more prosaic like winning a wrestling bout or a pie-eating contest?

You were raised a farmer, an occupation where the money is short and the work days are long. You’ve become an adventurer, a career where the money is plentiful but your days—if you’re not careful—may be all too short.

Why did you beat your plowshare into a sword? Do you seek adventure, excitement, or revenge? Do you leave behind a thriving farmstead or a smoking ruin?

Your homeland is barred to you and you wander strange lands. You will never be mistaken for a local but you find ready acceptance among other adventurers, many of which are as rootless as you are.

Are you a banished noble? A refugee from war or from an undead uprising? A dissident or a criminal on the run? Or a stranded traveler from an unreachable distant land?

You’re a performer who knows how to dazzle a crowd, an artist but also a professional: you never forget to pass the hat after a show.

Are you a lute-strumming singer? An actor? A poet or author? A tumbler or juggler? Are you a rising talent, or a star with an established following?

Ability Score Increases: +1 to Charisma and one other ability score. 

You were a member of a sinister cult. You performed ancient rites found in forbidden tomes, seeking to empower a fiend, a false god, or a terrible being from a strange and distant realm. 

Why did you leave the cult? Did you come to recognize the emptiness of its promises of power? Did you witness horrors that shook your faith? Or do you still nurture its dark edicts in your heart?