Kidnapped soon after birth, you were raised in a hidden monastery to become an assassin. Killing has been your life for as long as you can remember. You trained as a youth, studied the use of weapons and armor, learned basic survival techniques. While you've associated with many thieves and pickpockets, your skills are far more... specialised. You managed to escape the monastery that kidnapped you, and you now go about your general life (though you sleep with one eye open).

When you choose this background, work with your DM to determine which Assassin's organization you were a part of, how far through its ranks you progressed, and what kind of experiences you had during your career as an assassin. 

Skill Proficiencies: Choose one proficiency from the following options: Deception, Intimidation, Persuasion 

Choose a second proficiency from the following options: Sleight of Hand, Stealth, Insight, Perception, Survival

Tool Proficiencies: One type of gaming set, thieves’ tools

Equipment:

A bedroll and a crossbow, a set of dark common clothes including a hood, and a pouch containing 15 gp

 

Suggested Characteristics

Assassin Monk escapee's live with the constant fear of their prior organization catching up with them, often making them seem somewhat unpredictable. The horrors of their history combined with the twisted structure of the assassin's organization leave their mark on all escapee's, often leaving them with a black and white view of the world.

d8	Personality Trait
1	I always have a plan for what to do when things go wrong.
2	I am always calm, no matter what the situation. I never raise my voice or let my emotions control me.
3	The first thing I do in a new place is note the exits or escape routes - or those areas that could act as one in a pinch.
4	I would rather make a new friend than a new enemy.
5	I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
6	I will always carry out my task with a dogged determination.
7	The best way to get me to do something is to tell me I can’t do it.
8	I blow up at the slightest insult.

d6	Ideal
1	Honor. I do not kill good men, or men of faith. (Lawful)
2	Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3	Charity. I will kill to protect people who are suppressed. (Good)
4	Greed. I will do whatever it takes to become wealthy. (Evil)
5	People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down the Styx for all I care. (Neutral)
6	Redemption. There’s a spark of good in everyone outside of the organisation. (Good)

d6	Bond
1	I owe my life to an old friend, one day they will call in that debt.
2	I will find my sibling, they fled the organisation before I did.
3	My childhood was taken from me. I will found out where I came from.
4	I will become the greatest assassin that ever lived.
5	I’m guilty of a terrible crime. I hope I can redeem myself for it.
6	Someone I loved died because of I mistake I made. That will never happen again.

d6	Flaw
1	When I see someone evil, I can’t think about anything but how to kill them.
2	When presented with an opportunity to kill an old member of the organisation, I will take it, no matter what.
3	If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
4	I have a “tell” that reveals when I’m lying.
5	I act first, talk later. It's the fastest way to move on.
6	An innocent person is in prison for a crime that I committed. I’m okay with that.