Bounty Board

You decide that you might want to go the "assassin" route. Taking down an escaped fugitive might be a good place to start and build a name for yourself. Outside the tavern the board is easily found.

Looking down the list of jobs several peak your interest:

Bandit King Jack

A local bandit who is attacking travelers on the road. Level of Difficulty: Normal

Dread Pirate Morgan

A pirate who is believed to be hiding out nearby. Level of Difficulty: Hard

Pickpocket Flynn

A simple pickpocket. Level of Difficulty: Very Easy

Nightingale

A rumored individual that is either a spy or leader of the Thieves' Guild. Identify is unknown. Level of Difficulty: Very Hard

Further down there are other bounties.