Jenn grew up hard on the streets. Stubborn, independent, and quick were the best words used to describe her. Her father was a sewer "cleaner" who met his end while working (she doesn't know any more than that, except that one of his old mates told her it "wasn't pretty"). Her mother was a maid, and did her best by the child, but was often at work and thus Jenn had to fend for herself as often as not. She always had a good streak, but fell in with a gang for a time, where she first learned the tricks of her eventual trade. By age 10, she was one of the best scouts the Crickets had, her slight size and relative youth lending an air of authenticity to her claims that she was lost, if she happened to get caught.
Being a scout meant that she had to travel lightly, and could not appear to be armed or wearing armor (even if she could have afforded any), so Twice-Done, the Crickets' leader, saw to it that her training focused on easily hidden smaller blades, and that she learned quickly how to get out of the way of things coming at her. This continued on over time, and she was soon known as a fair hand with a knife or dagger, much to the chagrin of the older boys who now saw the teenage Jenn in a different way...
Her mother, Maira, saw all of this happening and was frustrated, but also was not around enough to put a stop to it. So she took Jenn aside one night and had a long talk with her, in which she told her that it was good that she had friends, and even better that she was looking after them, but asked if Jenn really felt that these were people she could trust, especially if something went wrong.
This got Jenn thinking, and looking. Really looking, for the first time in a while. She came to the realization that she did not believe the Crickets would be there for her if something went sideways. She also didn't believe they'd just let her walk away. It was while she was considering how to get out that things went sideways, in a way she was not prepared for.
The estate of Lord Grinstead, where her mother worked, was hit by a rival gang, the Busted Knuckles, and Maira was killed during the robbery, the victim of an errant slash between a guard and a thief. Jenn was informed later, when her mother didn't come home and she went to the Lord's estate to ask after her. The news broke her. She felt like she no longer had an anchor, no hope for her future. No one to love unconditionally.
The next morning, with no more than the clothes on her back and a knife hidden in her waistband, she made her way to the drill yards for the local militia, and volunteered to join. After the recruiting sergeant got done laughing at a 16 year old girl wanting to serve, he sent her away. Jenn left, then snuck into the militia camp. She kept an eye on the old sergeant, eventually following him to his tent. Waiting until he was gone again, she left a note on his cot that read, "You should have taken me. I got past your guards and made it here, then left again. Change your mind. I will be back tomorrow."
When she arrived the next day, she approached the sergeant and said, "Get my note?" He gave her a long, hard look, then nodded once. With that, Jenn became a member of the militia. A month of basic training, where Jenn demonstrated her scouting skills and ability with a knife, and she was given a scout's uniform, some leather armor, a cot in the barracks tent, and three hot meals a day. She received training in basic drill, skirmishing, and (most interestingly, to her) the shortbow.
While on an afternoon pass, she went back into the city and located one of her former mates, Shen. Shen saw the uniform and did a double-take, but ultimately agreed to let the other Crickets know that she was militia now. As they parted, Shen told her that he hoped he wouldn't have to fight her in the future. One hand on her knife, she said, "Me too, but if I do, I'll make it quick."
She served for three years without incident, gaining some experience and being involved in goblin raids, border skirmishes, and bandit battles. When her three years were up, she chose to leave rather than re-up, and set out on her own. Now, nearly 20, she moves from place to place, looking for work that will allow her to utilize her skills but not compromise her morals...
