Kaylen has had a hard life from the start. Born to a pillow-girl in the slums of Korvosa, she was on the streets by age 3. She fell in with a street gang to survive. She didn't like it, but it kept her fed and alive. The first lesson she learned was that the streets didn't care who you were, and that if you wanted to survive you had to be tough. She taught herself to fight, and she learned to hide that she was a girl. When the boys in her gang and in others saw that she was a girl, they always treated her differently. She made sure they didn't make that mistake. As she grew, she became the best fighter in her gang, and one of the best fighters among all the street children. Her weapon of choice was something she found on the street when she was 7. It was a length of chain with weights on the end. She taught herself how to use it to smash opponents at range and to wrap the end around them to drag them closer.
When Kaylen was 12 or so, she entered the annual children's street tournament. The tournament was a fighting competition, and the winner earned a spot in the Korvosan Guard Academy. Kaylen entered the tournament in her guise as a boy. She won the tournament, earning the spot in the Academy. She kept her guise as a boy, not wanting to be treated differently because she was a woman. She managed to keep that guise for two years until her womanhood forced itself upon her. She was released from the Academy, pending a hearing, for having lied about who she was. She was permitted to keep her gear, but she was not to join any military or guard corps until after her fate was decided in seven years time.
That event was two years ago. In the interval, Kaylen has made her way as a mercenary. She has been a bodyguard, a caravan guard, and hired muscle. In the two years that she's been waiting for things at the Korvosan Guard Academy to be decided, she has made her way to Riddleport. Now she is looking for a long-term guard position where she might wait out the remainder of her sentence.