To know ones way around, is a phrase regarding a person who is street wise and is used to the everyday ups and downs of life in a particular town or dirty. Someone who has the experience to tackle any kind of challenge  in everyday Life...in other words a hustler. 

Working your way up is somebody who works himself/herself up the corporate ladder from the ground up, from the basics, lower level and income to the highest level of the job. It could also describe a social climber who has an iffy background from a working class background and become involved with richer more established folks.