"[3] After leaving school at fifteen, Cheechoo experienced problems with substance abuse, but eventually, she turned her life around and began to work in film and theatre to explore themes of healing and survivance post-trauma.

Her experiences at a residential school and her road to healing are documented in her stage play 1991 Path with No Moccasins.

Shirley is the first First Nations woman to "write, produce, direct, and act in a feature length film from Canada".

Path With No Moccasins gave Shirley the opportunity to "speak about her life and the struggle to retain her identity, and Cree heritage".

[9] Silent Tears chronicles the events of a "harsh winter trip with her parents to a northern trap line when she was eight years old".

[9] In order to promote Aboriginal artists, Shirley and Blake Debassige co-own Kasheese Studios art gallery.

Anything in the arts gives these kids a lot of self-esteem ... the arts are really important for children and they're not taught in the schoolsShirley is concerned with Indigenous people's complacency with "small advancements and the slight changes that appear when it comes to equality and respect" and believes that "We must continue to fight in the most positive way to try and find a level playing field for Indigenous people to work, live, and create in the main".