Someone who always makes bad decisions and finds trouble or is born into a hardship that puts them into a troubled existence, but then manages to find a way to rid his/her life of said trouble. Therefore, becoming untroubleless.
After doing his time and spending 8 years in prison Bryan got out and met up with his homie Pedro and emphatically declared, "I'm untroubleless for life!"
by King Vicious March 05, 2019