Making a u-turn

Can people backtrack? If someone were to be button-down, do things by the book because it's the right thing to do, is it possible to step away from that without being overwhelmed by guilt? My mind says, yes, out of the grace and mercy of our Lord Jesus Christ. Why is it hard to do? Maybe, if the person were to worry more about what others think about him, it would be hard. Has anyone ever done a large about face with regards to a major life issue? If so, what did you learn and notice as you walked through this experience?