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Merriam - Webster Dictionary defines the term “Look over your shoulder” as….
idiom. : to worry or think about the possibility that something bad might happen, that someone will try to cause harm, etc. You have to be looking over your shoulder in this business.
https://www.merriam-webster.com › …
 
But as you can see by the brilliant artist Qrcky’s painting by the same name looking over your shoulder means reflecting about what you’ve been through while preparing for the future. Look at this amazingly beautiful paint of this proud and distinguished black man facing forward, while looking over his shoulder. He’s not worried, he’s ready ! He’s know his future is going to be wonderful but will also take a lot of work. Just as it had taken a lot of work to get to the current point in his life…