Debbie: Yeah, he's totally waldo.
A person that generally has a plan for everything.
Also a character in a book Titled Wheres Waldo, where you must find waldo hidden between a group of people.
I can't believe that your leaving the company on such bad terms.
In this case, "your" should actually be "you're" to be grammatically correct.
Also see waldoing and dickbagging
Guy2;That's Bryce he's a total Waldo
Guy1;What a dickbag