I'm a person with a career, and I don't waste my time trying to figure out how to outsmart other people. (I don't think I could anyway.) I don't know about you, but solving the actual problems I encounter at work (problems which are obviously not attributable to people) are enough for me!
(Obviously I don't know the nature of your job exactly - this is from the perspective of a typical tech employee).
People gain self-esteem in many different ways. Sad as it is, the teacher's last ditch warning to the uncaught cheater "you are only fooling yourself" does not necessarily work on the type of person who is inclined to cheat. It's quite possible the Hatton garden thieves, having liberated a lot of property from what they would consider the underserving rich, felt absolutely GREAT about themselves. They were caught due to boasting about the crime after all.
For someone who sees law as essentially a social, artificial construct (who hasn't internalized this notion), every career is about outsmarting others anyway, in one way or another.