Why Is Expertise a Trap?

Nick Kokonas says expertise is a trap because comfort is how you get passed. Once the money is good and you know the work, a younger person with fresher eyes will break the convention you now defend. The expert is the target. The move is to quit before that happens and go find the next thing, even though quitting gets slower with age and a success makes it expensive to start over and lose money for a while.

He keeps a small figure of Sisyphus on his desk, the same kind of object his father kept. The push is the work. He had left the restaurant business, then walked past an empty space and felt the pull to build a wine bar. Everything in him said not to do it. That was the reason to do it. In this telling, the work is the win, and the man pushing the boulder is where he wants to be.