Jim Halpert’s problem on The Office is that he’s addicted to detaching.
While Jim may have a great sense of humor and an insight that sees right through his coworkers, he’s notably less perceptive about himself. His ironic above-it-all-mentality and fear of engaging make him an observer who’s stuck on the sidelines of his own life.
He spends years miserable because he won’t go for the things he wants (like Pam, or a job he actually cares about.) He constantly mocks everyone else, yet he’s so afraid of being ridiculed himself that he won’t even dress up properly for Halloween or do anything that might bring him embarrassment or scrutiny.
Jim’s happy ending is finally overcoming his impulse to withdraw, observe and detach.
He embodies the overarching ethos of The Office: through learning to love and engage with the people around him as equals—instead of just observing them with judgement—he finally learns to love himself.
(The whole ‘buying a secret house and getting a secret job’ thing is still really weird, but you didn’t hear that from us…)