Short synopsis:
Good Work follows Jason (Jeff Stern) for six years, across the country and back, as he forgets himself and does nothing to prevent his rise to corporate superstardom, until one day when he decides to try and start over.

He endures breakups, rejections, unsolicited advances, and what might be a genuine shot at love. Depending on who you ask, he is either a tremendous success or a colossal failure. Jason's aiming for a fundamental change in the social order and an intimate connection of some kind... which is more unlikely?

Plot summary:
In 2004 Boston, Jason Hammond (Jeff Stern) spends his time scalping tickets and playing dice games as his relationship with Delle falls apart. He briefly attends business school in Milwaukee before getting hired at a self-described avant-garde strategy think tank, where he immediately earns a reputation for thinking outside the box. Jason harbors vague ambitions of somehow changing the system from the inside, even as he rockets up the corporate ladder. Genuine personal connections continue to elude him.

Four years later, and despite tremendous success, Jason leaves his job, feeling that he is slowly losing himself. He returns to Boston and makes a new life selling vintage clothes online, working on his radical blog, and living with his girlfriend Beth.