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In the fall of 2011 twenty-three year old Caitlyn Gregory is a promising Junior Placement Strategist with a leading career placement firm in lower Manhattan. When she’s given the opportunity to present data for an impressive potential client Caitlyn is confident her work will seal the lucrative deal, and earn her a promotion.

At the same time her long distance relationship is suffering. Caitlyn’s boyfriend wants more security about their future together but she’d rather focus on getting better at her job than discussing cohabitation, much less marriage. Her desire to stay in New York and pursue corporate goals eventually prompts David to break up with her. The next day Caitlyn is further blindsided when she’s fired hours before the client meeting.

Newly single and unemployed, Caitlyn is incensed by the sudden changes in her life and takes counsel from her neighbor, a radical and zany art student named Paula. When Paula introduces her to Michael, the charming but slightly disturbed creative entrepreneur, Caitlyn is intrigued by his uninhibited lifestyle and inspired by his casual sense of entitlement and indulgence.

As she battles the desperation of being jobless Caitlyn detaches herself from the concerns and opinions of those closest to her. She aggressively refuses her family’s suggestion to leave New York and return home. Caitlyn is determined to remain independent. Something has to give, and she doesn’t expect it will be her.