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Every job has tradeoffs. When choosing an occupation, individuals are faced with choices about pleasure, freedom, security, and financial gain. This case study invites readers to consider how workers manage emotions and work-life spillover by contrasting the experiences of white-collar workers with an example of nontraditional workers—adventure workers, or individuals who have short-term adventurous jobs or perform seasonal work to support an adventurous lifestyle. An understudied group in organizational communication scholarship, nontraditional workers do not fit into the white-collar, ideal worker identities commonly represented in organizational communication research. To examine this understudied group along with a range of different work-related emotions, Amy's story and work-life experiences as a seasonal adventure worker are contrasted with the experiences of her brother and his friend who are employed in what she views as “beige cubicle hell.” These characters grapple with what makes work emotionally fulfilling and the tradeoffs they face in balancing security with freedom.