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Millennials now represent the majority generation and the majority workforce in the U.S. Unlike older generations, millennials claim to desire a more seamless overlap between work and personal lives. This study acknowledges a change in context from work-family balance to work-life overlap, provides evidence that the established relationship between core self-evaluation and job satisfaction holds for millennial workers, and contributes two new constructs and scales to measure technology enabled work-to-life and life-to-work overlap for millennial workers. Results show that technology enabled work-to-life overlap is positively related to job satisfaction and strengthens the CSE-job satisfaction relationship.