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The aftermath of industry-wide mass layoffs has led to an increasingly discontent and disillusioned tech workforce. Our empirical study with 29 laid off tech workers presents critical reflections on tech work and the tech industry in the aftermath of mass layoffs. Through weekly creative reflection activities over 5 weeks as well as focus groups, we find that tech workers experience alienation and unfulfillment with their work. Tech workers expressed conflicted emotions in assessing their attachment to tech work as a site of labor, oscillating between discomfort with the current status of the tech industry and lack of agency in choosing alternatives. We argue that tech workers are embroiled in cruelly optimistic relationships with tech work, and trace the implications of this on conflicting sociotechnical imaginaries shaping tech work, affective attachments in the tech industry, and tech worker resistance and organizing.