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Systems thinking is an integral dynamic throughout varied industries, organizations, and professions. As a process, it impacts learning structures and creates opportunities for knowledge exchange and skill development, encourages engagement, and expands the capacity for reflection (Baumberger-Henry, 2005; Burk, 2020; Finch, 2000; Senge, 2006; Senge et al., 2015). When combined with optimism, systems thinking provides proactive opportunities through agency and motivation to achieve desired goals (Cunliffe, 2008; Luthans & Avolio, 2003; Seligman & Csikszentmihalyi, 2000). The study authors conducted an exploratory study through the lens of systems thinking to examine two disparate organizations, NASA and Disney, and proffer that systems thinking combined with optimism can provide personal and ubiquitous opportunities concomitant with positive organizational outcomes.