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Emotional Literacy is increasingly recognized as an important component of holistic education and personal development, with a growing body of evidence supporting its positive impact on human well-being and social functioning. This writing explores the ways emotional literacy informs the construction and absorption of messaging, and illustrates how the demystification of our inner worlds opens up the possibility for greater connection: to the present, to others and to ourselves. Designers, often credited as orchestrators of our social environment, have the responsibility to stay present and creative in the face of socioeconomic and environmental peril. I argue that this presents a case for emotional literacy development as a necessary tool in a designer’s kit. This body of work is an exploration of emotional literacy and rhetorical strategy, how their interplay can drive a design process, and the quality of messaging that this can produce. With the goal of mitigating the growing crisis of isolation, how can emotional attunement impact the process of delivering and receiving messages, and shape the development and quality of rhetorical strategies that energize and include (rather than ostracize and alienate) the audience? This research uncovers the methodological approaches of communicators who arguably speak to and from the heart, reveals that revolutionary optimism is the antithesis of dissociation, and documents experimental approaches to designing from an emotionally literate place, and for the promotion and development of this gift.