Corporate learning initiatives frequently lack learner interest and information retention because they are rarely in line with the reality of the modern workplace, and because they are plagued by corporate learning syndromes such as information overload, technostress and attention deficit. This chapter examines how incorporating humor and critical thought into conventional learning methods through workplace satire and aesthetic storytelling might help close these gaps. For practitioners, it offers a practical guide to using satire to critique outdated practices and create relatable learning content. Instead of failing themselves, applying satire enables learners to understand the absurd aspect of failure which inspires them to intervene before these undesirable outcomes.