<p>The nature of work is rapidly evolving, prompting renewed interest in bottom-up approaches to work design that empower employees to proactively shape their roles. In this position paper, we synthesize and extend research on job crafting and playful work design as complementary forms of proactive work behavior and introduce the special issue that brings together cutting-edge contributions on these topics. We review the two dominant models of job crafting, clarify their convergence, and synthesize evidence on the predictors, outcomes, and boundary conditions of crafting across diverse contexts. We further outline the theoretical foundations and empirical benefits of playful work design, highlighting its task-level mechanisms for enhancing energy, engagement, and creativity. Emerging extensions – including career crafting, time-spatial crafting, and AI-enabled proactivity – illustrate the expanding landscape of proactive job and role redesign. We conclude with a research agenda and practical directions for cultivating sustainable proactive work behaviors in contemporary organizations.</p>