The blurring of boundaries between work life and private life, between Spredsheets and Facebook, between societal and private means that we need to reconsider learning both in the perspective of adoption of technological change and, as diffusion of continuous innovation. Both organizations and technologies are undergoing fundamental changes that transform and create new challenges in the ways we work and learn. Many organizations today require continuous development and effective learning processes to meet the challenges of globalization and digitalization. The questions that need to be raised are what new skills need to be recruited, and how can the capabilities and functionality be distributed among a mixture of both human and technical "workforce"? In this position paper we discuss arguments for a future research agenda where new digital phenomena's are viewed from a"learning at the digital boundaries" perspective, taking into account different waves of digitalization and infrastructural challenges at the boundaries of organizational setting and private life.