This chapter explores the challenges of becoming and being a leader, and how to handle failure. The eight participants spoke of how technology and social media, and effects of the COVID-19 pandemic, have created contemporary leadership challenges. Using their comments as a starting point, as well as my own experience, I explore why technology, social media, and the related work-life changes brought on by the pandemic (including remote work) have added complexity to the leader’s life. I include contemporary research and theory about technology use and how the pandemic exacerbated the effect of technology on leader-follower relationships. I ground these discussions in foundational theories of agency, identity, and even shame.