In this chapter, we discuss the possibilities and the challenges that come with moving from traditional to digital media investments. In line with popular opinion, we discuss whether digital media offers opportunities that are not available in the more traditional stream. Or whether digital media investments simply seem more attractive due to people’s mentality that the “grass is always greener on the other side.” The way in which companies adapt to digital media is likely to impact company success, it is crucial to understand the rules for these media investments, especially as these investments continue to increase. We begin this chapter by highlighting how digitalization has led to new principles for planning, designing, and evaluating media investments, and how companies must work in new ways to handle this change. We then discuss each area of research and summarise the valuable implications.