This chapter examines digitalization initiatives from a project perspective. It describes ten success factors and ten pitfalls that should be considered or avoided in digitalization projects within companies. These factors serve as a guide for companies to effectively implement digitalization projects and leverage the benefits of digitalization. The importance and relevance of these factors may vary depending on the situation and industry. The listed obstacles can jeopardize the success of digitalization projects, but they can be avoided through well-planned approaches. Companies should strive for a holistic approach, identify potential sources of error early, and take appropriate measures to successfully shape the projects. Careful planning, clear communication, appropriate resource allocation, and a good change management strategy can help reduce shortcomings and maximize the success of digitalization projects.