This article investigates the relationship of learning and its infrastructure using Web 2.0 technologies to facilitate the acquisition of skills needed to succeed in a global economy. We explore the learning phenomenon as a way to bring forward a process of continuous improvement supported by social software. We use a commonly accepted definition of learning to evaluate different learning theories, since it seems that the definition of learning itself is not a major source of difference between learning theories. Their differences are over issues of interpretation, not over definition. The theories reviewed are used in the design of a framework to assess the infrastructure against expectations of skill proficiency using Web 2.0 tools, i.e., wikis, blogs, social bookmarking, tagging, etc. which must emerge as a result of registering in an introduction to business information and communication technologies (ICT) course in a Canadian university. In this course, we use Friedman’s (The world is flat: a brief history of the twenty-first century release 3.0, Picador, New York, 2007) thesis that the “world is flat” to discuss issues of globalization and the role of ICT. Students registered in the course are usually familiar with some of the tools we introduce and use in the course. The students are members of Facebook or MySpace, regularly check YouTube, and use Wikipedia in their studies. These tools are the tools to socialize. In our course, we broaden the students’ horizons and explore the potential business benefits of such tools and empower the students to use Web 2.0 technologies within a business context.