Many of the world’s famous events, structures and facilities have been completed with rigorous and scientific project management. No large scale project has ever been successfully delivered without the use of management tools and strategic planning. Project management, therefore, is a very essential field, not only in terms of carrying out world renown events such as the Olympics but in ushering technological developments that countries are so much in need of. The purpose of this paper is to move a notch higher from the classroom theories of project management into a look at an examination of real-world projects where we can dig valuable lessons in project management. How we go about this endeavor necessitates the minds of two management experts, Mr. Jon Smith and Mr. Terry Williams whose decades of expertise make them worthy of our inquiry. Particularly, we look at the projects that the two speakers have provided as an example. These projects are real-world examples and therefore take into accounts variables that theories may have failed to account for. This makes the study more interesting, but down-to-earth. The main body is composed of the following: the background of the projects, the people (client/contractor, supporters, stakeholders) involved in the project, the selection of the project team, the stages within the project life cycle, the definition of the success of the projects, the planning phase, the problems met and how they were overcame, the project management tools and methodologies employed and lastly, the characteristics that made the projects different, exciting and challenging. The analysis also contains comparison and contrast of the two projects, particularly highlighting their strengths and weaknesses. In the end, I will discuss the three important learnings relating to project management. To provide us a background of the products, “Teltrend Inc. designs, manufactures and markets products that interpret and translate translation signals. These products are used by telephone companies to provide voice and data services over the telephone network. The products can be categorized into high capacity products, channelized products, and conversion products” (Business.com, Inc., 2010). Smith worked as a technical director in which the primary roles are to take the technology forward and sort out the project management (Smith, 2010). The project was done in a small company of around 60 people. This particular project is made possible by technology opportunity, especially with the advancement in communication. These projects were primarily carried out for business purposes. The second featured project is the Eurotunnel. The idea of this project can be traced to as early as 1802, when Albert Mathieu, a French mining engineer introduced the first design for the Channel Tunnel (Williams). The Europort is a bridge that spans 500- meters and suspended by means of Kevlar cable, the Euro route is both a drive-through bridge and tunnel system, the channel system is “a last-minute submission consisting of both road and rail tunnels” and finally the Eurotunnel which has a “twin rail channel and a third service channel” (Williams).