The telecommunications sector is one of the most innovative, high-growth, capitalintensive yet volatile sector of the economy. This research addresses critical concerns of how, when, and why an enterprise or a service provider should undertake new investments. The study investigates the power of flexibility in investment decision making process, by applying the real options methodology. Five case applications are studied: a) investment decisions in next generation wireless networks; b) investing in integrated wireless networks; c) migration to wireless broadband internet services; d) valuing deployment of Wi-Fi networks in enterprise markets; and e) valuing Hosted VOIP services for enterprise markets. The case studies are analyzed both qualitatively and quantitatively.