Technical Debt, considered by many to be the 'silent killer' of software projects, has undeniably become part of the everyday vocabulary of software engineers. We know it compromises the internal quality of a system, either deliberately or inadvertently. We understand Technical Debt is not all derogatory, often serving the purpose of expediency. But, it is associated with a clear risk, especially for large and complex systems with extended service life: if we do not properly manage Technical Debt, it threatens to "bankrupt" those systems. Software engineers and organizations that develop software-intensive systems are facing an increasingly more dire future state of those systems if they do not start incorporating Technical Debt management into their day to day practice. But how? What have the wins and losses of the past decade of research and practice in managing Technical Debt taught us and where should we focus next? In this paper, we examine the state of the art in both industry and research communities in managing Technical Debt; we subsequently distill the gaps in industrial practice and the research shortcomings, and synthesize them to define and articulate a vision for what Technical Debt management looks like five years hence.