We Generation X members (Gen Xers) are a sinking generation, lost in many ways, together on a proverbial Titanic. This new decade of the 2020s has gotten off to quite a rocky start for many of us. Carving our way forward will require grit, a deep understanding of new economic opportunities, and deep reflection on our country’s history and generational economic challenges. Though age-wise, we have another thirty to forty years to go; we stand at the precipice of whether we’ll go silently into obscurity or if we will create something that will lead to generational prominence for our children and grandchildren. We Gen Xers, especially the nomadic ones (those of us sidelined by Corporate America and either doing our own thing or recently laid off) are pretty much in the same boat. We have common obstacles in the creation of the American Dream for ourselves. Understanding the components that made up the financial disaster of 2008, how my small support role at AIG helped keep the U.S. economy afloat, and the generational wealth and leadership opportunities at our doorstep right now are critical to reversing our current misfortunes and restoring generational abundance. This book discusses: inside lessons learned and not yet shared about the AIG bailout, the role that Dodd-Frank played on our current socioeconomic status, some of the career opportunities that will be available to us, and the role that financial and technological advancement could play in our daily lives. This book courageously explores blockchain technology and cryptocurrencies, and how we can leverage them, generationally, for the re-generation of Gen Xers sidelined by Corporate America and Wall Street.