The purpose of Air Transportation is to move people and cargo safely, efficiently and swiftly to their destinations. The companies and individuals who use aircraft for this purpose, the airspace users, desire to operate their aircraft according to a dynamically optimized business trajectory for their specific mission and operational business model. In current operations, the dynamic optimization of business trajectories is limited by constraints built into operations in the National Airspace System (NAS) for reasons of safety and operational needs of the air navigation service providers. NASA has been developing and testing means to overcome many of these constraints and permit operations to be conducted closer to the airspace user's changing business trajectory as conditions unfold before and during the flight. A roadmap of logical steps progressing toward increased user autonomy is proposed, beginning with NASA's Traffic Aware Strategic Aircrew Requests (TASAR) concept that enables flight crews to make informed, deconflicted flight-optimization requests to air traffic control. These steps include the use of data communications for route change requests and approvals, integration with time-based arrival flow management processes under development by the Federal Aviation Administration (FAA), increased user authority for defining and modifying downstream, strategic portions of the trajectory, and ultimately application of self-separation. This progression takes advantage of existing FAA NextGen programs and RTCA standards development, and it is designed to minimize the number of hardware upgrades required of airspace users to take advantage of these advanced capabilities to achieve dynamically optimized business trajectories in NAS operations. The roadmap is designed to provide operational benefits to first adopters so that investment decisions do not depend upon a large segment of the user community becoming equipped before benefits can be realized. The issues of equipment certification and operational approval of new procedures are addressed in a way that minimizes their impact on the transition by deferring a change in the assignment of separation responsibility until a large body of operational data is available to support the safety case for this change in the last roadmap step. This paper will relate the roadmap steps to ongoing activities to clarify the economics-based transition to these technologies for operational use.sers of the National Airspace System (NAS) -airlines, general aviation, unmanned vehicles, and military -all have specific objectives for their respective operations that vary widely in purpose, but each benefits from the degree of operational autonomy they are permitted in the performance of their individual missions. In order to provide safety in these flight operations, extensive and restrictive rules and procedures have emerged over many decades that limit or constrain the operations to the degree required by human and other limitations in the systems that have safety responsibility. T...