Reduced automobile dependence and improved competitiveness of transit for a wider variety of trip purposes are common goals of most attempts to improve the sustainability of urban transportation in medium and large Canadian cities. However, our collective ability to ‘get things done’ and make meaningful and cost effective improvements in public transit appears to be on the decline, largely due to conflicting objectives, a multiplicity of government agencies, questionable models of transportation agency governance, the lack of realistic financial models, and a very cumbersome process for the review of transportation decisions. This paper focuses on three important aspects urban transportation decision making, namely, governance models, the planning process, and more innovative financing. First and foremost, it highlights the crucial role that good governance plays in the delivery of effective solutions required for the economic well being and liveability of our cities, and suggests new models of governance. Second, the paper also focuses on the planning process itself, emphasizing the need for a return to traditional bottom-up planning based on assessments of real needs and benefits, as a substitute for top-down, politically motivated planning that characterizes most transportation initiatives today. Finally, the paper treats the matter of finance. Funding programs that must stand the test of the annual municipal, provincial, and federal budget processes are simply inadequate to provide the predictability needed for effective long-term infrastructure planning. Funding should involve more than simply pleading for more project-specific dollars from the provincial and federal governments. Because experience shows that short-term, project-specific infrastructure programs lack continuity, create uncertainty, and alter local priorities, the paper identifies a number of measures for placing transit finance on a more predictable basis, including a shift to funding guarantees that can be used to service debt and leverage financial community participation in accelerated infrastructure expansion.