This paper examines the path that Portland and its region has taken from being a place showing little evidence of "modern city planning practice" to its current and apparently much more attractive state. First, a cautionary note. We have probably been both more and less successful than it sounds. Stories of municipal accomplishment tend to take on greater dimension the further you get from home. Take this one with a grain of salt. From the outside looking in, condition what you see with the following: First, there are no silver bullets or supremely right answers. It takes a mix of many inter-related and complementary actions to be successful. Second, you must make your own successes wherever you find yourself. Use our experience as a reminder that much, truly, is possible. Third, recognize that we are not done yet. Issues of education, social equity, and public safety wait for thorough treatment. Much has been done, but much remains to be attended to.