Improving, strengthening, and fine tuning, as well as developing, revitalizing, conserving, and preserving, are all words commonly used in an urban and regional planner’s vocabulary. More nebulous are the concepts of it, thyself, which are the other in planning thinking and professional interventions. Who, what, how, when, and where will it be carried out? If conscious and aware of one’s actions, oneself ought to be able to answer these questions without deference to its outcomes. However, it is commonly recognized that we are unable, and at times unwilling, to understand others’ reaction to a proposal, even when put forward according to established common norms and traditions and socio-economic, environmental, cultural, and legal orders. The purpose of this paper is to review various planning challenges derived from earlier lived and or researched experiences that have already occurred, others taking place here and now, as well as others in need of further conceptualization and study. The review methods build not only upon the now classical sustainability framework, but also upon the more recent and alternative Soft City approach centered on place, movement, and sociability. It is believed that the planning topics and methods analyzed in this review can help reach carbon neutrality goals, promote climate urbanism, accomplish higher utilization of renewable energy, and reduce automobility levels, all goals conducive to graceful bliss and authentic happiness.