As stated eloquently by the former British Prime Minister Winston Churchill, “We shape our buildings and afterwards our buildings shape us”. To paraphrase Churchill in the context of urban mobility, we shape our transport, and it will shape us; make sure we shape it well, so we will be well-shaped too. To be more specific, we shape our transport system as a living structure, and afterwards it shapes our mobility towards sustainability. The notion of living structure, conceived and developed by Christopher Alexander in the magnum opus The Nature of Order, is also called wholeness or life or beauty, which is defined mathematically as a recursive structure, and exists in space and matter physically, and is reflected in our minds and hearts psychologically. There are two fundamental laws governing the living structure: scaling law and Tobler’s law. Scaling law is available across all scales ranging from the smallest to the largest, and it states that there are far more smalls than larges in a living structure. Tobler’s law, also known as the first law of geography, is available at one scale, and it states that nearby things tend to be more or less similar or related. In this presentation, I will add a geospatial perspective on sustainable urban mobility in the era of big data. Distinct from the existing geospatial perspective, which is a bit too geometric, focusing on geometric details such as locations, sizes and directions (or geometric primitives of points, lines, polygons or pixels), and a bit too mechanistic, as shown in raster and vector formats, I have been advocating a topological perspective that enables us to see the scaling or fractal or living structure using the emerging geospatial big data. I will use two concepts natural cities and natural streets to demonstrate living structures of Greece at both country and city levels, and further argue for the kind of topological and scaling analysis in order to better understand our transport system as the living structure. Human mobility is substantially shaped by the living structure, so to achieve sustainable urban mobility is, to a great extent, to make the underlying transport system more whole or more living or more beautiful.