This paper offers an examination of thoughtfulness in design, one that focuses more on the mechanism of thought rather than any new methodological spin. The investigation is contextually nested within a temporal discussion of design activity, which is then used to pinpoint the smallest kernel of thought that can initiate a given design effort. Aspects of design articulation and design intent are used to explore the nature, and qualities of thoughtfulness as the design work evolves. An inherent flexibility of perception and consideration attend this thoughtfulness, allowing designers to arrive at new insights, and critically assess their work as efforts unfold. Such flexibility and criticality are seen to be habitually exercised at a minute scale, almost with every drawing or computer stroke. In this way, the endeavor is at times meandering, but always intense, facilitating an organic growth in the design articulation that ultimately results in a sophisticated design response.