We present three studies that investigate the effectiveness of multiple glanceable part-to-whole proportion representations on smartwatch faces. Our goal was to understand how quickly and accurately people can make judgments about their progress toward multiple goals displayed in a small space. We designed our three studies with increasing external validity. The first study compared bar charts, radial bar charts, and text representations-shown with a digital time display. The second study added an analog time dial as a distractor to increase the complexity of the watch face. To emulate realistic viewing conditions, the third study investigated the effect of viewing angles. In Study 1 bar and radial bar charts outperformed text representations, in Study 2 adding an analog time dial as a distractor did not affect task performance, and in Study 3 only the most extreme angle led to some performance decrease. Supplementary material is available at https://osf.io/ad2z7/.