If someone starts out as a junior designer and keeps practicing, what are some benchmarks to show they have progressed as a better designer?
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If you are asking for within the realms of UX, then UX Design Practice Verticals can be a good measurement for you.
Its a grid, made of eight columns standing for main domains in UX, and six grades of depthness going from practical to strategical areas of practise. It was introduced at UXmatter article The T-Model and Strategies for Hiring IA Practitioners, but explained solely for Information Architects. Nevertheless, it matches Visual Design either.
I like this approach, because it has well thought categories and shows the differences as well as overlaps of each specialist in the field of "Computer Design". And it gives a sort of guidance, where to grow and what to leave aside.