The obvious subjectivity of Art as an activity begins with one fundamental question (What is Art?) and goes on from there: What is good art? What is an artist? What defines high/low art? Where does the boundary lie between Art and Craft, if ones exists?
For these reasons, it can be difficult to measure artistic progress as such. Somebody who aspires to photorealism in their work can tell whether or not they are getting closer to their goal, but that does not answer the question of whether verisimilitude is, or should be, the aim of representational art.
I tend to go by how closely the final result matches the ideal that was in my head before I began, and whether or not I managed to surprise myself by something turning out better than I expected. The school self-assessments I mentioned before force this kind of reflection, or else I might not have bothered, but I find now that one of the most effective ways to chart a (lack of) progress is by evaluating the mapmaking process.
No map exactly matches the terrain it describes.
Some, of course, are intended to be more abstract than others, but the end result is meant to evoke some sort of recognition, a drawing of parallels between one thing and the other.
If the idea of a piece or the message an artist wishes to communicate is the landscape, the finished piece is the map.
I think in recent years I’ve found my ‘maps’ aligning more closely with the original ideas. I’m not entirely sure whether this is because I’ve become less ambitious, more accomplished, or simply delusional – perhaps the fact that I’m no longer at school being asked, ‘But what does it mean?’ allows me to imagine my work makes more sense than it does.
Whichever of the above is true, I like the idea of art as cartography – all the fun of exploration with less danger of being accused of having led someone the wrong way down the motorway.