A better analogy would be Taleb's "green lumber" story.[0] The narratives we assign to things don't necessarily correspond to what really moved the needle forward. The ability to get things done might sometimes be influenced by historical reading, but it is mostly a factor of reading the present, creating new knowledge, and spending most of your energy on the problems at hand as they actually stand. A person like Zuck might draw parallels from their reading of the classics (to name one notorious example) but in practice their success will be contingent on making decisions in real time with few helpful analogies, or general principles for which historical reading is not strictly necessary. The journalists then comparing Zuck to Augustus are then probably misattributing the causal relationship.
There will be a historical post-facto rationalization of what went down for anything happening in the recent past, but the meat we draw from historical analogies is often poorly applicable since the divergence between the map and the territory is so large. The difference between reality and a game of chess is indeed paramount here, but for different reasons. The past is so complex that the lessons we draw from it are likely to just be distorted narratives that are already just a reflection of the present.
>To be honest I'm not even sure I can think of a way you can completely ignore history and still be able to do useful work of any kind.
In Levandowski's own example, he learned what existed in his time and then built useful things from there without worrying too much about the details of past beyond the directly visible iceberg spire in the present. This is broadly applicable to many fields and there are many people who did the same. It's tautologically true that disciplines that need to draw on the past to move on will do so, such as biology, but that doesn't say all that much about engineering for instance.
[0]https://fs.blog/2016/11/green-lumber-fallacy/