The subjective experience of the robber baron

I figured, what is the point of owning a top hat if you only get to trot it out on Halloween? And I'd just come home from a 24-hour work shift, a bit short on sleep, and it was Thanksgiving morning. So I was loading the car for our trip wearing a tall black top hat. 

I'd never really considered what the morphology of a hat said about the people wearing it. This point should have been obvious; the long sloping rear brim of my fire helmet is a case of form following function. In contrast, the top hat's shape renders it unwieldy while performing physical tasks, especially those in confined spaces. Like loading bags into a car, or working in a factory.

Form follows function in the case of the top hat, but I suddenly guessed that its purpose was not utilitarian, but social: to signal that its owner was above the class of men whose fate it was to climb inside the machinery of industry. 

That's no planet-shaking insight, but it's something I probably wouldn't have noticed if I hadn't actually put on the hat and tried to perform light physical labor. You can mock historical re-enactors all you want, but they probably have moments of insight into the subjective lives of those who went before us. That knowledge would be exceptionally difficult to extract from mere scholarship. It's only fully understood when you bang the top of your hat for the third or forth time as you lean into the car door. 

Are there aspects to our subjective consciousness that are simply impossible to comprehend without actually experiencing them for yourself? Do these qualia, if real, suggest that human consciousness cannot be explained purely on the basis of the physical structures that make it possible? I can't really get behind the notion that consciousness is a magical quality that exists independent of physical reality. It's probably more like an emergent property of biological processes taking place in the brain. 

But there is something to the idea that experiences are unique and independent of the mere information used to describe them. Consider the thought experiment posed by philosopher Frank Jackson:

Mary is a brilliant scientist who is, for whatever reason, forced to investigate the world from a black and white room via a black and white television monitor. She specializes in the neurophysiology of vision and acquires, let us suppose, all the physical information there is to obtain about what goes on when we see ripe tomatoes, or the sky, and use terms like ‘red’, ‘blue’, and so on. She discovers, for example, just which wavelength combinations from the sky stimulate the retina, and exactly how this produces via the central nervous system the contraction of the vocal cords and expulsion of air from the lungs that results in the uttering of the sentence ‘The sky is blue’. [...] What will happen when Mary is released from her black and white room or is given a color television monitor? Will she learn anything or not?

Can you really learn anything from the robber baron until you don his hat?