[1] My primary concern is whether or not skepticism also includes being skeptical about skepticism itself or if this mode of approaching beliefs about reality and existence is somehow immune to its own nature?

Surely a skeptic about all beliefs should also be skeptical about the belief that "skepticism is the best way to approach the world I encounter- be it in private mental worlds or in the world of supposedly shared, solid things".

[2] Often, it is said that there are generally three types of philosophical methods: Rationalism, Empiricism, and Skepticism.

[2.1] Rationalism supposes that the mind can determine what is true through a process of reasoning and imagining apart from scientific observation.

[2.2] Empiricism, on the other hand, supposes that what is true about reality can best be determined by observing the natural world around us.

[2.3] Skepticism supposes that both of these modes of coming to knowledge are flawed, perhaps fatally so, and that all beliefs about the world should be seen without grounds.

That is, perhaps, in the cases of those beliefs that are not about our immediate environment. I need not, for example, suppose my car still exists outside my apartment but I need believe that the chair I am sitting in will probably support my weight for the moment.

[3] Being skeptical about skepticism yields the negation of skepticism by being a skeptic. Is it then, a contradiction to be a skeptic? Is it like taking hold of a sturdy branch when the branch is, itself, attached to nothing whatsoever?

Does the method of analysis employed in skeptical thinking not undermine itself in this very way? Or, can the skeptical backtrack go on, ad infinitum, where we can be skeptical of our skepticism about skepticism itself and therefore somehow end up back in the mode of doubting?

[4] We can not be absolutely certain of anything other than that there is something going on here or somewhere at the moment we suppose such a thought. Descartes was certainly right about this.

We write, we read, we think, and, therefore, while we are doing something there must be something doing or being or existing. Nothing more than this can be kept from the jaws of the true skeptical maw, which eats all beliefs and shows them to exist in the ungrounded minds of mere simpletons.

[5] But what of this paradox of skepticism about being skeptical? Is there any merit in believing that which can not be proven absolutely but for which there is some form of justification or reason to hold such a belief?

Is my belief that my car still exists in the parkinglot outside the walls of my abode a necessarily true belief? Of course not, because myriad scenarios that are imaginable remove my car from existing outside or even from having ever existed at all, except, perhaps, for in my delusional mind that only conjures up the idea of a car when, in fact, I have never had a car.

[6] Should I have faith that my car exists outside? What difference does it make? Should I stick to only beliefs about my immediate sensory environment? But what good are these beliefs, either, in the light of a skeptical torch that razes all beliefs except that there is something and, perhaps, (and only perhaps) that there is contrast here as well.

For if there were not both something and contrast, then how could there be any difference at all? And, without any difference at all, how could there be words to read? Words require contrast to be seen, do they not?

[7] The skeptical skeptic can go back to either empiricism or rationalism as a place to be for a while, if it is true these are the only two choices. Can we, perhaps, be agnostic about whether we are a skeptic, a rationalist, or an empiricist? Can we put on the hat of any one of these, at will, but never remain as any one in particular? Is lack of commitment not a form of skepticism?

[8] The true skeptic will squirm when asked their view of how skepticism affects being a skeptic because commitment to a belief would seem anathema to the very principle of skepticism.

But, is it not commitment to not commit? Is it faith in the power of doubting that allows the skeptic to forge ahead, clean of the soiled mental representations that are, at base, only assumptions within a skpetical paradigm?

[9] I have more questions than answers here, but all the questions seem to point towards the one idea that doubting as a way of navigating beliefs about reality is subject to doubt itself. The doubter must also doubt the doubting unless they are willing to be certain of skepticism's trumping of other ways of seeing the world.

Perhaps some beliefs are good to have and maybe faith in some things can be beneficial to one's experience of reality. They need not be, but to try all modes of interpreting existence would appear to be in line with a less than absolute skeptic's progression of experience.

[10] Does a skeptic about how a strawberry will taste not ever taste the red fruit because they are skeptical that it will taste good? Or, does the skeptic allow sampling of experiences so as to better understand their realtionship to something like a piece of ripe fruit?

Is a skeptic unable to take vacations from the skepticism in order to make a temporary or experimental leap of faith as the philosopher Søren Kierkegaard suggested was necessary for understanding certain realms of the world?

Well, certainly a strawberry and god can not be said to be anything like each other- at least not unless one is a pantheist, in which case it is true, from the pantheist's perspective, that the strawberry is literally equivalent to god.

[11] What converts a believer into a skeptic and vice-versa? Does the believer begin a process of doubting and the doubter begin a process of believing? Perhaps there are risks and rewards for both. A skeptic can not be let down because they were already skeptical of anything to hold them up. A believer can be let down if the belief never pans out for some reason.

If I am skeptical that I even own a car, then all I can be is very happy when the keys in my drawer open the door to a car outside. But, if I believe I have a car outside and when I go it is gone, then something, like theft, towing, or a hallucination has caused me to be quite disappointed.