
Skepticism is the royal gateway to philosophy. If we take what we already know for granted, there would be no room for inquiry, curiosity, or intellectual wonder. Skepticism is an act of iconoclasm towards the pillars upon which our current knowledge stands, but what happens if the object of skepticism is the capacity to know itself?
What Exactly IS Skepticism, Anyway?

Skepticism is an attitude, a philosophical stance rather than a doctrine, directed towards certain bodies of knowledge. The attitude is essentially epistemological, investigating whether certain knowledge claims are justifiable or mere beliefs, opinions, and dogmas. There are diverse schools of skepticism that correspond to different classifications of knowledge claims. For instance, if you were a religious skeptic, you would question the legitimacy of religious prepositions. Likewise, if you were a moral skeptic, you would critically question the validity of claims in the field of ethics. As a general rule, every field is susceptible to skepticism, including the field of epistemology itself from which skepticism sprouts.
The Nature of Epistemological Skepticism

In epistemological skepticism, the possibility of knowledge itself is called into question. If you were an epistemological skeptic, you would question if you can know anything for sure in the first place. The very possibility of knowledge claims is no longer taken for granted, presenting us with a paradox. If we issue a verdict against the possibility of knowledge claims, arguing that knowledge is not attainable, then that proposition itself is a knowledge claim. This mirrors the famous Socratic paradox: “All I know is that I know nothing”. Epistemological skepticism, despite its apparent contradiction, is a recognition of our limitations as knowing subjects that critically evaluates the reliability of the different ways we acquire knowledge, particularly the reliability of sense perception and reason.
5 Powerful Ways to Question EVERYTHING You Know

Agrippa was a 1st-century CE Greek philosopher known as Agrippa the Skeptic. Although little is known about him, he is famous for outlining the foundations of epistemological skepticism by demonstrating the different obstacles we encounter when attempting to justify a knowledge claim. Agrippa’s five modes or tropes consist of five different ways that an argument can be undermined.
1. Dissent or Disagreement

Every topic can have equally strong contradicting arguments. For example, many philosophers have skillfully argued for and against the existence of God. There is no knowledge claim that is immune to challenge. Hence, all knowledge remains inconclusive.
2. Infinite Regress
Every justification for a knowledge claim requires another justification, ad infinitum. For example, we can argue that the sky is blue. To justify that claim, we may appeal to the evidence from our sensory perception of the sky, but then we must justify the reliability of our senses, which in turn will require further justifications. Justifying a knowledge claim requires an endless chain of evidence.
3. Relativity

Knowledge is conditioned by the knower, rendering all knowledge relative to the knowing subject. We don’t know anything in a vacuum, but knowledge is necessarily part of a context of which we are a part. While the most obvious example is different aesthetic judgments, philosophical idealism holds that our experience of reality as a whole is inherently subjective.
4. Assumption
All knowledge rests on an unprovable assumption or hypothesis. This goes back to the problem of infinite regress and the need for a starting point in the chain of knowledge justifications. This is a critique of foundationalism, which takes a first principle as the foundation of knowledge. For example, “I think therefore I am” is the foundation of René Descartes’ ideas, i.e. it is the starting point of the chain of justifications for other knowledge claims in Cartesian philosophy. Agrippa argues that foundationalism is built on assumption rather than truth.
5. Circularity

A claim may use justifications that presuppose the acceptance of the initial claim itself, resulting in circularity. For example, one can argue that scriptures are divine revelations. One may then appeal to certain scriptural verses that testify to this claim. However, the justification relies on accepting the initial claim of the divine order of scriptures, without which verses hold no epistemological authority to convince us.
Can You Find Peace in NOT Knowing?

Agrippa adhered to phyrrhonism – the oldest school of philosophical skepticism, founded by Aenesidemus and inspired by Phyrrho of Elis. Phyrrhonism promotes living without making any judgments about the truth or falsehood of knowledge claims. Staying faithful to our incapacity to know anything for sure, we can neither refute nor accept knowledge. According to phyrrhonism, suspending judgments and avoiding belief regarding the truth or falsehood of any preposition is conducive to a state of mental tranquility, known in Greek as ataraxia.