Dewey was born in Burlington, Vermont of modest family origins. He received his PhD from the Krieger School of Arts & Sciences at Johns Hopkins University in 1884. From 1904, he was professor of philosophy at Columbia University. Dewey's most significant writings were "The Reflex Arc Concept in Psychology" (1896), a critique of a standard psychological concept and the basis of all his further work; Human Nature and Conduct (1922), a study of the role of habit in human behavior; The Public and its Problems (1927), a defense of democracy written in response to Walter Lippmann's The Phantom Public; Experience and Nature (1929), Dewey's most "metaphysical" statement; Art as Experience (1934), Dewey's major work on aesthetics; A Common Faith (1934), a humanistic study of religion; Logic: The Theory of Inquiry (1938), an examination of Dewey's unusual conception of logic; and Freedom and Culture (1939), a political work examining the roots of fascism. While each of these works focuses upon one particular philosophical theme, Dewey wove in all of his major themes into everything he wrote.

Educational philosophy
As can be seen in his Democracy and Education Dewey attempts to at once synthesize, criticize, and expand upon the democratic or proto-democratic educational philosophies of Rousseau and Plato. He saw Rousseau's as overemphasizing the individual and Plato's as overemphasizing the society in which the individual lived. For Dewey, this distinction was by and large a false one; like Vygotsky, he viewed the mind and its formation as communal process. Thus the individual is only a meaningful concept when regarded as an inextricable part of his society, and the society has no meaning apart from its realization in the lives of its individual members. However, as evidenced in his later Experience and Nature Dewey recognizes the importance of the subjective experience of individual people in introducing revolutionary new ideas.

For Dewey, it was vitally important that education not be the teaching of mere dead fact, but that the skills and knowledge which students learned be integrated fully into their lives as persons, citizens and human beings. At the Laboratory School which Dewey and his wife Alice ran at the University of Chicago, children learned much of their early chemistry, physics, and biology by investigating the natural processes which went into cooking breakfast—an activity they did in their classes. This practical element—learning by doing—sprang from his subscription to the philosophical school of Pragmatism. The school failed within three years and forced Dewey to leave Chicago. He then created his famous Lincoln School in Manhattan that also failed in a short amount of time.

His ideas, while quite popular, were never broadly and deeply integrated into the practices of American public schools, though some of his values and terms were widespread. Progressive education (both as espoused by Dewey, and in the more popular and inept forms of which Dewey was critical) was essentially scrapped during the Cold War, when the dominant concern in education was creating and sustaining a scientific and technological elite for military purposes. In the post-Cold War period, however, progressive education has reemerged in many school reform and education theory circles as a thriving field of inquiry.

Dewey and historical progressive education
The most basic idea of John Dewey's with regard to education was that greater emphasis should be placed on the broadening of intellect and development of problem solving and critical thinking skills, rather than simply on the memorization of lessons. While Dewey's educational theories have enjoyed a broad popularity during his lifetime and after, they have a troubled history of implementation. Dewey's writings can be difficult to read, and his tendency to reuse commonplace words and phrases to express extremely complex reinterpretations of them makes him unusually susceptible to misunderstanding.

So while he remains one of the great American public intellectuals, his public often did not quite follow his line of thought, even when it thought it did. Many enthusiastically embraced what they thought was Deweyan teaching, but which in fact bore little or somewhat perverse resemblance to it. Dewey tried, on occasion, to correct such misguided enthusiasm, but with little success. Simultaneously, other progressive educational theories, often influenced by Dewey but not directly derived from him, were also becoming popular, and progressive education grew to comprehend many, many contradictory theories and practices, as documented by historians like Herbert Kliebard.

It is often thought that progressive education "failed", though whether this view is justified depends on one's definitions of "progressive" and "failure". Several versions of progressive education succeeded in transforming the educational landscape: the utter ubiquity of guidance counseling, to name but one example, springs from the progressive period. However, radical variations of educational progressivism were hardly ever tried, and often were troubled and short-lived.

Deweyan pragmatism
Dewey is one of the three central figures in American pragmatism, along with Charles Sanders Peirce, who coined the term, and William James, who popularized it—though Dewey did not identify himself as a pragmatist per se, and instead referred to his philosophy as "instrumentalism". Dewey worked from strongly Hegelian and Neo-Hegelian influences, unlike James, whose lineage was primarily British, drawing particularly on empiricist and utilitarian thought. Dewey was also not nearly so pluralist or relativist as James. He held that value was a function not of whim nor purely of social construction, but a quality situated in events ("nature itself is wistful and pathetic, turbulent and passionate" (Experience and Nature)).

He also held, unlike James, that experimentation (social, cultural, technological, philosophical) could be used as a relatively hard-and-fast arbiter of truth. For example, James felt that for many people who lacked "over-belief" in religious concepts, human life was shallow and rather uninteresting, and that while no one religious belief could be demonstrated as the correct one, we are all responsible for taking the leap of faith and making a gamble on one or another theism, atheism, monism, or whatever. Dewey, in contrast, while honoring the important role that religious institutions and practices played in human life, rejected belief in any static ideal, such as a theistic God. For Dewey, God was the method of intelligence in human life: that is to say, rigorous inquiry, or, very broadly conceived, science.

As with the reemergence of progressive philosophy of education, Dewey's contributions to philosophy as such (he was, after all, much more a professional philosopher than a thinker on education) have also reemerged with the reassessment of pragmatism, beginning in the late 1970s, by thinkers like Richard Rorty, Richard Bernstein and Hans Joas.

Because of his process-oriented and sociologically conscious view of the world and knowledge, he is sometimes seen as a useful alternative to both modern and postmodern ways of thinking. Dewey's non-foundational approach pre-dates postmodernism by more than half a century. Recent exponents (like Rorty) have not always remained faithful to Dewey's original vision, though this itself is completely in keeping both with Dewey's own usage of other thinkers and with his own philosophy— for Dewey, past doctrines always require reconstruction in order to remain useful for the present time.

Epistemology of transaction
Dewey's philosophy has gone by many names other than "pragmatism". He has been called an instrumentalist, and experimentalist, an empiricist, a functionalist, and a naturalist. The term "transactional" may better describe his views, a term emphasized by Dewey in his later years to describe his theories of knowledge and experience.

The terminology problem in the fields of epistomology and logic is partially due, according to Dewey and Bentley, to, inefficient, and imprecise use of words, and concepts that reflect three historic levels of organization and presentation. In the order of chronological appearance, these are :

- Self-Action: Prescientific concepts regarded humans, animals, and things as possessing powers of their own which initiated or caused their actions.
- Interaction: as described by Newton, where things, living and inorganic, are balanced against thing in a system of interaction, for example, the third law of motion that action and reaction are equal and opposite.
- Transaction: where modern systems of descriptions and naming are employed to deal with multiple aspects and phases of action without any attribution to ultimate, final, or independent entities, essences, or realities.

A series of characterizations of Transactions indicate the wide range of considerations involved.

- Transaction is inquiry in which existing descriptions of events are accepted only as tentative and preliminary. New descriptions of the aspects and phases of events based on inquiry may be made at any time.
- Transaction is inquiry characterized by primary observation that may range across all subjectmatters that present themselves, and may proceed with freedom to re-determine and re-name the objects comprised in the system.
- Transaction is Fact such that no one of the constituents can be adequately specified as apart from the specification of all the other constituents of the full subject matter.
- Transaction develops and widens the phases of knowledge, and broadens the system within the limits of observation and report.
- Transaction regards the extension in time to be comparable to the extension in space, so that “thing” is in action, and “action” is observable in things.
- Transaction assumes no pre-knowledge of either organism or environment alone as adequate, but requires their primary acceptance in a common system.
- Transaction is the procedure which observes men talking and writing, using language and other representational activities to present their perceptions and manipulations. This permits a full treatment, descriptive and functional, of the whole process inclusive of all its contents, and with the newer techiques of inquiry required.
- Transactional Observation insists on the right to freely proceed to investigate any subjectmatter in whatever way seems appropriate, under reasonable hypothesis.

Illustration of differences between self-action, interaction, and transaction, as well as the different facets of transactional inquiry are provided by statements of positions that Dewey and Bentley definitely did not hold and which never should be read into their work.

1. They do not use any basic differentiation of subject vs. object; of soul vs body; of mind vs matter; or self vs nonself.
2. They do not support the introduction of any ultimate knower from a different or superior realm to account for what is known.
3. Similarly, they do not tolerate "entities" or "realities" of any kind intruding as if from behind or beyond the knowing-known events, with power to interfere.
4. They exclude the introduction of "faculties" or other "operators" of an organism’s behaviors, and require for all investigations the direct observation and contemporaneous report of findings and results.
5. Especially, they recognize no names that are offered as expressions of “inner” thoughts, nor of names that reflect compulsions by outer objects.
6. They reject imaginary words and terms said to lie between the organism and its environmental objects, and require the direct location and source for all observations relevant to the investigation.
7. They tolerate no meanings offered as "ultimate" truth or "absolute" knowledge.
8. Since they are concerned with what is inquired into, and the process of knowings, they have no interest in any underpinning. Any statement that is or can be made about a knower, self, mind, or subject, or about a known thing, an object, or a cosmos must be made on the basis of, and in the language applicable to the specific investigation.

In summary, all of human knowledge consists of actions and products of acts in which men and women participate with other human beings, with animals and plants, as well as objects of all types, in any environment. Men and women have, are, and will present their acts of knowing and known in language. Generic man, and specific men and women are known to be vulnerable to error. Consequently, all knowledge (knowing and known) whether commonsensical or scientific; past, present, or future; is subject to further inquiry, examination, review, and revision.