On shaping

This week, I'm sharing an essay I wrote for my grad school summer course on education and pedagogy. It explores the concept of "first shape yourself, then society," contrasting the philosophical ideals of self-development advocated by Plato and Eva Brann with the rapid, intervention-first ethos of modern life epitomized by the tech industry.

Books and works referenced:

• Liberal Education - Eva Brann
• The Republic, Book VII - Plato
• A Place of Learning - Michael Oakeshott
• The End of Education, Chapter 1 - Neil Postman

Some human works are best learned by doing. Improving worldly conditions is not among these. A time of receptive learning should precede active intervention; first shape yourself, then society; in particular form views about what makes for human contentment, then interfere judiciously.

Eva Brann makes this striking claim in her description of a liberal education. The idea of prioritizing self-shaping before societal engagement isn't new. In fact, it echoes Plato's conception of an ideal education in The Republic, articulated some two thousand years earlier. He envisioned the brightest minds engaging in a rigorous, multi-decade program—a far cry from our accelerated modern timelines—before they could be considered for public life and the possibility of shaping society.

On one hand, Brann’s assertion feels intuitively wise — to have a positive impact on society, one must first focus on inner refinement and self-development. Cultivating intellectual and, more importantly, moral stances, seem like important prerequisites for effective societal change. Yet, it is discordant with my experience of how the technology startup ecosystem—one of the prominent shapers of society today—operates.

While Brann's focus is on the individual, an ecosystem is made up of individuals, and its character inevitably reflects their shaping. The societal shaping Brann appears to be addressing is more akin to social activism, but her principle applies equally to the kind of entrepreneurship Silicon Valley, the beating heart of the technology ecosystem, espouses. It prides itself in attempting to solve societal challenges and improving worldly conditions.

I have directly participated in, witnessed, and studied various attempts to shape society through technological solutions at small and large scales. This experience reveals a stark contrast between Brann's ideal and the tech world's reality. Learning by doing, which Brann claims is not effective for improving worldly conditions, is the favored method for achieving grand ambitions in Silicon Valley. For the first decade of its existence, Facebook's internal motto was to move fast and break things, signifying the value placed on speed of execution at the expense of judiciousness.

At tech companies, intervention often precedes learning—the reverse of Brann's ideal. The startup process typically involves testing falsifiable hypotheses about how to solve a particular problem, then learning through rapid experimentation. It's a build, measure, learn cycle, in that order. This learning is oriented towards discovering methods for rapid growth and financial success—the criteria that ultimately shape how the tech ecosystem influences society. This approach is the opposite of the kind of receptive learning and judicious interfering Brann envisioned.

The incentive systems of likes and followers underpinning major social networks suggest their leaders have either invested little time contemplating human contentment or have limited their views to superficial, short-term pleasures and instant gratification. I'm not above this criticism. In my own, far less successful venture, I designed social network-inspired educational experiences for high school students. In retrospect, I realize I had neglected to delve deeply into the fundamental questions of the human condition—an exploration that would have been invaluable.

The tech ecosystem's anti-Brann approach has resulted in unprecedented innovation directly impacting worldly conditions, giving us access to boundless information at our fingertips while enabling us to connect with people anywhere in the world. This suggests that, at least in a narrow sense, worldly conditions can be improved in the process of learning by doing. Yet, despite these significant material advances, I sense that something is left to be desired. We find ourselves in a state of collective unease — unmoored from the past, unclear about our future direction, unsure of ourselves.

To summarize, the reality of the technology ecosystem is at significant odds with what I’ll refer to as the Brann Sequence: "first shape yourself, then society." Yet, the unintended consequences and dubious outcomes of technological change suggest a critical lack of meaningful self-development before societal intervention. This tension raises crucial questions about the nature and value of self-shaping in our modern context.

To delve deeper into this topic, this essay explores three key questions: What does shaping oneself entail? In what ways is the Brann Sequence desirable? And what challenges and opportunities emerge when considering the practical implementation of the Brann Sequence?

Shaping oneself

To fully grasp the implications of the Brann Sequence, let's first explore its philosophical roots—Plato's foundational ideas on "the effect of education and the lack of it on our nature" (514a) in Book VII of The Republic.

It's important to note that much of the self-shaping described in The Republic is not self-motivated—that is, it's not driven by individual choice. In fact, Plato's primary concern is the city as a whole, often prioritizing it over any particular citizen or group. He contends that "the law is not concerned with making any one class in the city do outstandingly well," but rather aims to “[harmonize] the citizens together through persuasion or compulsion," ensuring all citizens contribute to the common good (519e).

For Plato, the cultivation of self is about reorienting one’s whole being, turning away from the illusory world of appearances toward what is “truly real.” It is a complete turning around “from what-comes-to-be together with the whole soul, until it is able to bear to look at what is and at the brightest thing that is—the one we call the good” (518c).

Plato uses the cave myth to illustrate the journey of self-shaping and transformation. In this myth, prisoners chained in a cave mistake shadows on a wall for reality. When one prisoner is freed and forced out of the cave, he painfully adjusts to the world of light, eventually recognizing the sun as "the cause of all the things that he and his fellows used to see" (516c).

This myth represents our journey from ignorance to understanding: the cave and chains symbolize our limited perspectives and constraints, the shadows our unexamined beliefs, and the painful ascent our transformative learning process. Seeing the sun represents the pinnacle of understanding—seeing “the form of the good”, grasping the nature of reality, and comprehending the underlying principles of truth and beauty (517b-c).

Plato sees self-development as a gradual process that happens in stages, with each stage building on the previous one. At every step, one gains new insights about reality and consequently, about themselves and their former limitations.

At first, he would see shadows most easily, then images of men and other things in water, then the things themselves. From these, it would be easier for him to go on to look at the things in the sky and the sky itself at night, gazing at the light of the stars and the moon, than during the day, gazing at the sun and the light of the sun. (516a)

This gradual process is painful, highlighting the inherently uncomfortable nature of learning and development.

And if he were compelled to look at the light itself, wouldn’t his eyes be pained and wouldn’t he turn around and flee toward the things he is able to see, and believe that they are really clearer than the ones he is being shown? (515e)

Intriguingly, Plato doesn't specify what causes the prisoner's liberation. He merely states that "one was freed and suddenly compelled to stand up" (515c). This suggests the prisoner's release wasn't voluntary but prompted by some external force. What might this force be? Plato offers a clue at the conclusion of the cave myth:

It is our task as founders, then, to compel the best natures to learn what was said before to be the most important thing: namely, to see the good; to ascend that ascent. (519c)

This reveals further mysteries which are left largely unresolved: What caused the founders to “ascend that ascent” and to “see the good” in the first place? Who, or what, freed them from their chains? Unlike the cave prisoners who “have been there since childhood, with their necks and legs fettered” (514a), were they born unchained? Is it possible to be born without metaphorical chains?

While Plato doesn't explicitly answer these questions or pinpoint a single cause, the text offers clues suggesting a complex interplay of nature and nurture. It implies the importance of innate potential alongside external factors. Rather than getting caught in the circular problem of who educates the educators?, we can acknowledge that compelling the "best natures" to embark on a transformational ascent requires two elements: those possessing such natures, and those capable of guiding them based on prior experience.

This is where Plato's ambitious educational project comes into full view. It doesn't culminate with an individual “seeing the good” at the end of a challenging journey. Such an outcome would be incomplete and unacceptable. Those who have glimpsed the truly real bear a responsibility to engage in civic life and share their hard-won wisdom with others. The ultimate goal is nothing less than the shaping of a just society.

Plato’s educational project is a lifelong one, focused on a select few who are to be the guardians of the city. Starting from childhood, in addition to physical and musical training, potential guardians are expected to engage in mathematical studies because it is “useful in the search for the beautiful and the good!" (531c). He recommends using play rather than compulsion because “…a free person should learn nothing slavishly. For while compulsory physical labors do no harm to the body, no compulsory instruction remains in the soul” (536e).

At age twenty, select individuals are expected to synthesize their early learning, focusing on the interconnectedness of subjects. “Moreover, the subjects they learned in no particular order in their education as children, they must now bring together into a unified vision of their kinship with one another and with the nature of what is” (537c).

At age thirty, those who excel in both intellectual and practical pursuits—including warfare—undergo five years of training in dialectic. Dialectic, a form of philosophical inquiry that collaboratively pursues truth through reasoned argumentation, is held in the highest regard. Plato describes it as "just like a capstone we have placed on top of the subjects, and that no other subject can rightly be placed above it" (534e).

After their dialectical training, these individuals return to public life for 15 years. They assume leadership roles to gain practical experience and demonstrate their steadfastness in applying their knowledge. Only then, at age 50, do those who have successfully passed through all these stages devote themselves to philosophical contemplation while taking turns governing the city as exalted philosopher-kings. Drawing on their deep understanding of the "form of the good," they shape the city and its citizens justly.

Plato's ambitious vision of self-shaping, spanning decades and intricately tied to societal roles, stands in sharp contrast to contemporary approaches. How does Brann's more recent vision of self-shaping through liberal education compare to the first thirty-five years of Plato's educational program?

Given the modern context of large nations rather than small city-states, and the contemporary setting of Brann's ideas, her more limited scope is understandable. She focuses on individual students pursuing undergraduate degrees, confining formal self-shaping to four short years.

The similarities between Brannian and Platonic ideals are undeniable. Brann envisions liberal education as a "stocking of the human soul's treasury with desirable goods." While she doesn't explicitly define these goods, the prominence of Great Books in her educational ideal suggests they are timeless wisdom and fundamental truths. These treasures are to be unearthed through specific modes of engagement with these seminal works.

These modes of engagement are characterized by a delicate balance of radical reverence within the pedagogical framework of small-group seminars. Students should approach the books with profound respect, yet maintain a readiness to challenge established ideas by posing “penetrating questions.” Striking this balance is crucial—excessive reverence or radicality could impede the enrichment of one's soul treasury. While Brann's seminar shares elements of dialogue and inquiry with Plato's dialectic, her guidelines are comparatively flexible. She outlines just three core principles: civility, a willingness to articulate one's thoughts, and respectfully listening to others.

The seminar's primary focus, according to Brann, should be understanding the book's meaning and addressing the “bald question” - Is it true? This, I believe, is where self-shaping truly occurs in Brann's conception of liberal education. When approached correctly, this question prompts self-reflection and uncovers one's implicit worldviews. To illustrate this process of progressive questioning more clearly, it might unfold like this: What do I (and others) think of this book? Do I understand the ideas presented? Do I (and others) agree or disagree with these ideas? What do my responses reveal about myself?

Unlike Plato, Brann's project doesn't solely focus on progressing from shadow-like ignorance to total knowledge. While experiencing the "perennial heights" of truth remains the goal, Brann acknowledges that these truths may already exist within conventional wisdom:

Questions may indeed sometimes dissipate prejudices, but they are as likely to clarify and so to confirm a heritage. A real radical is one who goes to the roots, digs them up, often for more secure reburial, having examined them in the light of reason rather than the murk of rationalization.

A more significant difference lies in the “be-all and end-all” of education and self-shaping. For Plato, as previously outlines, this aim is the creation and maintenance of a just society. For Brann, however, the object is happiness. While acknowledging that "true happiness requires the heightening delimitation of occasional agony, confusion, and even despair," thus recognizing the inherent struggles in learning, she asserts that "liberal schooling must be a present experience of fulfillment, and the acquisition of the unwearying habit of thoughtful happiness."

Brann seems to harbor a strong aversion to reducing education to mere utility, a point we'll revisit later. For now, we can conclude that while Plato's project of self-shaping culminates in a just society, Brann's vision results in an individual cultivated in the habit of thoughtful contentment.

The desirability of the Brann Sequence

Despite their differing ultimate aims, both Plato and Brann emphasize self-shaping before societal engagement. This raises a crucial question: Why might it be preferable to shape oneself before attempting to improve society?

In our rapidly changing, technologically shaped world, understanding the value of self-shaping is increasingly vital. The tech industry's blitzscaling mentality stands in direct opposition to the deliberate, reflective approach championed by Brann and foreshadowed by Plato. To examine the desirability of the Brann Sequence—”first shape yourself, then society”—I’ll consider its potential benefits, its capacity to provide a cohesive narrative, and the hurdles it faces in our modern context.

One argument for shaping oneself before engaging in societal intervention lies in the impact it can have on one’s understanding and subsequent actions. Plato argues that only those who have “seen the good” are truly equipped to guide society. He believes that proper self-shaping enables individuals to see beyond appearances, grasping the underlying principles and causes of societal issues.

…you will see infinitely better than the people there and know precisely what each image is, and also what it is an image of, because you have seen the truth about fine, just, and good things. (520c)

Brann echoes this sentiment in a contemporary context. Her assertion that “A time of receptive learning should precede active intervention” underscores the importance of developing a robust foundation before attempting to shape society. For Brann, this foundation is built through deep engagement with great works and ideas, generating the ability to form nuanced “views about what makes for human contentment.”

Michael Oakeshott's view of liberal learning as an exploration of "the invitation of the culture of antiquity" further bolsters the case for self-shaping. By immersing oneself in the breadth of human thought, individuals "extend the range and the depth of their understanding of themselves." This enhanced self-knowledge and broader perspective are expected to foster a more thoughtful approach to societal shaping.

This enduring perspective, shared by thinkers spanning millennia, lends considerable credence to the desirability of the Brann Sequence.

The sequence also offers an unexpected benefit: a unifying narrative. As Neil Postman argues, "Without a narrative, life has no meaning. Without meaning, learning has no purpose. Without a purpose, schools are houses of detention, not attention."

The Brann Sequence elevates education beyond a mere accumulation of facts and "acquisition of technical know-how." It transforms learning into a profound journey of personal growth and societal engagement, forging a virtuous relationship in which what one learns and how one acts in society are deeply connected. In doing so, it provides an inspiring alternative to the dominant learn skills, make money ethos of today.

While the benefits of self-shaping are evident, the risks of premature societal engagement are equally significant. Plato's cave myth illustrates this danger. The chained prisoners, perceiving only shadows, represent those who engage with society without proper self-shaping. They mistake appearances for reality, leading to misguided actions and beliefs. More alarmingly, they might even attempt to kill the freed prisoner who tries to liberate them, thus severing their only connection to reality.

In the modern context, we can observe parallels in the unintended consequences of hastily deployed technologies. Social media addiction, the spread of misinformation, and privacy breaches are just a few examples of issues that arguably stem from an insufficient understanding of human nature and societal dynamics.

These problems point to Brann's assertion that “Improving worldly conditions is not among these [works best learned by doing].” The complex, interconnected nature of societal issues demands a level of understanding and wisdom that comes from rigorous self-shaping, not just technical expertise. Without this deeper understanding, attempts to shape society often lead to superficial solutions that fail to address root causes or, worse, create new problems.

Despite the desirability of the Brann Sequence and the lack of desirability of its inverse, it’s worth exploring its potential shortcomings.

First, our economy's emphasis on technical skills clashes with the ideal of broader self-development. Brann recognizes this tension, stating, "The necessary acquisition of technical know-how should follow the stocking of the human soul's treasury with desirable goods." However, in a world where practical skills often directly translate into economic opportunities—opportunities on which people's lives depend—advocating for prolonged self-shaping before acquiring these skills may seem out of touch with practical realities. For the ideal of extended self-shaping to be truly effective, it requires a society that values and appreciates it.

Second, there's a risk of becoming trapped in an endless cycle of self-shaping. Plato explicitly addresses this concern. He insists that the finest minds must be compelled to "see the good" and then return to guide others and "share their labors and honors," rather than remaining in isolated contemplation (519c-d). However, without a concrete way to determine when one is sufficiently shaped, there's a danger of using the need for further development as an excuse to avoid real-world engagement.

These challenges don't invalidate the Brann Sequence, but they underscore the complexity of translating philosophical ideals into practical reality. By recognizing both the intrinsic and instrumental value of liberal education—that is, seeing self-shaping as inherently worthwhile and practically useful—we might strike a balance between Brann's ideal and our contemporary world's demands. This balanced view could make the Brann Sequence not only more desirable but also more viable.

The Brann Sequence in practice

At the heart of the Brann Sequence—“first shape yourself, then society”—lies a paradox: Can one truly shape oneself without also engaging in and shaping society? Or are self-shaping and societal engagement inherently intertwined?

Brann's approach emphasizes deep engagement with Great Books, often divorced from immediate practical application. In fact, she cautions against "the dismal currency of relevance," suggesting that true self-shaping stems from grappling with timeless ideas rather than fleeting current events. This perspective implies that meaningful self-development can occur in relative isolation from active societal engagement.

However, this raises a crucial question: How can one truly appreciate or recognize greatness without experiencing its absence? The ability to discern great from not-great arguably requires a breadth of experience, including exposure to works and ideas that may not meet the standard. Some significant level of broader engagement, including with society at large, might be necessary for effective self-shaping.

Plato's cave myth provides another illuminating perspective. The freed prisoner's experience in the world of shadows proved crucial for later recognizing the sun as "the cause of all the things that he and his fellows used to see" (516c). This suggests that our initial—perhaps narrow-minded—engagements with society are necessary for us to later recognize and appreciate deeper truths. Viewed this way, isolation from societal engagement during the self-shaping process might actually hinder, rather than help, our development.

The nature of learning itself, as described by Michael Oakeshott, challenges the linear progression implied by the Brann Sequence. He describes learning as "an endless unrehearsed intellectual adventure," but he goes even further in characterizing human life:

It has no preordained course to follow: with every thought and action a human being lets go a mooring and puts out to sea on a self-chosen but largely unforeseen course. It has no preordained destination: there is no substantive perfect man or human life upon which he may model his conduct. It is a predicament, not a journey.

This view presents learning and life not as predetermined paths, but as unpredictable voyages of discovery. If human existence is indeed a "predicament" rather than a journey with a fixed destination, can we realistically expect individuals to complete a discrete phase of self-shaping before engaging in societal shaping? Oakeshott’s perspective suggests that self-understanding and societal engagement develop concurrently, each informing and shaping the other. While this dynamic approach doesn't negate the value of focused self-development, it does challenge the strict separation implied by the Brann Sequence. The neat, linear progression from self-shaping to societal engagement may be more idealistic than realistic.

While Oakeshott emphasizes the unpredictable nature of learning, Brann's approach to liberal education offers a more structured path, albeit one that acknowledges the transformative and often humbling nature of deep study. She references how students at St. John’s College “come knowing nothing and leave knowing that they know nothing,” which she sees as a crucial step in the journey of self-shaping. True self-knowledge involves recognizing the vastness of human knowledge and the limitations of one's own understanding.

Paradoxically, the realization of I know that I know nothing may itself require more than superficial societal engagement. It's often through grappling with real-world complexities, rather than merely encountering diverse perspectives in theory, that we truly recognize the limits of our understanding.

The outcome of intensive self-shaping—a recognition of one's own ignorance—might be ill-suited for inspiring societal engagement. This approach risks inducing a paralysis of action, where individuals perpetually feel unprepared to meaningfully shape society. Such hesitation, born from heightened self-awareness, could ironically impede the very engagement that is meant to come after self-shaping.

Another critical question emerges when considering the viability of the Brann Sequence: At what point is shaping oneself sufficient for then shaping society? Is it possible to define a minimum self-shaping threshold?

While superficially appealing, measurement of this kind seems misguided. Any fixed criteria risk overlooking the deeply personal, ongoing, and endless nature of self-knowledge. Instead, we might conceptualize self-shaping and societal engagement as a dynamic, iterative process in line with Oakeshott’s thinking. This approach acknowledges that while some level of self-shaping is necessary before meaningful societal engagement, the two processes are inherently intertwined and mutually reinforcing.

Brann’s reluctance in making the dynamic relationship between self-shaping and societal-shaping clear makes me wonder if she genuinely advocates for societal shaping as a distinct phase. We know that she is primarily concerned with individual development and fulfillment. For her, the value of self-shaping through liberal education lies not in its potential for subsequent societal impact, but in its inherent worth to the individual. While she does mention interfering judiciously in society, this seems almost an afterthought compared to her extensive discussion of self-knowledge and understanding.

I’m not convinced that self-shaping without truly embracing societal shaping is a tenable position, and in fact may be damaging to the project of liberal education. Acknowledging the instrumental value of a liberal education in addition to its inherent value seems like a more viable option. Seeing it as both a utility and a means “lived for its own sake” can strengthen its case. It’s the equivalent of, in Plato’s terms, recognizing the immense value of “seeing the good” and the importance of bringing that wisdom back “to bind the city together” (520a).

While economic pressures and the fast-paced nature of technological change pose challenges to Brann’s vision of liberal education, they paradoxically underline its relevance — the “dismal currency” that Brann wants nothing to do with. In an era where artificial intelligence is at the cusp of reshaping the social structures we take for granted, the need for individuals capable of thinking beyond immediate consequences has never been more acute.

The economic reality of high educational costs and student debt creates pressure for immediate, tangible returns on educational investment. At the same time, the rapid evolution of technology means that specific technical skills quickly become obsolete. These factors may seem to favor specialized, career-focused education over Brann’s model of liberal education. However, it is precisely this volatile environment that calls for the kind of flexible, foundational thinking that liberal education fosters. The ability to grapple with fundamental questions and to think critically about human nature are increasingly valuable in this time between worlds.

Notably, there is a conspicuous absence of individuals experienced in philosophical inquiry occupying positions within the technology startups and companies that are actively shaping our society. This gap points to a critical need for integrating liberal education with technological expertise. The challenge, then, lies not in choosing between the process of self-shaping and the skills needed for shaping society, but recognizing their inseparability. How can we create educational models that honor the depth and breadth of liberal education while also inspiring and preparing individuals to engage meaningfully in shaping our world?

Integrating self-shaping and societal engagement

Through this examination of primarily Platonic and Brannian ideas, we've seen that while the “shape yourself, then society” sequence is philosophically compelling, it faces significant challenges in practical implementation.

The inseparability of self-shaping and societal engagement, particularly in our rapidly evolving technological landscape, calls for a more dynamic model of education. Rather than viewing them as distinct phases in a linear pattern, we might think of them as intertwined cyclical processes with the potential to continually inform, influence, and enrich each other. This perspective allows for an ongoing focus on self-development while acknowledging the need for informed societal participation.

A path forward may lie in integrating liberal education with technological expertise, combining the depth of studying great works through philosophical inquiry and the practical skills necessary to participate in the modern economy. This approach, over time, could address the underrepresentation of individuals versed in philosophical thinking within the companies shaping our future.

As we move forward, we must grapple with several unaddressed questions:

• How can we create educational environments that cultivate both deep reflection and practical engagement with societal issues?
• What role might emerging technologies play in enhancing the self-shaping process?
• How might a deeper understanding of oneself, and by extension human nature, lead to more thoughtful and beneficial technological innovations?

Reflecting on my journey from tech entrepreneur to student of philosophy, I've come to appreciate the value of both practical skills and deeper contemplation. As we navigate the complexities of our age, perhaps the most crucial skill we can cultivate is the ability to continually and deliberately shape and re-shape ourselves. In doing so, we will recognize that shaping society demands the same care and attention we devote to shaping ourselves.