Grappling with the big questions

cultures of agency, flourishing communities & institutions, AI & self-expression

Oct 07, 2024

Last week, I shared some life updates on what I’ve been up to. This week, I’m sharing a list of big questions that serve as my compass as I grapple with the theory of flourishing and actualize it through building a modern town square.

Historically, I’ve unconsciously allowed societal expectations to drive the work I did and the ambitions I pursued. Now, I think of my career less as a series of milestones to achieve, ladders to climb — more as a set of experiments to run, projects to progress.

To structure these experiments and projects, I sat down last month as I began my masters in applied positive psychology to articulate what questions I planned to center my explorations around.

My intention is not only to answer these questions at the theoretical level through writing, but also to wrangle with them tactically over the course of building The Commons, a community space in San Francisco dedicated to meaning making and self-expression, and through other future projects.

These are the big questions I’m grappling with and hope to answer over the span of my “career.”

🔭 Cultures of Agency

What are the structural conditions needed to seed a culture of individual and collective agency within an institution or a community?
What factors have contributed to the presence of agency in certain communities throughout history? What role do community institutions play in fostering human progress?
What new narratives can we create around our relationship to work, “economic value,” and true ambition?
What can we learn from the history of the Bay Area to understand the conditions that have enabled agency to permeate the region?

My interest in exploring agency centers around the core belief that there’s no character trait more essential to individual and societal progress than agency. Agency is the embodied conviction that you have the power to create meaningful change in your life and transform your vision into reality. It’s the engine that powers human progress.

I’m interested in the historical and cultural evolution of agency, particularly in regions like the Bay Area where it’s deeply ingrained in the social fabric. My hypothesis is that the agentic nature of the Bay Area was seeded decades ago and shaped in large part by the formation of America.

In the early days of our nation, the most risk-tolerant immigrants set sail across the Atlantic in search of economic opportunity, religious freedom, and a better life. They held onto the optimism that life would be better in the New World. As our young nation found its footing, society in the original colonies set the tone for early American life while westward expansion came to symbolize even greater opportunity and mobility.

In the mid-19th century, the allure of the Gold Rush drew many of the most entrepreneurial Americans to continue west in pursuit of wealth and reinvention. Call it naivety, greed, or a spirit of agency, the founding settlers of the Bay Area were fueled by an unrivaled level of courage and tenacity.

The region became home to those who embraced risk and innovation, establishing the roots that would shape the DNA of the modern day Bay Area. In the ensuing years, it has served as a crucible for alternative living and movements that swept the nation — from the Free Speech Movement and hippie counterculture movement in the 1960s, to the farm-to-table movement in the 1970s, to the birth of modern technology throughout the 20th century.

Decades later, agency remains on full display with the Bay Area being the center of technological innovation and San Francisco being home to a fifth of all US startups.

Inspired by a city that lives at the edge of tomorrow, I want to uncover the conditions we need to usher in more cultures of agency to foster individual and community progress.

🏛️ Flourishing Communities & Institutions

In the face of the meaning, loneliness, and meta crises, how can we reimagine and build the town squares and secular churches of the 21st century in support of collective flourishing?
What are examples of flourishing societies from the past that enabled the pursuit of truth and human progress? What are the core elements of systemic flourishing? What’s the role of the individual versus the collective?
What were the conditions that allowed individuals like Benjamin Franklin to establish the new age institutions (Penn) and civic organizations (juntos, libraries, philosophy societies) of his time?
What’s the history of clubs and extracurriculars? How have they contributed to meaning-making and identity formation at the individual and community level?
What’s the role that societal rituals play in meaning and purpose-making?
How can we advance the psychology of progress and integrate individual psychological healing as part of the course towards societal progress?
How can we redefine what it means to gather in community and center around deep connection, aliveness, and introspection? How has the role of hosts and community organizers evolved over time?

Benjamin Franklin, the visionary behind many of America’s earliest civic institutions, conceived a number of our nation’s firsts in his Junto, a discussion group where he convened with fellow intellectuals, artisans, and tradesmen to contemplate solutions to concerns of their time. Among the ideas were our nation’s first lending library, our first hospital, one of the original volunteer fire departments, and an intellectual society.

Societal progress is born from the imagination of an individual, but is actualized through collective effort.

Nearly 300 years ago, Franklin and his contemporaries laid the groundwork for what would become the fabric of daily life in modern America. Today, as we confront the meaning and loneliness crises, along with broader systemic challenges, we have the opportunity to reimagine and reshape our modern institutions to better support collective flourishing.

Never doubt that a small group of thoughtful committed individuals can change the world. In fact, it's the only thing that ever has.

— Margaret Mead

This set of questions is driven by the notion that systemic flourishing begins with the individual. Flourishing looks different for each of us because it’s about coming home to ourselves. For a community to flourish, each individual must be on their own path towards coming home to themselves. Can we truly flourish if those around us are suffering?

I flourish in the moments when I’m in deep presence and feel connected to the grander scheme of it all. I’m operating consciously and freely self-expressing. Whether I’m writing, working on a meaningful project, hiking in a national park, or spending time with a friend, it’s a feeling of coming alive and being moved by the honor to live this life. These moments are marked by flow and a feeling of being deeply integrated. It’s a homecoming, a grounding, an expansiveness, an easefulness, a peacefulness.

It’s clear to me that others are flourishing when they come alive in ways that give me a lens into who they were when they were children, overflowing with unbridled curiosity, wonder, and excitement. They exude a level of agency and passion that is infectious.

It will take a collective narrative shift and it’s not just up to us to answer these questions alone. We need institutions to support us in this process.

As church participation continues to decline, we can no longer rely on our traditional institutions for meaning-making. More than ever, we are in dire need of new institutions and communities that can guide us in our unfolding and becoming.

That’s precisely what we intend to experiment with and build at The Commons.

🪄 AI & Self-Expression

Assuming that advancements in AI free up humanity to self-actualize, how can we create social infrastructure and design institutions to support humans in unfolding into their fullest self-expression?
How will AI elevate human self-expression and agency?

We have early indicators that the commercialization of AI will revolutionize our relationship with work. While I love a good optimistic take, I often hear unwarranted confidence that as AI begins to replace our existing jobs, we’ll have the freedom to find work that’s more aligned with our life’s purpose. This assumes that we’re all in tune with our higher calling — something that’s often subtle and easily suppressed.

After spending the last two years exploring my (previously unhealthy) relationship to work, diversifying my sources of meaning, reconnecting with my self-expression, and refueling my ambition, I sense we’re closer to a full-blown meaning crisis than a liberation.

As a society, we need to step back and reflect on who we want to become once AI automates much of the work that has historically provided us with a sense of purpose, worth, and identity.

If you’ve ever had the opportunity to offboard from a company as your role was being deprecated or backfilled, you know the reality that our contributions fade with time, if not as soon as we move on. Someone replaces us, work is redistributed, life goes on. Regardless of how hard we fight it, we are all largely cogs in the corporate machine.

What is worth fighting for is our liberation from the notion that our worthiness is solely tied to work that generates economic value. Cultivating experiences of self-expression to better understand ourselves and discover who we are beyond merely value capturers will help us gain clarity on who we might become in a post-artificial general intelligence (AGI) world.

Supporting our members in reconnecting with and harnessing their self-expression is another central pillar of The Commons.

And so there you have it, the big questions I’m grappling with in this season of life. I’m certain that these questions will evolve and expand over time.

If you’re exploring similar questions in your work, I’d love to hear from you in the comments or say hi on Twitter :)