“Imagine Princeton as your training ground,” said Eddie Glaude, who had just joined the University’s faculty as an Associate Professor in the Department of Religion and Program in African-American Studies.

It was nearly a quarter century ago, and I was more than halfway through my undergraduate years, but Professor Glaude’s off-hand comment at an evening event in Wilson College struck me then, and has stayed with me since.

On the heels of 9/11, my classmates and I were restless, I think, and I was naïve, to be sure… looking to change the world.

“Serve here, master this place, first,” Professor Glaude counseled. “Let this place - its imperfections, its inspirations - be your template for all places.”

“Really?” I thought. “Princeton, New Jersey?”

In the decades since, I’ve tried responding to his call to see - and serve - the world through the prism of place: first, as an overly earnest campus “leader” who took himself too seriously, and in later years as a civic entrepreneur in Appalachia, foundation director in Detroit, and technology executive in Asia Pacific - one who actively chose to live and lead both in the American heartland and abroad... striving to be in markets, and of places.

Sure, contemplating and constructing a career on the basis of place has offered me a cleaner way to land otherwise-abstract corporate and civic metrics with more clarity and meaning… whether the deliverables in question had to do with customers converted and citizens connected or centered on market share and community care.

In that way, place can be a useful - and, often, hugely sharpening - unit of analysis.

But living and leading in place also taught me the market - and civic - value of attending to more than spreadsheets or slides can capture: the “soul of communities,” the stories of their days, the spirit of their times.

After all, here’s a hard truth in our age of career-by-LinkedIn: no matter your company or cause, have you really realized your full potential - with nothing left on the table - if you haven’t found your way into the zeitgeist of… a place? Be it near or far.

These days, I wonder: do Professor Glaude’s words carry new weight - and wisdom - in this age of AI and geopolitical shifts? At a time when people across sectors and seasons of life are dazzled - but burdened, too - by opportunities to master it all, with breadth, what if a more enthralling, stabilizing and caring path entailed mastering just a place, with depth?

Yes and yes.

Irish novelist and poet James Joyce was right when, a century ago, he remarked: “In the particular is contained the universal.”

Of late I’ve been moved by the breakthrough logic that undergirds AI: in their pretraining phase, large language models are exposed to vast numbers of “particulars” and trained, again and again, to predict what comes next. And yet, at scale, from these particulars, they begin to exhibit something like generalization - and even flashes of the universal.

What can - what should - this “power of the particular” teach us about how we humans learn - how we train, and pretrain? In a world striving, but struggling, too, to realize its caring potential - not to mention its approach to cultivating future-proof human skills at global scale - might answers lie within our immediate line of sight? Literally.

“If I can get to the heart of Dublin, I can get to the heart of all the cities in the world,” Joyce said, too. What if each one of us committed to getting to the heart of a place this year? Our hometowns, headquarters or far-flung communities we’ve otherwise “othered.”

Over the years, some have assumed my own experiences getting to the heart of places - as a policy leader for College Summit in Washington, a partnerships leader for Google in South Asia, a social entrepreneur and philanthropist in Michigan, a business leader for Twitter, Times Bridge and OpenAI in the Global South, and a humanities and higher education leader in Virginia and beyond - has entailed a kind of constant context switching.

Far from it.

In truth, it’s actually felt more like the harnessing of a single, place-based (er, place-obsessed!) sensibility: that is (1) first, the cultivation of a sensitivity to understanding a place’s past and promise; then, (2) the seeing and mapping of a place’s topography, its town squares and its leading voices; and then (3) finally, the narration of a breakthrough story with - and not to - usual and unusual suspects in place.

Surveying Detroit’s landscape of power and purpose taught me how to approach the people and promise of Twitter. Constructing a delicate approach to helping global missions realize influence in New Delhi helped shape my approach to helping storied American institutions open their doors to new ideas. The dots connect.

Purpose, potential and progress - from business buzzwords to social impact feel-goods - flow downstream from seeking and seeing place, I’ve discovered, and not the other way around.

As technology professionals, policymakers and philanthropists usher in a new era of experiences - to advance learning, to advance listening, to advance leadership and (gulp) to advance peace and understanding in this time - perhaps under our noses lies the starting point, and the planet’s most transformational curriculum of all: place.

It’s why I’ve tried to center place-based education and experience in some of my own missions of late, one of which seeks to harness the power of the particular to build bridges, and new capacities, in this AI-ascendant era.

I’m not alone in having awakened to the singular power that place-seeing, place-mapping, place-making have to offer us. Dr. Fei-Fei Li, known as the “Godmother of AI” whose work on ImageNet helped catalyze modern computer vision, argues in “The Worlds I See” that perception - and especially vision - sits near the heart of both machine learning and human understanding.

So, what if our culture imagined “sightseeing” as a pressing - and sacred - obligation? Through this lens, both civic engagement and a more immersive kind of cosmopolitanism take on new meaning.

It’s why, I think, de Tocqueville marveled two centuries ago at a young American republic’s commitment to place-based… everything. And why today, I marvel at so much: from Knight Foundation’s commitment to American places and National Geographic’s education-and-explorer ecosystem to the Teton Science Schools’ place-based experiences inspiring curiosity, Virginia Tech’s Creativity and Innovation District drawing attention to a new kind of geography and The Huntington’s reminder that transformational places, at their best, are communities of the curious.

But still, unseen places are all around us.

Professor Glaude, who remains at Princeton, has in the years since published scholarship on a range of themes, including “Begin Again,” a book dwelling on the writer James Baldwin. In it, he - Dr. Glaude - writes that Baldwin argued “to live and move about the world without questioning how the world has shaped and is shaping you is, in a way, to betray the gift of life itself.”

Might 2026 be the year we begin to see places not just as meaning-making machines - where, yes, we see beauty, hear story and make memory - but also as sources of a new kind of teaching, training and trust-building superpower?

A superpower that trains - and, if you’re an AI, pretrains - us in the seemingly-flat particulars of place… particulars that ultimately give rise to peaks from which we see the universal.

I wasn’t walking alone, nor was I with family or old friends; I was traversing the path of Pickett’s division with fellow working professionals of all ages from around the country: non-profit leaders, lawyers, physicians, consultants and young graduates still finding their way. And I myself was the CEO of an international investment firm I’d launched years earlier drawing on a decade of executive experience at Google and Twitter in the U.S. and across Asia Pacific.

Our fearless leader and teacher that day - indeed for a few days that week - was renowned Civil War historian James McPherson, the author of the Pulitzer-prize winning Battle Cry of Freedom.

Sure, most of us were alumni of Princeton University, where Professor McPherson has long taught and I’d previously served as a Trustee. And, yes, we were participating in “Princeton Journeys,” a program designed to strengthen bonds between alumni and their alma mater.

But, still, while I finished an e-mail and watched a perspiring, out-of-breath Fortune 500 executive lead a Zoom call as we traced the topography towards Cemetery Ridge - and Professor McPherson reflected with great poignancy on the test and toll of that early July day in 1863 - I couldn’t help but wonder:

“Why are we all here, and what, exactly, are we pursuing?”

Nearly three months earlier, in the early hours of February 3, I left my home in Charlottesville, where I’d lived for four years, and drove south through the Shenandoah Valley and up the Blue Ridge Mountains towards Blacksburg, the home of Virginia Tech.

On my mind as I drove through a freezing-rain-fueled “wintercane” of sorts was, mostly, a yearning to learn, and grow.

In recent years, and undoubtedly accelerated by the Covid pandemic, I’d begun seeking out a steady stream of education and experiences - online and offline - to scratch a learning itch I didn’t quite know how to explain. Friends and acquaintances around the country seemed to be traveling in similar learning lanes, too. Maybe it was behavior confined to my bubble or, maybe, we were among millions nationwide who, according to Pew Research, had by the pandemic begun racing towards platforms like Coursera, Khan Academy, Stack Overflow, YouTube and others as learners.

What kind of ailment were we treating while trading texts about PBS features on spacetime, MIT OpenCourseWare lectures on machine learning and podcasts centered on the afterlife of Ancient Greece? Why did growing numbers of friends from across a range of pursuits seem to seek refuge - and nourishment - in short-burst learning excursions convened by the Chautauqua Institution and the Aspen Institute? If “biohacking” rose to the fore during the health-and-well-being scares of Covid, what were we hacking: digital literacy? Or a kind of human literacy? It felt like a self-medication of sorts and, frankly, I wasn’t sure it was meeting the mark.

Having dropped out of business school more than a decade earlier, I often wondered, “Should I finally get that Master’s or Executive MBA? Maybe a law degree? A Ph.D., even?” Needless to say, my kids grew wary of my off-and-on back-to-school ruminations.

So, when Dr. Sylvester Johnson, one of the nation’s leading scholars of African American religion and, then, the director of Virginia Tech’s Center for Humanities, asked if I’d like to spend a few hours on campus learning about the university’s growing commitment to the humanities, I thought, “Why not?” After all, he and I had served since 2019 as board directors of Virginia Humanities, one of the nation’s 56 humanities councils and I, a college history major who’d built a career as an entrepreneur and executive in technology, had grown to believe the humanities needed to evolve a refreshed posture in our inescapably digitally-dressed world.

I’d never been to Blacksburg before. I’d loosely heard of it through former Google Chairman and CEO Eric Schmidt, a mentor who had two decades earlier recruited me to serve as his speechwriter. Eric grew up in the small mountain college town on the Eastern Continental Divide in the ’60s and ’70s. “A chance to connect the dots,” I thought.

I arrived late - and wet - for breakfast with Dr. Johnson. “What did I miss?” I asked, smiling, recalling the song from Hamilton featuring Thomas Jefferson.

But by the time I left Virginia Tech, inspired by the institution’s motto - “Ut Prosim” (That I May Serve) - I was asking a different question on the ride home as the rain subsided and the skies cleared: “What if I took a career detour to build the humanities-centered, science-curious lifelong learning experience I’d long been in search of?”

Earlier this year, nearly three years to the day after walking Pickett’s Charge, I found myself walking a different military site, with a different historian and a different group of lifelong learners: at Arlington National Cemetery with Dr. Paul Quigley, director of the Virginia Center for Civil War Studies.

On our walking tour was the graduating Class of 2025 of the Virginia Tech Institute for Leadership in Technology, which I’d founded two years earlier to offer the nation’s first mid-career degree in the humanities to learners and leaders from across fields and functions, a first-of-its-kind lifelong liberal arts credential with an eye on both the timeless sensibilities of the arts and the timely skills of our AI age.

We were in Washington to celebrate the graduation of this group of students from our one-year program, one which by then had drawn fellows from five countries, ten states and two-dozen companies and causes ranging from cybersecurity to conservation.

Together, each year, they had studied history and philosophy, engaged with literature and creative writing and immersed in place and faith - with an eye, too, on the origins of artificial intelligence, and its opportunities.

Students had read and written about scientists Bohm, Einstein and AI pioneer Fei Fei Lee, but also texts from 9^th-century China, tales from Elizabethan England and a letter from a Birmingham jail. Their guest speakers had ranged from National Geographic Board Chair Jean Case and former Howard University President Ben Vinson to venture capitalist Katie Stanton and “Father of the Internet” Vint Cerf.

And along the way, I myself had spent a year working with OpenAI, helping guide the company’s entry into India and emerging markets, and served as Chairman of the National Humanities Center.

“A dream realized,” I thought, as I took in afternoon views of our nation’s capital, and of President John F. Kennedy’s grave, from Robert E. Lee’s Arlington House. “How did we get here?”

While this story culminates in Southwest Virginia, from where we ultimately envisioned, entrepreneur-ed and evangelized a more capacious, current and connected vision for the humanities and lifelong learning, the story begins, I think, in Philadelphia and an unseen but self-evident truth expressed at our nation’s founding in 1776.

In that summer 249 years ago, the Founding Fathers invoked bedrocks of American self-governance in the Declaration of Independence, and included “the pursuit of happiness” as an inalienable natural right, alongside life and liberty. But what exactly did they mean by “happiness”?

Were they referring to matters of the hearth, namely property and economic fulfillment? To matters of the heart, including the cultivation of a kind of inner peace and tranquility? Or did they, with an eye on an ever-evolving nation, have their gaze elsewhere?

As I was rekindling my commitment to the humanities, I wasn’t the first to wonder.

Indeed, scholars have been weighing in on this question for years, as have storytellers. One - the filmmaker Ken Burns - has been particularly articulate and affecting for me as I grew to understand that recasting the humanities to realize a new, future-proof dynamism in our culture might constitute an act of reclaiming our revolutionary roots, too. Burns, whose latest film The American Revolution premiered last month, recently appeared on CBS’s Face the Nation and was unequivocal in his sense of what happiness “pursuit” the founders had in mind:

“Lifelong learning,” he said.

“The pursuit of happiness is not the acquisition of things in a marketplace of objects, but lifelong learning in a marketplace of ideas,” Burns continued. “To continually educate yourself is what was required to sustain this republic and I think that’s what we’ve gotten away from.”

Jefferson, the Declaration’s lead author and a student of the Enlightenment, long situated happiness with learning, and was known to keep and recommend extensive reading lists for self-improvement. He wrote in his later years: “I look to the diffusion of light and education as the resource most to be relied on for… advancing the happiness of man.”

Burns is not the only contemporary I came across who emphasized, emphatically, the Founders’ belief in lifelong learning, and personal transformation, as essential, and even existential, to the American experiment.

Scholar Jeffrey Rosen, the author of The Pursuit of Happiness, has also highlighted the Founding Fathers’ emphasis on personal self-mastery as a necessary path to personal and political happiness. “...Happiness requires a life devoted to the pursuit of self-improvement so that we can be our best selves and serve others,” Rosen remarked at an event convened last year by the National Constitution Center, where he serves as President and CEO.

“So moved,” I’ve said to myself over the years as I’ve heard voices reflecting on what Walter Isaacson calls “the greatest sentence ever written,” the topic, and title, of his book published on November 18.

“But how might we gauge where we are as a nation today?,” I’ve wondered, too, including on that early 2022 drive to Blacksburg. “And if, as Burns argues, we’ve ‘gotten away’ from this spirit, what might we do to move forward a nation-scale, always-on culture and capacity of lifelong learning on the eve of 250 years of American independence?”

My family and I did move to Blacksburg, and the old, elder mountains of Appalachia, in the summer of 2022, and I joined the faculty of Virginia Tech as a Professor of Practice and Distinguished Humanities Fellow.

Struck immediately by the big, mountain-rimmed skies of our town, and the blue-sky, bottoms-up spirit of experimentation and entrepreneurship that permeates the university, the atmosphere seemed ripe for wrestling with big questions, and big answers. What seemed to be in the air then were questions, accelerated by Covid, about how the humanities might recover from enrollment declines and how higher education might rediscover its pre-pandemic value proposition. What we didn’t yet know was we were on the precipice of a zeitgeist set to be consumed by large language models - and equally large questions about learning, living and leading.

“What singular contribution could I make from within higher education,” I thought, “with an eye on the natural right of lifelong learning as a North Star?”

My initial, cursory glance at institutions in the business of higher knowledge presented, it would seem, a cloudy picture. After all, confidence in higher education has fallen drastically in the last decade, enrollments in the humanities are declining, Ph.D. pipelines are thinning, and baseline interest in graduate programs may be softening, too.

But, the entrepreneur in me wondered, notwithstanding this murky picture of higher education, what might a portrait of higher learning reveal? Bluer sky, I found.

Nearly three quarters of U.S. adults call themselves lifelong learners, more than half of Americans on YouTube report having used it to learn how to do new things, nearly nine in ten podcast-listening Americans say they do so to advance their learning, and 60% of adults say they use AI for “self-directed learning.” What should we make of all this?

Yes, we live in an era of deep, disheartening division and distance, I thought, but we also live in an era in which Americans seek and strive to learn on their own and from one another - synchronously and asynchronously - in transformational ways. The depth and breadth of wisdom available in the marketplace of ideas - and wisdom being tapped, citizen-to-citizen, prompt-by-prompt - is awe-inspiring and worth building from, not breezing past.

Sure, some among us may be quick to regard much of this activity as unsophisticated noise. But, I wondered, what if we actively choose - as my former Knight Foundation colleague Trabian Shorters reminds us when championing asset-framing as a singular cognitive skill - to detect positive signal in this noise? This attitude of seeing the learner and leader in fellow citizens can be profoundly shape shifting: it’s what, fifteen years ago, on the heels of the Great Recession, inspired me to co-found Michigan Corps and Kiva Detroit, online civic-engagement platforms cultivating the citizen - indeed, the learner and leader - in everyone committed to these places. “Ask what you can do for your state,” we proclaimed.

After my leap-of-faith move to Blacksburg, here’s a question I began to ask in higher education circles: in an AI-leading nation in which credentials themselves are being called into question, what should we make of the fact that microcredentials - more than 1 million and counting in the marketplace - are booming?

It would be easy to rest on these little laurels.

Headwinds abound in higher education, yes, but the marketplace is responding to fill the gaps, isn’t it? After all, big technology companies like Amazon, Google, Microsoft and OpenAI have committed themselves - including at an event convened by the White House in early September - to a new wave of must-have technology training. If the 2010s were marked by efforts to evangelize coding, albeit with mixed success, this decade should, it would seem, center on expanding AI literacy. Right?

Elsewhere, in both the public and private sectors, efforts to reimagine and refresh learning at all levels abound, too, including at the National Humanities Center and Transcend Education, whose boards I serve on. Thousands of flowers are undoubtedly blooming.

And at our universities, some might suggest business, education and public policy schools have long been adequately filling lifelong learning gaps. After all, for the better part of a century they have inhabited the language of leadership education, offered bespoke upskilling experiences for professionals and developed revenue-generating practices centered on helping companies evolve their respective workforces. Many have grown an appreciation for the value of soft skills, too.

And outside of professional schools, universities - via continuing education divisions - support a wide range of customers seeking more immediate growth and know-how, as well.

So why offer a fix to what doesn’t seem broken?

Because here’s another self-evident truth, one which Burns gestured at: considering the trend lines around how young people view school and college, the state of our civic discourse, and growing economic pessimism, it’s also plainly clear a nation-scale, institutionally-reflected, politically-prioritized spirit of lifelong learning has not taken hold.

Perhaps in offering a multitude of training experiences for organizations centered on immediate learning outcomes, higher education has overlooked the cultivation of a lifelong learning movement among individuals centered on the intrinsic value of learning itself.

I didn’t know precisely what to do, but I did know that the humanities needed to enter the chat.

“The acronym ‘STEAM’ doesn’t seem to do justice to the role of the liberal arts, does it?” I asked Scott Hartley, the author of The Fuzzy and The Techie, while standing on stage at Virginia Tech’s Haymarket Theater on a cold winter morning in February 2023 alongside university president Dr. Timothy J. Sands.

I was making reference to a once-pervasive acronym that places the “arts” at the center of the ever-more-pervasive “STEM” fields of science, technology, engineering and mathematics.

“No, you’re right” Hartley replied. “We need something more coherent – and compelling.” He paused for a moment and then asked the two of us: “How about ‘full stack’ human?”

“That’s it!” I said, before rushing to introduce Hartley and Dr. Sands to the audience gathered for their fireside chat to conclude our second annual Humanities Week. I knew immediately this frame - “Full Stack Human” - had the substantive and storytelling value the landscape, and even my inner discourse, needed. It might even strike a chord with both humanists and technologists given their shared affinity for “stacks” of one sort or another.

As I took my seat, I wondered, “What does the ‘Full Stack Human’ of the future look like, and what might it mean to see human flourishing through the prism of a full stack?”

Together with Hartley, I imagined a three-layer stack: (1) undergirded, as infrastructure, by the timeless introspection, intuition, and imagination the arts and sciences trigger; (2) built upon with an appreciation for the kind of entrepreneurship - and evangelism - it takes to break through with one’s calling; and (3) topped off by timely fluency in today’s technology trends, whatever they may be.

If the gravitational pull of our culture, today, pushes us towards the top of the stack, a layer that is constantly in flux, could we - inspired by our Founding Fathers, and the quiet experiences of many lifelong learners - recast the humanities as inhabiting its foundational layer?

By the spring of 2023, a year after walking Pickett’s charge in Gettysburg, I resolved with conviction, “If I build it, they will come.”

With the support of Virginia Tech, I launched our Institute for Leadership in Technology that summer, offering the nation’s first leadership degree grounded in the humanities - and first-of-its-kind lifelong liberal arts credential - to rising leaders coming of age in this time of generative artificial intelligence. Immediately, many hundreds from around the world reached out to say, “Yes, finally!”

Since then, each year our group of learners from a range of communities, companies and causes engage together on questions of what it means to be human, and reflect on what it means to be a learner and leader across the “full stack.” They do this not to serve immediate ends, but to serve higher learning itself, and the other-centric - and, our Founding Fathers might argue, happiness-inducing - muscles of higher leadership that the pursuit of knowledge for knowledge’s sake cultivates. It turns out curiously immersing oneself in learning the timeless because it has essential value can buttress one’s life - and leadership and learning practice - in a culture already saturated with pressures to lean into on-demand timely technical learning.

Now in our third year, we have hosted leaders from companies in Silicon Valley and the Shenandoah Valley, entrepreneurs championing causes ranging from oral history to public-interest technology and public servants with experiences in aerospace engineering and national defense.

At a time when institutions nationwide are confronting interrogating headwinds, our Institute is as of this year not alone in suggesting that new tailwinds - and new constituencies - might be generated by embracing the creation of lifelong-learning bridges for more of our fellow citizens, bridges whose mission is the cultivation of a commitment to learning for learning’s sake.

This past summer, both the State University of New York at Potsdam and Northeastern University President Joseph Aoun began to advance lifelong learning paradigms, too, inclusive of the humanities.

I’ve wondered often, particularly this year, “What if navigating these heady times for institutions of higher learning included, first and primarily, seeing and serving a nation of unseen and unmet learners? What if the vitality of higher education’s knowledge-seeking mission rests on the vigor it brings to its knowledge-imparting mandate? And what if lifelong learning evolved from a module that is incidental and improvised - housed in this or that school - to a mission that is integral, intentional and inspired, with newfound appreciation for the centrality of the humanities?”

Yes, I’ve grown to believe, universities must continue to offer one-way bridges that meet learners of all ages with programs that enthrall and educate instrumentally: with tools of the trade; entrepreneurship know-how; and AI mastery. But we also need two-way bridges that meet learners where they are not just with an eye on retraining and refreshing employability, per se - but with a more complete, inspired posture that, first, sees and salutes an existing learned spirit, and situates and storytells it as a civic virtue. And then, critically, offers education and experiences that emphasize learning-for-learning’s-sake as the quintessentially-American leap of faith.

Here, the institutional humanities can lead with urgency as the foundational layer of what it means to be a “full stack” human, reminding us of their particular power to nourish the soul, humble the mind and stretch the length, and depth, of human purpose.

Beginning 2023, while pitching my Institute to anyone that would listen, many would ask: what precisely are the humanities? Which departments are in? Who’s out? I crafted a six-word poem to capture a new, capacious essence:

Awe and wonder

In the other

In our culture of immediacy and the instrumental, education and experiences that cultivate a lifelong spirit of awe and wonder in human, and non-human, others - past, present and future - may not just be the antidote to what ails us, but the universal aspiration our Founders intended.

What could be more apropos ahead of 2026 and America’s semiquincentennial?

Many universities ask me to reflect with them directly on opportunities to refresh their approach to humanities education and evangelism. I often begin by asking, “What might a university founded today, one which takes seriously both advanced research and accessibility to learners across the full stack, look like?”

On the heels of Burns’ documentary and on the eve of America’s 250th, a more inspired starting point for institutions of higher learning, and indeed all public institutions, might be to first reflect with more depth on the hidden, happy pursuit in our nation’s founding document:

First, by seeing in our Declaration of Independence an emphatic declaration of our inalienable natural right to a vibrant - and lifelong - flourishing of the mind. What if this was a sacred American ideal, and one which sat at the center of our national sightline? Indeed, sitting with this truth before stirring to action is essential. Considering the way our Declaration’s writers situated happiness with learning and it with civic virtues, imagine our Constitution - whose 227th anniversary we celebrated this past Constitution Day - opened with: “We the Learners”?

Second, by speaking of and storytelling the learners among us as pursuing among the most noble, and quintessentially American, of civic duties. When we see and celebrate the lifelong learners among us on stages big and small, we have the beginnings of culture change. I’ve found language matters, too: well-intentioned headings like “professional development” and “upskilling” can downplay the profundity of what self-improvement constitutes. Our civic culture, and universities, can no longer afford to leave the rise of this permission structure, one which assertively lifts up lifelong learners to the top of our city on a hill, to chance.

And finally, by shaping concrete bridges of opportunity into lifelong learning for all Americans, no matter their season or station in life. This would entail reflecting on how learning happens in an AI-ascendant era, what is to be learned and what initiatives need our recommitment – and which need reimagining. Such bridge building will rightly compel institutions to rise and wrestle with hard questions. Here’s one: what is American excellence, and the quintessential American metric? Only the view presented by majors and minors, Ph.D.s and placements? Or the broader vista featuring learners, askers, seekers, searchers and pursuers, too?

The first step in realizing a nation of 350 million learners, then, may be to first see a nation that is striving to learn. Imagine every major American institution resolving as its mission to meet the full-stack learning needs of new constituencies of learners, undergirded by the humanities? Or the body corporate mainstreaming learning leaves and credits for employees? What if, in addition to AI literacy, governments, corporations, foundations and universities dwelled on a more foundational measure of an active lifelong learning literacy?

After all, to commit to a life of full-stack learning, and to be seen as such, not only echoes the learning logic that powers AI - its pretraining phase, that is - but is also the most durable way to assure one’s ability to keep up with technology trend lines, no matter when they emerge and where they extend.

In late 2022, weeks after settling in Blacksburg, I found myself at the River North Correctional Center, a Level IV prison in far Southwestern Virginia, near the North Carolina border, in a town called Independence. There, alongside Dr. Johnson, I observed a seminar he led centered on Zora Neale Hurston’s 1937 novel Their Eyes Were Watching God. I watched a group of inmates - many incarcerated for decades for violent crimes - wrestle with questions of self-discovery and independence, love and relationship, race and gender, nature and fate.

Looking back at my notepad from that day, one scribble stands out:

“Somehow, I’m envious…”

Removed from our what-have-you-done-for-me-lately, hall-of-mirrors culture, these fellow human beings were - before my eyes - awakening an innate spirit of learning for learning’s sake, and I could see the light, and windows, it offered them, even in their circumstance of resignation. It was a kind of alchemy.

“What if our culture ‘out there’ featured people young and old grounded not merely in today’s know-how, but a spirit of how and knowing for all time?” I wondered.

As I learned there and in my subsequent work at Virginia Tech, deep down, learners in our AI-ascendant era crave belonging, being seen and braving new worlds of knowledge just as much as - and maybe even more than - credentials and their immediate marketability.

Burns is indeed right and our Founding Fathers were prescient: in our AI-enables-everything landscape, in which opportunities to activate one’s sense of purpose have never been more proximate, and the need to keep up with what’s new feels more pressing than ever, committing to a lifelong pursuit of learning for learning’s sake, of things changing and unchanging, and to seeing the learner in all Americans, may be the highest “responsibility of citizenship” - and the happiest pursuit of all.

“We have to look in the mirror,” said U.S. Senator Chuck Schumer in the aftermath of the November 2024 presidential election. He, of course, was not alone in calling for a period of introspection in the Democratic Party.

“Introspection,” and its word cousins - from “self-reflect” to “soul search” - have been coursing through left-leaning discourse these last months.

But what exactly does it mean to “introspect”?

“A reflective looking inward: an examination of one’s own thoughts and feelings,” according to Mirriam Webster.

But is what’s most pressing at the moment the need for Democrats to reflect… on their own inner monologue?

To some extent, yes: for nearly a decade, liberals have embraced a sometimes-strident posture centered on the primacy of identity, righteousness of their cause and uncritical fanfare for its leaders - a posture many voters found uninspiring, and even unbecoming, in part given American liberalism’s inspired heritage as a center of inclusion, invitation and intellectual dynamism. I was once a part of this uninviting posture.

But the aftermath of the 2024 election may demand more than introspection; indeed, on the eve of both President-elect Trump’s inauguration and a leadership election within the Democratic Party, it may be time for a commitment to extrospection: a time to consider and observe, with depth of feeling, what is wholly external to, and even far-flung from, the self.

But, you might say, what utility, really, is there to be found in this semantic switch from “introspection” to “extrospection”?

“When we say introspect, we actually mean extrospect!,” I can hear from many-a progressive.

Language is all we have, though. Words create the culture - and the realities - we live into. Precision… it still matters.

Reflect on our uniquely-American language, for a moment: words and phrases like “start-up,” “influencer,” “innovate,” “hustle,” “entrepreneurship,” “American Dream,” “Red State, Blue State” and “What do you do?” have created just some of the realities so many of us behave and believe into.

And as it happens, according to many voters, it was issues having to do with language - or, more precisely, the ability to exteriorize one’s interior language in the form of free speech - that were at least partially determinant in this election.

Language really, is, all around.

And now, enter into the discourse as a main character of sorts: “Introspect.”

To commit oneself, and a political party, to an introspective project is akin to Monday-morning quarterbacking one’s own play calling in last night’s game.

Listening to any number of early reflections from those most active in the Democratic Party’s story of 2024 - from Harris campaign officials on Pod Save America to former President Obama’s remarks at a Foundation event in December - it’s hard not to be struck by the self-seeking nature of the discourse to date.

‘We just didn’t have enough time.’

‘We don’t have an equivalent digital media ecosystem.’

‘We were victims of anti-incumbent conditions sweeping the globe.’

In fact, transcripts of too many discussions in left-leaning media these last months read like a parade of “I’s” and “We’s” … with scant language devoted to respectful, reverential - and even emotive - reflections about the tens of millions of fellow Americans who quietly disagreed. Is there no wisdom to be gained from them?

Sure, it’s early days, but bad habits settle quickly, and cascade down from the top.

What if more electoral postmortems had included remarks along the lines of:

‘If only we’d better understood how tens of millions of our fellow Americans felt.’

‘The other side wasn’t just savvy… they saw wisdom, not merely wants, in the grassroots.’

‘Before creating our own podcast ecosystem, maybe we should become listeners of theirs?’

To extrospect would be to travel to your opponent’s sideline and listen … to not merely point from midfield, but to go all the way and listen - without judgment or snark - again and again, to the pods they believe are saving America.

To extrospect would be to sit with dyed-in-the-wool conservatism - including the debates and divisions therein across a movement as old as the nation - and stay seated. And even find an idea or two that inspires.

To extrospect would be to revere parts of the American past previously and wholly disregarded as shameful and find a pearl of wisdom in people previously torn down.

To extrospect would be to see beauty - and not off-putting bravado - in tens of millions of middle-class Americans who say they believe they voted for security, sustenance - and to feel seen.

To extrospect would be to see profound civic faith, not irresponsible judgment, in those who believe, like William Buckley Jr did, that ordinary Americans - randomly selected from a phone book - might be just as capable at leading our government as those from credentialed corners and coasts.

To extrospect would be for me to hear a fellow American tell me, the son of immigrants, “Rishi, the loss of jobs in our community the last sixty years correlates almost perfectly with immigration policies that led to your family’s arrival in this country” and say simply, “There’s deep truth in your reflection, and I understand.”

In short, to extrospect would be to listen from windows… before reflecting in mirrors.

When we courageously extrospect - that is, when we sit with, take great pains to see, lift up and even feel inspiration from human others, and their best ideas - we ultimately enrich ourselves. Slowly, we improve our own posture, our own positions and our own purpose - and win.

Before the election, I published a public essay chronicling my drifts this last decade from today’s Democratic Party, notwithstanding having been an early fundraiser for Kamala Harris, an Obama-movement social entrepreneur and leader of many-a-liberal-leaning institution.

Truth be told, I thought of my process and the piece, entitled “The Wonder Years” - in which I wondered if there was still room to fearlesssly wonder inside today’s Democratic Party - as an introspection of sorts.

But, in retrospect (yes, another ’spect), what undergirded my own journey of introspection - indeed, what came before it, a prequel of sorts - was a long phase of extrospection after 2016’s surprising electoral result. An extrospection that consisted of reading books by unfamiliar conservative writers while others asked why. Of quietly listening to right-leaning podcasts while running by. Of traveling through YouTube’s memory lane and finding old episodes of Firing Line. All while reserving judgment, and the temptation to center myself in the story.

Over time, it dawned on me: has the fact of conservatives coming of age in an America dominated by left-leaning hegemonic institutions - in academia, the media and mass culture - been a blessing, and not a curse? A blessing in that it’s gifted them with an ability - and even a superpower - to sit constantly with the ideas of political others?

Indeed, up until November 5, 2024, was to be a conservative in America a fundamentally extrospective exercise?

Does swimming hard against the currents of mass culture activate the muscles of extrospection? Whereas does swimming with ease with these same cultural currents cause these same muscles to atrophy?

While there are bright extrospective spots to be found on the left and right - including Cornel West and Robert George whose new book Truth Matters dwells on these themes - much work lies ahead to advance an American political culture that prioritizes curiosity before conviction.

But as we approach our 250th anniversary as a nation and as I, like many, reflect on what’s empirically proven astonishing about the American experiment, isn’t it… our spirit of extrospection?

The basis of entrepreneurship, of self-government under God and of our aspired-for perfect union is the superpower of extrospection: of channeling our shared inner expat - after all, we’re all descended from expats of sorts - and watching human nature with an eye on wisdom and not wisecracks… and meeting it where it is: with public institutions that check our worst impulses, with products that speak to our needs and with a patriotic purpose that helps us answer, “Why?”

Martin Luther King Jr., whose 96th birthday we observe tomorrow, once said:

“Rarely do we find men [people] who willingly engage in hard, solid thinking. There is almost a universal quest for easy answers. Nothing pains some people more than having to think.”

Might committing this year to extrospection - a quest to live outside ourselves - form the starting point of the hard, solid thinking Dr. King dreamed of?

He was right. It made no rational sense; indeed, a simple pros versus cons spreadsheet would have talked some sense into me. After all, I was now married - and we had a baby on the way! Stability mattered.

“Stay, Rishi.”

I was “somebody” at Google, too: my first job at the company in early ’06 had been to serve as a speechwriter for then-Chairman and CEO Eric Schmidt.

But six months earlier, I’d been swept away and there was no turning back: swept away by the election and inauguration of Barack Obama and the prospect of participating in bottoms-up change in an era with a leader who understood the power of social entrepreneurship, and the changemaker in all of us. 

I did leave Google. And my wife and I moved to Detroit, where she’s from, in 2010 to found Michigan Corps, an online civic action platform inspired by President John F. Kennedy’s founding of the Peace Corps in Ann Arbor exactly fifty years earlier. “Ask what you can do for your state,” we said. Within a couple of years, we were featured in The New York Times, interviewed on MSNBC, partnered with the Obama White House, and the State of Michigan, and appeared at the Clinton Global Initiative - standing with former President Clinton, to launch a first-in-the-nation Detroit-based microlending initiative, one which later expanded to Flint - to celebrate our growing model of grassroots civic engagement. Happily, we felt like little ripples in the wider Obama wave.

Years later, in the mid-2010s, after a stint helping expand Twitter across Asia Pacific, then-lame-duck President Obama inspired me again: after years as an expat, my family and I moved to Chicago in part to reconnect with the Obama movement, where the former President’s emergent Foundation was being built amidst a community which - above all else, it still seemed to me - emphasized the power, and wisdom, of the grassroots over the grasstops. “Yes, we can.”

I proudly attended, standing alone in the back of a cavernous hall just miles from Chicago’s Grant Park, the President’s farewell address on January 10, 2017. It felt like a pilgrimage to pay homage, not just another jam to share on Instagram. Months later, I was invited to and attended the first Obama Foundation Summit and reconnected with fellow social-change-y friends from the prior decade. At the end of 2017, I even joined President Obama’s town hall in New Delhi. Fan boy, much?

In short, as recently as a decade after his first election as President, I remained swept away: I was ecstatic to help shape, but mostly to have been shaped by, the Obama era and its inspired community. I still am.

But looking back at the end of my decade of immersion in all-things Obama, I was also beginning - quietly and in my interior life, mostly - to ask hard questions in light of the political upheavals, and illuminations, of 2016. I assumed we all were. And to me, my quiet introspection didn’t feel edgy in the least - after all, I had for years been drawn to the former President precisely because of his deeply introspective spirit.

Looking back on November 2016, what had he missed, I asked myself? What had I missed? Before harshly assessing other Americans, how might I self-assess - and grow?

And, yes, could this fired-up, ready-to-go movement - in a newly-divided America - revisit what first gave it flight in then-Senator Obama’s July 2004 Boston convention speech: namely, a contemplative, conversational, conscientious kind of progressivism that resisted the temptation to Other … others? “E Pluribus Unum,” President Obama would say. “Out of many, one.”

More than three years before leaving Google to found Michigan Corps in 2010 - while I was still at the start of my stint in Silicon Valley - I found myself one spring evening at San Francisco’s Club Fugazi, helping host a fundraiser for the city’s then-little-known District Attorney: Kamala Harris. 

To be sure, I wasn’t “somebody” - or even a “kinda somebody” - on her campaign but, in 2007, I served on Harris’s Finance Committee, helped organize a couple of events, shared ideas regarding opportunities to upgrade her digital presence, occupied friends’ inboxes with calls to donate to a rising political star and got to learn from key players in California Democratic politics, many of whom have risen significantly in national prominence since, including U.S. Representative Ro Khanna. Whether or not I was memorable, they certainly made an impression on me.

Looking back at that year, I recall, yes, being drawn to Harris’s story - after all, my mother, like hers, was born in the Indian city of Madras. But I mostly recall feeling pulled by the social currency that came from being on her team, and not by big ideas per se. 

For 24-year-old Rishi, that, then, was just fine: social media hadn’t yet taken off but e-mailing fellow 20-something friends en masse, in ’07, to RSVP at kamalaharris.com for events at swanky San Francisco lounges had its own cachet, too. 

For years, family and friends have said to me, “Rishi, you’re the one that first introduced us to Kamala Harris.”

And sure, it was nice. To have felt like a first mover - then, and for the decade that followed as she rose to the U.S. Senate - and someone who, in my very little neck of the woods, could claim even just some of her pixie dust. 

But at the same time, a decade after first volunteering for her, I’d begun to wonder, quietly and on the inside: politics is about more than my feeling of self-worth, right?

Throughout much of my career, which has included stints as an entrepreneur, executive and educator, I’ve found myself happily in the midst of some of our nation’s most prominent Democratic figures.

A photograph of a beaming Franklin Roosevelt adorned my dorm room wall at Princeton. Shaking President Bill Clinton’s hand after a speech he delivered in 2000 celebrating the Progressive Era of the early 1900s was and still is a high point. The precious real estate alongside my college yearbook photo pays homage, in part, to Robert F. Kennedy. Serving as a Princeton University Trustee alongside former U.S. Senator Paul Sarbanes, and current Supreme Court Justice Sonia Sotomayor, furthered my reform-minded orientation. Ralph Nader’s Project 55 is how I found my footing in public interest work. I recall the knot in my stomach the night Senator John Kerry lost the 2004 presidential election, a campaign I phone banked for. 

In 2009, I was enthused to help contribute to a Center for American Progress white paper recommending a more active role for the U.S. Department of Education in providing more postsecondary data to high schools. When Andrew Yang told stories from the heartland in his 2020 race for the Democratic nomination, and proposed Universal Basic Income, I was proud, on behalf of the Knight Foundation, to have helped him and his organization, Venture for America, get to know Detroit in 2011. Following cues in the culture I found myself in, I concurred with friends and family in deriding Republican candidates, including Governor Mitt Romney, as “disconnected and dangerous” throughout the 2012 election cycle. 

Saying hello to Caroline Kennedy after a 2017 Obama Summit dinner to tell her that her father changed my life is a moment I’ll tell my grandchildren about. That evening, Pete Buttigieg, then the little-known Mayor of South Bend, Indiana, was sitting across the table from me at dinner and we exchanged brief words about Michigan Corps after our group’s icebreakers and pleasantries had concluded. We follow each other on Twitter. And when entrepreneur Jason Palmer challenged President Biden in the strangely-muted 2024 Democratic primaries, and defeated him in American Samoa, I was proud to call Jason a friend thanks in part due to our prior shared service on the board of Village Capital. 

I could go on.

But if collecting affiliations and experiences many identify with the American left were a goal, I could pass the test: a native New Yorker who went to public schools in Queens and then the city’s Connecticut suburbs; a vegetarian son of immigrants who’s still never been around a gun; the recipient of a liberal arts degree from the Ivy League; the occupant of many-a-front-row-seat in Silicon Valley; the co-founder or co-creator of several non-profit organizations, including one focused on black male empowerment, in cities like Detroit; a leader of philanthropic work for America’s largest journalism-focused foundation; a former trustee of my alma mater, and a current director of state agencies and national humanities institutions; and, most recently, a faculty member at an inspired public university where I founded a first-in-the-nation effort to grow the relevance of the humanities - yes, the academic humanities - in preparing reflective leaders and stewards for this AI-ascendant era.

Time and time again, the Democratic Party has shaped my sensibilities; I am who I am because of the oldest active political party in the world. If climbing its movement’s ranks were an outright goal, I’d be able to open my own doors in a community that long felt like home.

But today, and in recent years, I’ve found myself politically adrift.

After all the inspiration I’ve felt, perspiration I’ve committed and currency I’ve earned in and around progressive communities, I confess - on the eve of this presidential election - to having drifted away from today’s Democratic Party.

Why?

For years, I’ve struggled to confront this question, openly and socially, let alone attempt to fashion an answer. 

Like many, my best thinking on all manner of life’s most vexing questions sharpens the more I think out loud, traverse with and test my ideas; but outside of those closest to me, the charged, righteous atmosphere of the last decade has presented such few opportunities for wide, candid, learned discourse. How thick is my skin, I’ve wondered, and is politics-by-therapist a thing yet?

I’ve agonized for months: might a longer-form, admittedly-vulnerable written attempt to publicly advance a long-suppressed interior conversation to a wider exterior, however belated, prove cathartic - and constitute the kind of citizenship worthy of the civic-engagement values I’ve long professed to hold dear?

And in our quick-answer, quick-judgment culture - one I’ve perpetuated myself via leadership roles at companies like Twitter - what if the reflections I share from my inner life consist not of the rushed pronouncements we’re all inundated by but instead with… more questions?

Perhaps a helpful place to start is with the words of an architect of one of the Democratic Party’s great institutional legacies: the late Eli Segal, a former aide to President Bill Clinton and the founding leader of the Corporation for National and Community Service, which oversees our nation’s preeminent national service program, AmeriCorps. His national service vision, like that of President Kennedy decades earlier, inspired my own service journey.

One late afternoon in early ’05, my co-workers from College Summit and I gathered in a dimly-lit conference room at the Watergate (the office building, not the infamous hotel) to hear Segal speak to us about the inspiration and perspiration it takes to make lasting change. College Summit, now PeerForward, is itself a special organization where I have crossed paths with - and been inspired by - many who have gone on to build prominent careers in Democratic politics, including Jaime Harrison, PeerForward’s former COO and current Chairman of the Democratic National Committee.

Segal said something that afternoon many of us will never forget: 

“The greatest movements are those in which poetry and prose are in stride with one another.”

Heads nodded not just because he seemed right in the abstract, but because Segal’s instincts seemed to be affirmed by our most recent lived and learned experiences.

Yes, maybe it was because we were young, but it did seem self-evident to many of us in the room - in the midst of a turbulent George W. Bush presidency - that for most of the prior century the Democrats were the party of not just inspired chords but intellectual coherence, and curiosity. The party of Roosevelt, the Kennedys and Clinton was soulful - and smart. The two impulses balanced each other; to immerse oneself in Democratic politics was to feel your soul soar, and your curiosity deepen. Right? To be progressive was, almost definitionally, to exude an always-on, cosmopolitan openness to new inspiration and ideas… to be the opposite of stiff.

And Segal, in my mind at least, wasn’t just referring to the importance of “well-run” movements. I took his passing insight as an allusion to the criticality of mixing political purpose with precision, personality with principles and, yes, poetry with prose. A politician’s platitudes might primarily be designed to evoke base emotions, yes, but any tendencies to wax exclusively poetic on the Democratic side was balanced by an always-on cerebral culture, too, one that also invited in and insisted on the wisdom of all Americans, it seemed to me. 

Roosevelt’s “This generation of Americans has a rendezvous with destiny…” and the all-hands-on-deck New Deal. Kennedy’s “Ask what you can do” and the rallying cry of the Peace Corps. Clinton’s “We know there's not a program for every problem,” and the beginnings of AmeriCorps.

Agree or disagree on their particular areas of policy emphasis, the Democrats, I thought, understood the power of political poetry in shaping American self-understanding and identity, yes - but, above all else, they engaged audaciously with the prose behind big American ideas, no matter their point of origin.

And then came Barack Obama. 

Wasn’t his singular mix of poetry and prose why we fell for him? 

“The President fills the room with charisma, yes, but also with a sense that he’s the smartest person in the room,” a friend of mine who worked in the early Obama White House once told me. 

Watching, for instance, the former President interrogate the minutiae of health care policy, in bipartisan town hall after town hall, summit after summit in 2009 and 2010, showcased a Democratic Party culture long built around an endearing embrace of the vitality of ideas - and idea exchange - no matter the message or the messenger. 

“I welcome your ideas,” Obama would often say to political opponents. In a nation founded on a sacred idea, that was part of what was captivating. 

Beginning 2004, an inspired national conversation we could all be proud of - one grounded in ideas - was itself his central theory of change.

What happened?

If President Obama was heir not just to a party trajectory undergirded by inspiration but to a governing tradition that saw the intellect in everyone, why in the last ten years has it begun to seem to me that the Democratic Party has stopped ascending towards a poetry and prose worthy of posterity - and instead begun descending to a poetry linked almost exclusively to identity and a prose fast losing its spirit of inquiry? 

“What’s the best argument against your position?” I try to say as often as I can at our family’s dinner table. “Not just any argument… but the best argument.”

On any number of issues gusting through our nation’s public conversation, the answers aren’t always neat, and no one actor - public or private, individual or institutional - has a monopoly on the right answer. On this much we should be able to agree, right?

Isn’t it, then, essential to ensure our civic tables are chock full of unusual suspects with seating arrangements that spur debate and leaders who open with a poetry that transcends any one tribe and close with a prose that anchors in truths that have withstood strenuous debate? To do so is to lead with a humility grounded in engagement, and not a hubris grounded in expertise; this, it seems to me, is how Democrats led until a decade ago.

In the quiet of my inner life, and on account of perceived vacuums in Democratic leadership, my poetry and prose began to wander. I started to wonder. 

I’ve wondered… not to pass judgment, nor because I have clear policy preferences here, but only to channel the sincere inquiry in my heart. It’s the intrinsic value of inquiry - in and of itself - that the Democratic Party taught me to pursue, above all else.

On social change, I’ve wondered, why have Democrats begun to present as having a monopoly on the intention to make the world a better place? Republicans and independents don’t wake up in the morning seeking to realize a world in which Americans, their allies and marginalized people around the world are worse off and less able to realize their respective dreams, do they?

On speech, I’ve wondered, what should I make of a party that is an heir to civic warmth and wisdom, yes, but also one that has passed scornful judgment on conservative political opponents for decades? Bush, Cheney, McCain, Romney, Ryan, Trump, Pence, Vance - all of these leaders, and more, including many-a-Supreme-Court-appointee, have, at one time or another, assumed the role of polite society’s “disconnected and dangerous villain.” Regrettably, I used to partake in the snark myself.

On race, I’ve wondered, what might Dr. Martin Luther King Jr. make of a Democratic Party whose leaders, past and present, have begun to speak so explicitly - more each passing year, it seems - of voting and governing in terms of race, even as opposing movements grow more racially eclectic?

On affirmative action, I’ve wondered, in an increasingly multi-racial America, aren’t the poorest among us most likely to bring life experiences worthy of the most inclusion? 

On social mobility, I’ve wondered, why has the percentage of American children raised without their fathers climbed from 9% to 25% since the launch of President Lyndon Johnson’s Great Society federal welfare programs?

On immigration, I’ve wondered, what should I make of the fact that the decline of American working-class wages correlates and tracks, strikingly, with the concurrent growth of our nation’s immigrant population after President Johnson’s Immigration and Nationality Act of 1965? What does it mean that this Act, which was the subject of my college senior thesis, is essential to my self-understanding? Without it, my family would not have been able to immigrate to the United States.

On education, I’ve wondered, what should I make of the fact that American educational outcomes, as of President Obama’s second term in office and relative to the rest of the world, have, some argue, declined since the establishment of the U.S. Department of Education in 1979?

On abortion, I’ve wondered, that visceral, protective feeling of fatherhood that took hold inside of me the moment I knew we were pregnant with my daughter, weeks before even first hearing her heartbeat, and eight months before she was born… was that feeling of life invalid? Is there any room to acknowledge this feeling - merely the feeling itself, and just sit with it - in Democratic circles?

On health, I’ve wondered, why have Democrats been so quick to wholly caricature Robert F. Kennedy Jr., a man - as complex as ever, like all of us - who has devoted much of his life to challenging America’s cozy industrial complexes and ensuring America’s children come of age toxin free and mentally well?

On covid, I’ve wondered, even as a triple-vaccinated Obama voter, was all the hate directed at those who dared ask questions about virus origins and ordinances worth it?

On wealth, I’ve wondered, what should I make of the fact that America’s wealthiest counties now vote for Democrats by a wide majority? Is this a fact that should give me pause - or galvanize my sense of possibility - about the progressive movement?

On the Supreme Court, I’ve wondered, why is there such dissonance between the Democratic Party’s caricature of conservative justices as “evil” and the observed behavior of these justices once on the Court? On readily-available audio of the Court’s oral arguments, which I listen to as often as I can, I don’t hear evil but, rather, women and men engaged in reasoned, respectful debate with an eye - on issue after issue - of trusting in the wisdom of the American people, and not the whims of nine justices who happen to occupy the bench. No matter how I may feel about them personally, reasonable people could plausibly argue that their legal theory ought to be democratically empowering, and not endangering, couldn’t they? And, regardless, how could a court occupied with the allegedly ever-present danger of Bush-and-Trump appointees reach unanimous 9-0 consensus in nearly a majority of the cases it handles, including many outcomes favorable to progressives?

On politics, I’ve wondered, isn’t a long-term achilles heel for Democrats the rise of a political movement which self-identifies as conservative at a federal level - insofar as it is skeptical of the concentration of distant power - but embraces more progressive approaches to governance the more proximate power is located to the people? After all - notwithstanding our nationalized, digital era - don’t our place-based lives remain primary and shouldn’t localism, in the de Tocqueville sense, remain paramount - and, indeed, central to our uniquely-American signature?

On democracy, I’ve wondered, isn’t the fact we do not live in an outright democracy - but instead, to be more precise, as citizens of an enduring federal republic, one whose aim is in fact to guard us against unpredictable majoritarian impulses and check unhinged power at each step - what we ought to be celebrating as we approach our 250th anniversary as a nation?

On the presidency, I’ve wondered, considering the constitutional limitations on the chief executive, and the aforementioned fact of our inhabiting a republic, why have we all begun to view the presidency in unnecessarily monarchical terms? What, if anything, does the left’s perpetual state of emergency around the prospects of Republican presidents reveal about their deeper sensibilities relating to… power?

Again on the presidency, I wondered, particularly while immersed in Detroit’s philanthropic community as an entrepreneur in the early Obama years, is “federal dollars in, transformation out” the most essential way to view how people and places realize their potential? If progress were so straightforward, might administration by AI be imminent? Or might something more foundational - and human - be at play in the circuitous journey of communities, and a country? Why have Democrats at a federal level begun to sound more like the foundation presidents and venture capitalists I come across professionally - e.g. “we’ll invest in this and that” - and not stewards of a continental-scale republic enabling, rather than presupposing, investments made by those at other levels of government?

On policy, I’ve wondered, as I devour liberal-leaning podcasts and prose, why does it seem to me that - in the main, after the anti-Republican snark - one way to summarize the Democratic policy posture is too often simply the underwhelming notion of… “more”? What are “end points” at which Democrats believe its investments in this or that, or focus on enabling a particular policy outcome, must necessarily stop? Or are there no end points? Is this less-interesting notion of “more” - which presents less storytelling tension than the right’s emphasis on limited power - a partial explainer for the lack of a sticky, long-tail, large-scale digital media ecology built by and for the left? And by anchoring its movement in always-elusive issue-by-issue end points, have Democrats unbeknownst to themselves ceded, at a federal level at least, the ground on first-principled “starting points” to Republicans? One way to explain the success of Ezra Klein, I think, is his center-left-but-still-curious-listener orientation to exploring this sort of policy prose, which lies well beneath the political poetry.

On progressivism, I’ve wondered, what happened to the wear-it-on-your-sleeves, skeptical-of-corporate-power, peace-at-all-costs progressivism of Robert F. Kennedy, Howard Dean and, yes, Bernie Sanders?

On walking the progressive talk, I’ve wondered, why does Jimmy Carter’s post-presidency - humble, heartfelt and Habitat-for-Humanity-committed - move me more and more with each passing year, especially when contrasted with the post-presidencies of other “progressive” Presidents? 

On the conservative sensibility writ large, which was the subject George Will’s book of the same name, I’ve wondered, isn’t the defensive, chip-on-shoulder sensibility observable among some conservatives - which, to liberals, can come across as unkind - understandable given so many on the right came of age in a culture powered by the left?

And on courage, I’ve wondered, why don’t we experience, in our center-left media environment, more daring critiques from within - structural critiques, not at the edges - of the Obama and Biden years? If uncritical fanfare for a movement’s leader is the existential threat facing our nation on the other side, as liberals allege, might Democrats find a way to more explicitly be the self-critical change the party seeks in the world?

I’ve wondered about these issues and many more, thanks in no small measure to the critical-thinking spirit of the Democrats I came of age admiring. Had I come of age as a Republican, with a decades-long stake in the party, I’d undoubtedly be reflecting on the coherence and consequences of its movement’s journey.

Most of all, though, I’ve wondered, is there still room to fearlessly wonder inside today’s Democratic Party? 

“Mr. Mayor, I wonder, what might a citizenship strategy for the city entail?” I asked rhetorically in a meeting with Detroit Mayor Dave Bing in 2012. 

I was trying to illuminate a larger point inspired, in part, by the early Obama years: what if governments across our nation saw it as their duty not merely to problem solve, from above, on each and every issue they confront but to also see each and every citizen across political parties with civic wonder - and, indeed, as a vessel of civic wisdom - whose ideas might be channeled to serve big civic outcomes. 

What if we grew the civic table, to include new waves of citizens, and ensured the doors stayed open? It’s this attitude - the Obama poetry of “Yes we can” and the Obama prose of “I welcome your ideas” - that undergirded the work of Knight Foundation, the BMe Community of black men and all else I was honored to help lead in Detroit, including founding Michigan Corps. In my mind, Detroit’s rebound, in recent years, is in no small measure due to its community’s open-source, “everybody-in” attitude in the years immediately following the Great Recession.

This was the hallmark contagious spirit of the early-Obama years, which harkened back to the best of 20th-century Democrats: a feeling that governments, politicians, 501(c)(3)s, foundations, think tanks and other organized instruments of the establishment did not have have a monopoly on good ideas - and that there was untapped, and sometimes disruptive, civic wisdom to be harnessed from the crowd, wisdom that then ought to find its way back into public institutions at all levels. James Surowiecki’s 2004 book, The Wisdom of Crowds, captures some of this essence, too, reminding us that, often, the wisdom of many transcends that of an elite few.

And if “wisdom comes from wonder,” as Socrates said, perhaps the most pressing question to ask then is: what happened, in less than a generation, to the party’s fearless, anything-goes spirit of wonder… a spirit that used to live collectively and in the open. How did open source become closed circuit?

One answer begins, I think, in April of 2001.

That month and year, I recall sitting in the recently-opened Frist Campus Center at Princeton University, where I was a freshman, reading a viral essay being passed around campus: ”The Organization Kid” by David Brooks, now a columnist for The New York Times. Today, I might encourage Brooks to explore writing a sequel: “The Organization Adult.” 

In his essay from ’01, with my alma mater serving as a case-in-point backdrop, Brooks described a generation of future Gen-X and millennial American leaders who had then, while in college, developed a peculiar propensity to trust in authority, please others and orient towards productivity, above all else. While maybe not striking in a vacuum, these tendencies were noteworthy, Brooks argued, when compared to the higher education experiences of prior generations that indexed more heavily on spirits of irreverence and intellectual curiosity. Where had all the authenticity gone?

I felt, rather uncomfortably, that the article described me to a tee. My ambitions, however boldly I cast them then, were fundamentally organizational and institutional in nature: that is, they amounted to dreams of climbing ranks, minimizing contention and, naturally, living life in 30-or- 60-minute increments of productivity. Such was already the life of this older millennial; I finished reading Brooks’ article and, at the heavy, haughty age of 18, moved on to my next “appointment.” Ha.

In fact, such was our state of affairs, that I recall working with classmates to organize an “Intellectual Week” on our campus in 2003 or thereabouts - a daring call to action for otherwise pre-professional undergraduates to, gulp, invite professors to lunch, engage in spirited debate and change the topic from whether we’re headed out that night or not. In retrospect, I cringe, yes, but smile, too; after all, it was college.

But, today, I wonder: are we all now Organization Adults? 

All political movements share sensibilities, of course, but I wonder if the shared sensibility that has descended upon the Democratic Party’s coalition in the last decade or so has also ushered in a peculiar kind of speech culture, one that’s “CP” (not “PC”). A Crowd-Pleasing, self-censoring, Organization-Kid persona that predated, presaged and then was pushed ahead by the performative era of social media, all of which coalesced during the later Obama years. I’ve been a part of it, to be sure, but now I wonder, can the groupthink of crowd pleasing be country leading?

Democrats respond, it seems, that the emergency that is President Trump warrants a kind of talking-point unity anchored, primarily, in identity, and not in ideas - the identity of the former President himself, first and foremost, and then that of key liberal constituencies under siege by him. 

I reflect back, including from personal experience, and think: haven’t 21st-century liberals lived in a perpetually-alarmist state against any-and-all Republicans? And at some point, isn’t engaging with the most compelling messages of an opponent’s movement, and not merely its least compelling messengers, how movements break out of adolescence and into adulthood? Isn’t this the party’s inspired inheritance?

Disengaging from the most wondrous debates of the day and conforming, as some of us Organization Kids did a generation ago, has likely, in part, led to what The Economist reported two weeks ago as the “Trumpification” of American policy: that is to say, while Democrats were resisting and engaging on matters of identity, the contours of our nation’s debates - the big ideas themselves - on issues from immigration and trade to peace and growth are now arguably largely confined to policy spectrums first proposed by President Trump and the Republican Party.

It’s this, the party’s culture in and around speech, that has me adrift more than anything else. And, admittedly, my sense that democracy - let alone the best political ideas - empties and hollows without freedom of thought, inquiry and speech.

What if the winners of the future are those who lead communities of people who are devoted to channeling their originality, the permission to go off script - and ponder? 

As a former leader of Silicon Valley companies and causes, I had many-an-occasion to be awed firsthand by the long tail that is the passion economy unleashed by the Internet. But I also experienced what the debates in and around free speech look like abroad - and have encountered, on my own personal devices, what it feels like to have speech blocked, and platforms censored. As an American, it’s a deep, sinking feeling of loss.

I’ve also had occasion to visit correctional facilities, meet with incarcerated members of our society and observe firsthand what happens to the human spirit when access to speech is stifled - and then when it’s set free.

How many of those who advocate for the tightening of our national conversation, given the alleged exigencies Republicans present, have experienced the spirit-breaking feeling of losing access to one’s ability to freely express or access to the voices of one’s fellow citizens? What happened to the profundity of seeing latent wisdom in one’s neighbor - ”asset-framing,” as Trabian Shorters, the inspired founder of BMe, calls it - and Justice Brandeis’s doctrine that the answer to inconvenient speech “is more speech”? Have the liberal become… illiberal?

And then, I wonder… can a party atrophying its muscles of confronting compelling opposing ideas long survive, let alone a party over-rotated to assailing an opposing movement’s messengers?

Two-and-a-half years ago, in March 2022, as I was getting to know Virginia Tech, where I’m currently privileged to serve, I attended an event one evening in our Blacksburg campus’s Squires Student Center.

Prominent progressive Cornel West, now an independent candidate for president, who previously challenged President Biden in the 2024 primaries, and prominent conservative Robert George spoke together at a forum entitled: “I See You.” 

Moderated in conversation by Dr. Sylvester Johnson, a leading scholar of African American religion, West and George spoke for more than an hour not merely about disagreeing without being disagreeable, but about something deeper: about feeling fondness, and even love, for one another… not in spite of their differences, but because of them. 

“I see you.” 

I keep the flier of that evening’s event on my office’s wall.

Here at Virginia Tech, where our motto is “That I May Serve,” I felt called the following year to develop a program that draws on the humanities to usher in a world in which a culture of fully - and substantively - seeing others isn’t merely regarded as a cutesy ripple, but a critical requisite for leading civic waves we can be proud of. 

I’m asked often by friends and family: why draw on the humanities? And what are they, anyway?

Fortunately, months before the launch of ChatGPT, I had ready a six-word poem I’d written to help express the antidote - indeed, the North Star - our culture sorely needs:

Awe and wonder,

In the other

Again:

Awe and wonder,

In the other

My pitch? The political-and-professional superpower of our era may lie in and around the humanities, and their capacity to cultivate the other-centric skills and sensibilities of storytelling and story listening, introspection and imagination.  

My dream? An “I-See-You” world in which fearless awe and wonder in the other - past, present and future others - is not merely a fuzzy afterthought, but regarded as the essential building block to growing a kind of human fulfillment that endures.

We live in a culture of mirrors, I often say, self-involved and short-form - a culture undoubtedly now reflected in our politics; how might we usher in a culture of windows, long-form and other-centric?

Looking back on that young, self-involved volunteer for Harris’s 2007 campaign, and the other-oriented change agent empowered later on by the early Obama era, I wonder, in retrospect: were those the tail end of The Wonder Years?

And then, I wonder, what political currents today, however fallible, most embrace the complexity - indeed, the beauty - of Americans who dare to wonder?

What if, in addition to drawing initial inspiration from what the lights draw our attention to, we also resolved to illuminate and find inspiration in what was unlit?

In U2’s 2004 track “City of Blinding Lights,” frontman Bono sings:

Humans, since time immemorial, have long been drawn to bright lights - of stars, of fires, of cities. But also the bright “lights” of conflict, of caricature, of calamity. Sometimes our draw to the light fulfills… often, it does not.

Bono sings about both sides of this coin: “Oh, you look so beautiful” and “the more you see, the less you know.”

But what might it take for U2’s lyric to read more aspirationally? What if it read “the more you see, the more you know?”

There is one path: when we leave our comfort zones to look past the blinding lights - of cities, of countries and of communities of all kinds - we begin to transcend our most superficial senses, and then ultimately serve our deeper senses of understanding and humanity.

India, which celebrated 76 years of independence this week, presents one of the world’s most compelling settings in which to traverse this journey from partial sight of place to total awareness in place.

To visit, live in and observe India is to experience a nation bursting with lights … lights that delight but also lights that can blind. “Sensory overload” is a common refrain from those who’ve just returned from a visit to the Indian subcontinent. But there’s a different type of light at play in places like India as well: that of language.

Bright, shiny language like “the world’s digital hub” and “the world’s largest democracy” to “the world’s youngest, most populous country” and home of “the world’s largest elections” rings true, and undoubtedly elevates our sense of magic around the Indian landscape. Much of this language, and these lights, were on full display during Indian Prime Minister Modi’s visit to Washington D.C. this past June. But settling for and sitting only with these bright lights also dims our view of all else the place might teach and tell us in its details.

During my two stints in the subcontinent as an American expat, I credit the bright lights and language of India with helping create and cultivate in me a lifelong commitment to curiosity, consideration and creativity, all hallmarks of a humanistic sensibility I now seek to make accessible to many more.

Like many expats, while living in Delhi and later in Mumbai, I couldn’t stop asking, reading and expressing. Indeed, it took being overwhelmed by the blinding lights of a foreign subcontinent for me to awaken to a habit I had not fully developed earlier. It wasn’t until living in India, after a humanities education in my home country, that I began to fully grasp the power of an always-on humanistic spirit: that is, to travel more deeply below the surface of the human condition to where the light hasn’t yet reached, and then embrace the personal and professional growth that ensues.

It’s no surprise that my first, earnest attempt at social entrepreneurship - itself an exercise in deeply-felt curiosity, creativity and courage - occurred in India. And I’m far from the only one. It’s why many thoughtful voices, including Walter Russell Mead of the Hudson Institute, are now calling on young Americans to begin traveling to and learning in the unmatched Indian context.

My home country, the United States, bounds with lights and language as well. Our national founding and national aspirations consist of some of the highest-minded lyrical poetry in Western Civilization. “We hold these truths to be self-evident” and “We the people.” 

As Americans, we recalled much of this light last month on the Fourth of July and will again in 2026 as our nation celebrates 250 years of independence. But it’s this very bold language - these bright lights - that have also proved indispensable to and inspired centuries of nation building in service of realizing a more perfect union.

That habit of mind, of seeing the light - but not settling too comfortably in its shine - and then being curious about and caring for the illumination of what remains unlit, is and can remain an individual and national superpower.

And so maybe that’s the superpower of the future: the ability to journey from seeing lights that blind to feeling the warmth - and wisdom - of those that bind… binding nations and binding us to our best selves.

“If I had never dropped out,” Jobs said eighteen years ago this week while reflecting on his decision to drop out of Reed College in Oregon, “I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do. Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backward 10 years later.”

“Again, you can’t connect the dots looking forward; you can only connect them looking backward,” Jobs emphasized. “So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

Wise words that don’t easily leave us.

But how do we build that trust, faith and steel in the midst of our lives, and not just at reflective junctures? How do we intuit that our chosen paths - some short, some long, some connecting personal dots and others connecting professional dots - are indeed in stride with our calling? What is our calling? And as we make decision after decision, how do we assure ourselves that we’re tracking on, and then fully present for, a path sure to fill our hearts down the road?

One answer that Jobs, a polymath who embraced arts and artists, might concur with: the humanities.

While chronicling Jobs’ final product launch event, biographer Walter Isaacson illuminated a North Star at the center of the former Apple CEO’s world view: “Jobs ended, as he had often done, with a slide of a street sign showing the corner of Technology Street and Liberal Arts Street. ‘It’s in Apple’s DNA that technology alone is not enough,’ he said, ‘that it’s technology married with liberal arts, married with the humanities, that yields us the result that makes our heart sing’.”

I’m often asked: “What are the humanities?” In their simplest terms, the humanities constitute the big tent of all human experiences - educational and otherwise - that expose us to the human other: from art and anthropology to philosophy and politics, from literature and linguistics to mythology and music.

But it’s the mind-multiplying, soul-soaring impact the humanities has on us that’s worth sitting with. What kind of impact? T.S. Eliot once said that “genuine poetry can communicate before it’s understood,” so a short poem that aspires to be genuine will do.

“Awe and wonder … in the other,” I often answer when asked about the humanities, always proud of my six-word poem and creative writing debut. Indeed, committing to the humanities triggers the cultivation of a superpower in each of us: a sustained and habitual sense of awe and wonder in human others - and all others - which in turns leads to growing skills and sensibilities of introspection and imagination, storytelling and story listening, listening and leadership.

And, over time, intuition about the world - and oneself - and a kind of soulful stewardship.

These capacities are, of course, hugely universal: indeed, they are as critical for the protagonists connecting the dots looking forward in our technology landscape, like Jobs decades ago, as they are for all of us wrestling with life’s daily dilemmas and delights.

While much of the public inquiry pertaining to the liberal arts, in the United States and elsewhere, centers on the decline of undergraduate humanities majors, in the fall of 2022 I started convening conversations around a separate strand of questions at Virginia Tech, a leading research university whose motto - “Ut Prosim, That I May Serve” - has created a magnanimous culture of giving across the institution:

“In this AI-ascendant era, what’s the superpower of the future?,” I wondered. “If the highest forms of human leadership are consonant with the muscles the humanities awaken, what if we began building an Executive Degree in the Humanities? Imagine a world - and a technology landscape, a political landscape and a cultural landscape - in which we’ve advanced leadership credentials, currency and credibility around humanities sensibilities, and not merely business and technical skills.”

It seemed to me that in a world where computing and commercial skills were increasingly within reach, the leadership superpower of the future, across fields and functions, communities and countries, might just reside with those with a deep sense of their own intuition, compass and light - and an equal depth of feeling for human others near and far. And that this message, while it should be built for all, might be particularly resonant today with those who’ve already lived and led in the complicated real worlds of humans.

As The New Yorker’s March 6, 2023 cover story mentioned in passing, “There are people in their thirties and forties who have been stay-at-home parents, or they work. And they are committed to the humanities.. they have an idea about the value of liberal-arts education.. it’s a matter of life experience. What someone who has been in the grind of life wants to learn more isn’t necessarily linear algebra.”

And so, after twenty years as an entrepreneur and executive in and around technology, I joined with inspired colleagues and advisors at Virginia Tech to launch the Institute for Leadership in Technology, a new, one-year, low-residency fellowship for rising stars in and around our inescapable digital landscape. Drawing on the magic only a structured, shared, serious liberal arts experience can provide, our purpose is to instill heightened skills and sensibilities emanating from the humanities in those who connect the dots, and lead the disruptions, in and around technology.

While the response from people around the world has been heartening since our April 2023 launch, ultimately time will test our own intuition as we ourselves connect the dots of our Institute in real time, building and flying concurrently.

But, at base, can we even connect the dots looking forward? As we climb life’s mountains, can we feel awe and wonderment in between the basecamps, summits and inevitable falls?

Jobs gave us his answer in his commencement remarks, but the example of his life encourages us to look deeper. For it seems that he was, after all, a remarkable example of the sensibilities that accrue and accumulate when drawing on the liberal arts and humanities in life’s page-by-page plot, and not merely at chapter’s end: awe and wonder in the other as a relentless line-by-line, day-by-day, product-by-product habit always in service of higher understanding, beauty and legacy.

Indeed, even Jobs’ last words before passing, according to his sister, channeled this enlightening, lifelong spirit of awe and wonderment, which should recall for all of us what it means to be unabashedly human before the dots have connected:

“Oh wow. Oh wow. Oh wow.”