Ongoing Conversations with Hugh Weber

Photograph of Hugh Weber (2014).

Every thought needs an encounter, a person, an idea, a place, something to inspire us, rattle us, and shake us out of our habitual modes of engaging with the world. For many of us, that encounter was Hugh Weber.

Hugh was a larger-than-life figure who captivated our imagination, made us believe in something more than ourselves, and brought us all together. He still does, as we gather around the breadth of his work, the cornucopia of his connections, and generosity of his legacy.

I can’t believe he’s gone.

Amidst a neutral black sky, Hugh Weber was a bolt of lightning. Seemingly out of nowhere, he appeared in the community, a flash of hope, instantly creating and connecting a thousand disparate nodes, all with an unmistakable voice: one of possibility.

That’s exactly how Hugh lived his life and precisely what he offered the world: a spark, a moment to connect, an opportunity to believe in something beyond ourselves. To believe in ourselves. To believe in our neighbors and cities and, yes, despite our politics, to believe in the elected official right down the street. To not only imagine another world, but to actively participate in its construction, knowing with a sense of empowerment and capability, that anything is possible.

There are three threads that, when woven together, create the fabric of my relationship with Hugh Weber. In many ways, and to speak poetically, he gathered us together in a ubiquitous blanket of imperfection, replete with gaiety, optimism and a shared sense of humanity.

So many of our conversations are still ongoing.

He lived his story alongside us, which, I believe, strengthened his resolve, solidified his vision, and connected us all in a new type of community.

These are the stories of our encounters. In no way do they fully encapsulate Hugh, but yet, may they offer a glimpse into his way of being, his modes of storytelling, and his incredible ability to push us, inspire us, and, at times, madden us. In my estimations, these conversations, when multiplied, demonstrate his power to connect our valences. They remain ever prevalent in my thoughts today.

Firstly, I can’t tell you exactly how Hugh and I met or how many conversations we had over the years, but I can share a few of my favorite memories. Our exchanges were like fireworks. Oh, how he’d jostle me with his references and ideas, his sense of justice and possibility, sending me down rabbit holes for days.

I’m nearly certain that one of our first exchanges involved the hero’s journey of Joseph Campbell. It was a favorite. Hugh was smitten by the story arc, impassioned by a template to view the world. In many ways, the monomyth serves as the personification of Hugh himself: a small town kid, from Milbank, South Dakota, ventures out into the larger world, Philadelphia and Washington, D.C., only later to return a conquering hero of sorts.

Hard lessons make easy stories. Hugh had as many arrows in his back as he had in his quiver. He’d outgrown his own endeavors. Now tasked with imparting his wisdom and sharing those well earned lessons, he searches for a community. In so doing, he learns how to overcome himself, sharing the good tidings of his personal transformations.

It was only natural that our interests quickly turned from the mythology of Campbell to the myth of Orson Welles, from extravagant tales and stories to the embodiment and instigation of a lived life, to a person who epitomized encounters.

Orson Welles created and told fabulous stories. He led an exemplary, wildly out-of-proportion life: nothing extraordinary was ever out of the ordinary. It just was. No one was truly surprised by the accounts that Welles would share or the people he’d met or the places he’d traveled or the adventures he’d embarked upon.

Without question, the same could be said for Hugh.

“I’m going to Qatar next week!” he exclaimed, as he barged into my office one morning.

“Imagine if …” we’d begin our chats. I will miss most of all our conversations.

Imagine if it were possible to recreate the War of the Worlds. Imagine if it were possible to make a film in Hollywood with no previous experience in the cinema. Imagine if we could do all of that today, with those liberties, on that order of magnitude.

We’d smile from ear-to-ear, and Hugh would burst forth with that visceral, belly-clenching laughter. It was infectious.

As a person of inspiration, having led a creative life, Hugh and I incited Orson Welles often, from his outlandish radio broadcast to the insuperable F is for Fake, with seriousness, humor, and a mixture of admiration and exhilaration. Even in his youth, Welles was ages ahead of his time.

The oeuvre of Welles offered us a shared perspective by which to start our own conversations about the world, a lexicon by which to sharpen our views and build our relationship, navigating our exchanges and our ambitions. It also provided a first-hand look inside how Hugh imagined the world: not knowing what’s impossible could suddenly make everything possible.

Contextually, this will help give a sense of his ability to conceptualize the lightness and gravity of a situation, and determine where exactly to add his might.

No story of Hugh Weber could be told without a reference to John F. Kennedy. If Welles offered a lens by which to envision a new sense of possibility, it was JFK who taught Hugh the power of community, and, undoubtedly, the conviction and commitment required to rally around a singular idea, and this is the second thread.

In Hugh’s own words:

“There’s an apocryphal story about President Kennedy visiting Houston in 1962 that has always sparked my imagination,” writes Hugh.

“Kennedy is visiting the city to tour the NASA facilities when he meets a janitor in the halls. ‘What do you do here at NASA?’ Kennedy asks. The janitor earnestly replies, ‘I’m putting a man on the moon.’ ”

I heard Hugh tell this story no less than a dozen times. Each time he told it with renewed fervor, as if he’d just learned it that very day. I’ve told the story myself, just as many times, always with Hugh in mind.

“We choose to go to the moon,” Kennedy continued. “We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win …”

An aspirational idea (and accompanying North Star) to guide us toward a critical mission to come together to accomplish an impossible feat.

Imagine if …

“But if I were to say, my fellow citizens,” continued Kennedy, “that we shall send to the moon, 240,000 miles away from the control station in Houston, a giant rocket more than 300 feet tall, the length of this football field, made of new metal alloys, some of which have not yet been invented, capable of standing heat and stresses several times more than have ever been experienced, fitted together with a precision better than the finest watch, carrying all the equipment needed for propulsion, guidance, control, communications, food and survival, on an untried mission, to an unknown celestial body, and then return it safely to earth, re-entering the atmosphere at speeds of over 25,000 miles per hour, causing heat about half that of the temperature of the sun— almost as hot as it is here today— and do all this, and do it right, and do it first before this decade is out— then we must be bold.”

“Then, we must be bold,” reiterates Hugh. “It’s one of the most dramatic understatements in the history of humankind. It’s also enough to convince a man with a broom that he’s essential for achieving the impossible.”

It’s with this historic reference that, I believe, Hugh’s courage takes shape, and he begins to cultivate and draw the outlines of the type of culture he imagines: a place where inspiration flourishes, community comes together to participate in a shared vision, and people live creative lives.

Yes, it can happen right here. All it takes is an idea.

In this sense, Hugh was a diplomat, negotiating with creatives and communities, sorting connections, organizing ideas to amplify possibility. He’d recruit and nurture talent with confidence, empowering those around him with the craft of a statesman. He’d commission and inspire a broad swathe of the creative class, local, national, and international, and enjoin them to ambitious calls to action.

“I’m working on this new big project,” he’d declare.

The point of it all is not overtly philosophical. As a matter of fact, it’s probably best not to approach the dots, point-by-point, through a philosophical lens, but instead, to follow the lines and connections and see where they lead. After all, when one can become two and two can become three and three can then become something more than itself, inspired Hugh, an entirely new and profoundly flat landscape emerges, one in which presidents and janitors are enmeshed in the same quilt of existence. This is a special kind of place, a community where anything is possible, a place of swarming possibilities.

It goes without saying that these notions— which include diversity, equanimity, and non-hierarchical spaces, popular terms in our modern vernacular— had been inscribed in Hugh’s ethos-in-the-making from the start. They became increasingly more clear over time.

Make no mistake about it. It wasn’t a politics of left or right that interested Hugh. Rather, it was a politics of life, a politics of possibility, of coming together, of gathering around a connection, of inspiring a community of creatives and holding a space, tentatively, for everything simultaneously to breathe.

Ongoing conversations, it could be said, open possibilities.

This space, or architectural place of possibilities, is perhaps exactly where to come to terms with Hugh’s design sensibilities. Or, said differently, his life aesthetic.

The space Hugh envisioned shaping didn’t involve prescription, let alone perfection. Instead, it spanned effortlessly to encompass the setting in motion of imperfections: Everything was welcomed in the moving construction of possibility. This also meant that while everything could be included, some threads didn’t find themselves interwoven— and, that was ok, too.

The courage to connect doesn’t always require altruism, a contentious subject that Hugh and I would argue about, but it does require, no matter how you look at it, a measure of faith. Faith in the people. Faith in the ideas. Faith in the community making those connections. Hugh had faith. Wild, magnificent, impatient faith.

Connections across different functions, demographics, geographies, etc, can often to lead to healthy collisions. Hugh fanned the flames of these encounters, carefully stoking their embers. Of course, these connections, often immediate and abrupt, could lead to unforeseen, rather incendiary consequences.

“Was Rosebud not always inflamed from the start?” I’d express to Hugh.

The third story I’d like to share revolves squarely around the etymology and philosophical heritage of the term “possibility.”

With my background in philosophy and Hugh’s background in politics, we’d encircle the terms “possibility” (Plato) and “potential” (Aristotle) for years, often sending each other references, whimsical notes, jokes and insights, each provoking the other to reconsider their stance.

When Hugh launched the Institute of Possibility, for example, I remember sending him a card that read, “Congratulations! There’s so much potential.”

“You know, Hugh,” I’d chide, “possibility has these set of connotations …” And I’d list them out one by one.

“Yes, Yes,” rejoined Hugh. “But, what about …”

What I later came to learn, and perhaps I’m just now fully coming to terms with, is that while Hugh recognized and took stock of the importance of these historical lineages, he created his own philosophy, his own sense of possibility: a toolbox of concepts he’d readily use to connect ideas, communities and people, in a swirling concoction of his own imagination.

Possibility was his place, the encounter and provocation to live a creative life.

When he invited well-known architects, poets or scientists to visit our communities and share their stories, it wasn’t about collecting autographs or admiring their physical presence. Rather, it was about creating opportunities for rupture, signifying the possibility of a connection, and then, once established, figuring out a way for us to sign our collective signatures toward something else. Essentially, to inspire others to find and make their own connections.

For example, I remember standing at Falls Park in South Dakota with a renowned designer, watching the Big Sioux River cascade over the rocks. After a few moments of observation, this individual made a connection between Sioux Falls— which had used local quartzite to build its downtown— and Jerusalem, where local limestone was used early on as the source to build its own community. The designer had made the reference to extend a thought about the similar composition of cities, the point of which highlights rather succinctly the juxtaposition of encounters.

For Hugh, possibility was discovered in these moments as an opening in opportunity: a place or moment or event in which everything was laid bare. Then, two things, or maybe more, come together, sometimes by chance, sometimes by circumstance, sometimes by change, to remind us of the power of living a creative life.

Over the years, Hugh and I would exchange a flurry of notes, ideas and references. Sometimes sporadically. Sometimes rigorously. Always intentionally. We’d constantly send one another inspiration. Books from him would arrive at my doorstep. Books from me would arrive at his.

If the time between our exchanges had surpassed, it invariably resumed. That’s how it went between the two of us for the better part of two decades. Back and forth, accumulating an archive of inventiveness. We’d happen upon innovative and unexpected ways to approach problems, remembering the nuances of our ongoing conversations, hurriedly sending those discoveries along.

On top of points of inspiration, we’d also share things of a more practical nature: ways to organize meetings, structure conversations, optimize and evaluate performances, grow a business, etc. I’d recently suggested that Hugh check out a newly published book with tactical advice on how to build a company. It was probably the least seductive reference I’d ever sent, but it came at an opportune time.

“This is exactly where I am right now,” shared Hugh. “Can’t wait.”

Angela and I were recently unboxing some old notes from Hugh and came across an original, handwritten sketch from him:

“A creative life— especially one focused on community— requires connection: to place, to ideas, to other creatives, to a community of support.”

A mentor, a friend, a confidante, Hugh was a thought partner to so many of us, all the way up until the very end. Invariably, he was the type of person with whom you could ask advice and readily share untamed ideas. He’d listen as intently as he’d share. He brought us together and infused us with a sense of possibility. He still does, as we gather around his legacy. So many ongoing conversations.