Memorial Day 2025

Some long weekend thoughts...belonging is older than language. As our tools get smarter and teams smaller, the question isn’t what we can build alone—but what we risk losing together.

I spent Memorial Day Weekend in a group of six people: three couples, lazily grazing white wood floors and cookie-crumb-littered countertops that smelled like a Northeast summer. Six is a good number…enough for quiet mornings where someone else has probably already made the coffee, enough to play four rounds of Fishbowl, enough to smush comfortably into a car to pick up pizza for dessert. To be honest, I’ve always been a little skeptical of group trips with couples. My going theory is that having your safest person in the room can make it easy to default to the familiar, to share less. Empirically, though, given the easiness of the weekend, the way it settled into its own regenerative flow, I might be wrong. And so I found myself wondering: was it something about the number? Or was something else quietly at work beneath the surface?

We all know the adage: two’s company; three’s a crowd. The three-body problem is famously unstable. Vogue recently published a piece titled “If The White Lotus Teaches Us Anything, Let It Be This: Never Take a Three-Person Girls’ Trip.” In other words, triadic tension tends to wobble, and someone always ends up orbiting. Four is more stable, but can split into predictable pairs. Five is tricky with a “swing vote” dynamic. But what about six? No laws of nature are compelling you into any one configuration: you can be three couples, or two triplets, or, in poetic terms, a quatrain and a couplet (the closing 6 lines of a Shakespearean sonnet), or a complete sestet (the closing 6 lines of a Petrarchan sonnet). Like a jazz sextet, to borrow this time from musical terms, there is harmony with responsibility in every note.

Still, numbers alone don’t guarantee intimacy. I’ve been in groups of three that felt expansive, and in groups of eight where no one said anything real. Anthropologist Robin Dunbar might explain that it’s a question of cognitive load. His research suggests our brains are wired for layered social circles (interestingly in multiples of five): five intimate ties, fifteen close friends, and fifty meaningful connections. But intimacy isn’t just about who fits in which layer—it’s about how fluidly people can move among them. Some of the most electrifying moments happen in the liminal space, when someone who was once a plus-one becomes a confidant, or when two people make an unexpected connection that shifts the group’s center of gravity.

The fabric of intimacy. There’s a specific kind of intimacy that lives in the pause before someone speaks. Silence can be deeply meaningful when met with attention—when we bask in the safety it invites. I think these brief moments compound, like a symphony of micro-calibrations that move a group from coordinated to connected. Human glue made of shared time, and maybe a second glass of wine.

Intimacy also scales through narrative. The Science of Storytelling explains that humans bond through the stories they share. Every group has an implicit script: heroes vs. villains, what the good guys are fighting for, and how gravity works in their world. To belong, you internalize the story. To matter, you become the protagonist. In his writings, Yuval Noah Harari uses the term "imagined orders" to describe shared beliefs and stories that humans create to organize society and assign meaning to things. These imagined orders (e.g., myths, religions, laws, and ideologies) enable large-scale human cooperation by shaping trust and understanding. They are based not necessarily on objective truth, but rather on collective belief. It’s how Theranos was able to raise $9 billion—not because the tech worked, but rather because people wanted to believe in the myth of a “female Steve Jobs.” More than just backing a diagnostics company, they were buying into a modern reimagining of an old origin story.

For all the ways in which technology has abstracted our connections, there has been a growing hunger to feel something real again. You can see it in the resurgence of supper clubs, the way we romanticized analog hobbies in 2020, the therapy-speak that’s crept into Hinge profiles (@beam_me_up_softboi for a belly laugh). In a post-(acute)-pandemic, post-remote, post-“hustle culture”, post-hypergrowth moment, people are finally asking: what if intimacy is the point?

In one of TikTok’s/Instagram’s many viral trends, one reel format that has emerged is the collation of the small moments in life—the moments of intimacy we share with our friends, with our partners, with our children, with our animals, with nature—bearing the caption, typically in all lowercase letters: “almost forgot that this is the whole point.” The reels are set to the first few notes, played on the piano, of “Take My Hand” by Matt Berry. The trend is a collective invitation to intimacy—to take each other’s hands, to whisper in lowercase voices, to remember why life is worth living.

After decades of designing for efficiency and scale, of getting more done with fewer people, maybe we're starting to remember—and to protect fiercely—the quiet joy of building deliberately, with people we trust. Move fast and break things met with move slow and nurture things.

And yet, as our personal lives bend toward reconnection, the workplace drifts the other way. The age of the deployment of AI agents means that more and more, white-collar workers find themselves leading tools rather than teams. Or the “team” becomes a silent stack of models, plug-ins, and prompts. Ted Chiang writes that AI is a form of lossy compression—it preserves what we can measure and discards the rest. Like a JPEG that blurs subtle gradients in service of saved storage, AI smoothes the interpersonal mess that comes with collaboration in favor of saved costs.

In Singapore, nearly 1 in 5 full-time workers are projected to be displaced by automation in 2028—the highest rate in Asia. It’s perhaps unsurprising for a country that’s long stood as a global emblem of efficiency and innovation. But this projection points to a deeper reckoning that most advanced societies will have to confront. As tools become more capable, it's no longer a fantasy to imagine a one-person, multi-agent, billion-dollar company. What once took 100 people to build now takes just 1. So if AI renders 99% of knowledge-work obsolete, what is left for our knowledge to do?

The Marxian prediction feels more prescient than ever: alienation as the inevitable consequence of labor, divorced from its social and creative roots. In this new paradigm, human-to-human interaction will matter more, not less. And the companies that build for this end, where people feel seen and needed, will be the ones that endure. So the fundamental question to ask is: how do we design for this new world? Do we focus our recruiting efforts on joining companies that preserve human connection, through product or through culture? Create them ourselves through distributed leadership and community-first design? Or fund the next generation of institutions that don’t just run on output, but on culture?

Maybe what I meant to talk about here isn’t optimal group size, but rather the optimal conditions for intimacy—how we create it, how we lose it—and the absolute necessity of it. The future of work may be an automated, asynchronous place, but the ancient circuitry of belonging will always endure in our brains. In the end, whether it’s a startup or a six-person congregation on Memorial Day, maybe it’s the means that gives the whole end meaning. To feel seen, and connected, to be part of something with a beating heart.

There’s a poem by James Wright called “Lying in a Hammock at William Duffy’s Farm in Pine Island, Minnesota.” The long, particular title summarizes the project of the poem: he describes everything that he sees lying in this hammock in great, loving detail. This attention is a kind of intimacy, a communion with the present moment, and all of its inhabitants. After this extended exercise in devotion—almost prayer—he concludes: “I have wasted my life.” In other words: he has spent his life in a forgetful haze, failing to remember that this attunement with our very world—noticing the peculiar way the butterfly sleeps, noticing the fading sound of the cowbells as they “follow one another / Into the distances of the afternoon”—is the whole point.