Connection Takes Work. Our Tech Makes It Harder.

“I just had a breakup two days ago.”

The woman sitting next to me on the couch looks down, hands clasped together, as if holding the confession she had just offered. She’s wearing a tan striped dress, and I can sense a weariness in her eyes, even as we both strain to keep eye contact beneath the high afternoon sun. We had only just met, awkwardly cobbled together as the rest of the conference attendees broke off into other larger groups. There were conversations swirling around us about business, journaling, and even God—but ours was about relationships. It was just the two of us. Not what I expected on a sunny Friday afternoon at a conference of community builders, ostensibly about life hacks. Yet here I am.

I nod, my brow furrowing, and I tell her I’d recently gone through a breakup myself. My husband and I separated six months ago, and I know heartbreak well. I’m better now, I tell her—but I still feel like I’m walking around with an emotional limp. We share a tender look. The silence between us hangs a little longer than typical, and we continue talking. A clearing has opened, and we go deeper. We start discussing somatic work and what it means to be vulnerable with our bodies, how to build intimacy in group spaces, the effect technology has on our kids and the social fabric. As we move from topic to topic, I notice my jaw loosening, my shoulders relaxing, my gaze softening. Though uncomfortable at first, by the end of our conversation, our dynamic has transformed. I feel relieved—a bit more whole again.

I feel seen.

Burnout and grief are familiar company these days. Not just in the realm of romance, but across so many parts of American life that many of us—liberal metropolitans in particular—seem hard pressed to fully confront and digest. Retirement portfolios have contracted. The specter of economic recession looms overhead. Fear and overwhelm lace our conversations about politics and technology. The devastation of COVID and the climate crisis continue to be ever-present backdrops. For many of us, collective disillusionment has given way to anxiety and exhaustion. Yet we carry on. Grin hard and hustle harder, we think. When I get my bag and finally feel safe, then I’ll rest. Then I’ll have time for my friends and my community. Just keep your head down and keep going.

Our technology makes this landscape even harder to navigate. The drive to achieve and survive has only been offset by the temptation to numb. We’re too burnt out to do much else, so we keep scrolling, keep tapping, keep streaming. Another episode of Black Mirror. A few more minutes in bed scrolling before I brush my teeth. For me, the screen is little relief—but it’s hard to resist the lure of a good laugh or another headline when it’s just a few taps away. I’m not here to say that all numbing is bad—we all do it, and we all need it sometimes—but it feels like we’ve all entered into a techno-Faustian bargain: wealth and freedom as the collective promise, as long as we wake up to a screen, work on a screen, and wind down on a screen. Rinse and repeat.

So what do we do when all our energy is spent running the race, and our digital salves leave us emptier than before? I keep thinking back to that conversation at the conference. What made it feel so rare, so relieving? It wasn’t intellectual stimulation—I get that often enough in my work. It wasn’t the comfort of a shared history—we had just met. The answer is quieter than that: it was courage. Her willingness to offer something real, something raw, without any guarantee I would honor it or reciprocate, created the conditions for real connection. In doing so, she made space not only to release some of her own grief, but for me to meet her there with my own.

Her vulnerability reminded me that meaningful connection is hard won. That in relationships, effort may not necessarily be a bug but a feature.

Our industry is obsessed with removing friction: seamless flows, one-tap engagement, growth-at-all-costs. In the process, we’ve flattened much of our social contact down to likes, one-line replies, and back-to-back 30 minute Zoom calls. In our quest for efficiency, we have cheapened connection. It’s why a handwritten note seems to have more meaning than an immaculately designed but printed card. It’s why picking someone up at the airport can feel more generous than paying for the most luxurious option on Uber. There are some kinds of work I do not want technology to do for us. Instead, I’d like more technology to give us more and richer opportunities to do the work. The labor of love, of expressing thoughtfulness in reaching out, is precisely what gives value to our bids for connection. The question is whether we’re willing to build the kind of technology that honors that understanding.

I am, and I know there are others out there building it too. I think we are in the middle of a seismic shift in the culture, where what is authentic, emotional, and handcrafted has more and more value as an equal and opposite force to the inevitable hyper-optimization of technological progress. I think the future is in synthesizing these two forces. In my explorations, I’ve been searching for ways AI can make connection more thoughtful, more courageous, and easier in the right places. As I get closer to my answer in this journey, I expect to share more here soon.

This is the work. And it’s worth doing.