A high tech, low touch journey through San Francisco’s transportation layers—from legacy taxis to runaway Waymos—and what it reveals about empathy, experience, and the systems we’re building.
It’s December 1st, 2025, and I’m exhausted. I just flew from Boston to San Francisco on a reverse red-eye. Normally, I sleep well on overnight flights. On a plane, on a train, in a box, with a fox—I can sleep just about anywhere. I fall asleep as we taxi onto the runway and wake from the bump of landing. It’s one of my few superpowers. I can time travel.
But tonight, I couldn’t sleep. Maybe it was tomorrow’s event, or the joint pain I usually ignore (I was born with Juvenile Rheumatoid Arthritis, isolated—luckily—to my right knee), or leaving my family for the first time after a restorative sabbatical. Something kept me up. Now I’m standing outside SFO at 1 a.m. (4 a.m. in my head), and our Uber isn’t getting any closer.
I’d run into an old friend at Logan before takeoff—Jonathan Desrosiers, longtime WordPress core contributor—and now we were waiting together in the cold. California was expecting a rare cold snap, which I have no doubt Jon and I brought with us.
Jon was telling me about a new way Uber drivers game the system:
“They wait outside the airport and accept rides with no intention of moving. Eventually you cancel and they take the cancellation fee.”
Sitting there watching the unmoving car icon, I grew impatient. This isn’t the stoicism I try to embody, so I took care to be empathetic when I contacted the driver. “I’m coming!” was the only response I got. It was my first reminder of what happens when modern transportation becomes high tech low touch.
Meanwhile, a black Civic pulled up beside a young blonde woman. The driver rolled down the window and said, “Taxi? Your Uber is going to take all night.” She declined. Her radar was up. The whole situation felt off. Wanting to test my own assumptions, I caught the driver’s eye and said, “I’ll take a ride.” He rolled up the window and sped away.
Jon and I looked at each other and wondered how close that woman might have been to danger. No way to know for sure, but nothing about the encounter felt right.
From High Tech Back to Low Tech
With no further response from our Uber driver—still a stationary icon on the map—we went looking for a taxi stand. At this rate we could walk across the airport and back before the Uber reached us. Minutes later we were in a privately owned livery SUV heading downtown.
Jon and I talked with the driver about what he’s seen over the past two decades and what he thinks of Uber. He’d tried it for a while. With a fleet of luxury SUVs, Uber Black made sense for him. He made money until Uber dropped the premium payouts and tightened margins.
“We stopped making money on Black. Something changed and it no longer made sense. Uber is too focused on cutting every corner. We make pennies.”
It was an odd juxtaposition: being driven through the global epicenter of future tech in a traditional livery SUV. I thought back to when Uber burst onto the scene at exactly the right moment. Taxi services were begging for an overhaul: miscommunication, language barriers, impolite drivers, cash-only policies. Uber had the right model, enough capital, and a simple answer. It made early riders feel special.
But now the energy behind the novelty has faded. Taxis have adapted. They have mobile credit card readers. They’re friendlier. They know the roads and shortcuts better than anyone. And a taxi stand with a dozen waiting cars beats any app. Uber’s lead is shrinking, and user experience is the first casualty in the battle between tech and drivers.
And in a twist I hadn’t expected, the luxury SUV ended up cheaper than Uber’s estimate. They aren’t even winning on price.
Going Higher Tech
The next morning I woke earlier than expected and headed to the breakfast buffet at the Hilton Union Square. Side note: I’m trying to replicate those Hilton-style scrambled eggs at home, so I always take time to savor them. I journaled, drank coffee, saw colleagues drifting past, and soaked in the energy. We’d all flown in for the annual State of the Word, an event I’ve been lucky to attend more than once.
After breakfast I put on my new suit. A hundred pounds of weight loss in a year means new clothes. I headed downstairs to find a ride to the Automattic lounge known as Mission. This time I opted for something even higher tech: a Waymo.
It felt strange to return to high tech after the taxi had salvaged my previous experience, but I’d never been in a self-driving car. Bucket list opportunity.
I like to time my walk to the lobby so the car arrives just as I reach the door. It makes me feel mildly cool. The Waymo beat me. These cars are everywhere.
My initials rotated around the LiDAR unit to confirm it was mine. I unlocked the doors with the app, got in, and hit “Start Ride.” The car reminded me it doesn’t listen to conversations and that I should buckle up. Ignoring that triggered the seatbelt alarms within thirty seconds.
Overall, the ride was fine—clean, comfortable, safe. But also strangely empty. The most notable thing about it was that it was driving itself. And what surprised me was how much I missed the conversation. Drivers tell stories, share perspectives, offer glimpses of their lives. You learn about people. Waymo offered none of that.
I used Waymo a few more times that day. At one point it struggled with a tricky drop-off and we ended up walking a few blocks. Still fine. But the novelty was doing all the heavy lifting.
State of the Word
The next day was the State of the Word, dozens of stories above sea level with sweeping views of the Bay. Seeing colleagues I rarely get to see made me happy. The conversations were rewarding and energizing. I was there to represent Automattic and WP Cloud, and I found myself in great discussions with partners and potential partners. I also recorded an interview with webhosting.today.
Watching demos of Gutenberg’s future and AI site building, I reflected on my own path. More than 20 years ago, my former professor turned colleague, Hilary Mason—who went on to run bit.ly, founded Fast Forward Labs, and now leads Hidden Door—once said, “Have you heard of WordPress?” That single comment set my trajectory.
I fell in love with WordPress. The community was welcoming. The mission to democratize publishing resonated deeply. And it was a joy to code on.
If you had told my younger self—sitting at my adjunct professor desk—that I’d someday build a career on WordPress, write books on it, co-found and sell a WordPress security company to Automattic, and eventually run WP Cloud, all while attending the event of the year high above San Francisco, I would’ve laughed.
Which made me wonder what my future self would tell me now. We can try to plan our lives, but certainty is a myth. Patterns and trends are the most we can hope to understand.
Men tracht, un Gott lacht. (Men plan, God laughs)
Yiddish Proverb
My reflection was disrupted when my phone started vibrating. The livestream had failed. Despite being in one of the world’s most technologically advanced buildings, the internet connection wasn’t strong enough. As a precaution, the team had used a high-tech bandwidth fusion setup combining cell signals and Starlink. It didn’t help. For a while, the livestream was a silent black screen.
A telling irony.
When the Loop Breaks
After the event we headed to the afterparty. We had Uber vouchers, but the wait was long, so we called a Waymo.
We should have known something was wrong when it stopped in the middle of a busy road to pick us up, halting traffic. We got in anyway. Energized from the day, we fell into a deep conversation about WordPress, the community, and the future. Without a driver, we talked even more freely. We weren’t really paying attention to the route.
At some point, the car veered off its straightforward path and entered a rough part of San Francisco. The streets were filthy. People experiencing homelessness lined the sidewalks. Drug deals happened openly. Human acts usually kept private were out in the open.
None of this is judgment—just reality we witnessed.
More concerning was the realization that we had passed the same bodega three times. The car was circling. On the first pass, a man was using the sidewalk as a toilet. On the second, the shop owner was yelling at him. On the third, the owner was pouring chlorine to disinfect the concrete.
Above all this, towering billboards advertised the future of AI.
The juxtaposition was unbearable. On the ground: people curled together for warmth in one of the wealthiest cities on earth. Above them: glossy promises of technological salvation, completely disconnected from the human suffering just feet below.
The ethical message seemed lost on the companies behind those billboards.
The Waymo continued its loop until we finally got stuck behind a double-parked UPS truck. Only then could we reach support through the dashboard. Our call went to someone halfway across the world, who escalated it to someone “who can take control.” Eventually, they remotely steered us out of the loop. We arrived thirty minutes late.
Waymo offered a five-dollar credit.
A fractured experience, neatly summarized, and a perfect example of a high tech low touch system: impressive from afar, indifferent up close.
The Cost of Cutting Costs
Here’s what stayed with me afterward: every major tech company right now is aggressively cutting costs. Optimizing for efficiency, automation, and frictionless transactions. On paper it sounds good. In practice it erodes the experience.
Uber succeeded because taxis had grown complacent. They were inconsistent, cash-only, and often unfriendly. Uber felt fast, transparent, fun. But eventually the company began optimizing for itself—squeezing drivers, raising prices, cutting corners. Drivers adapted by gaming the system. Riders became collateral damage.
Meanwhile, taxis improved. They cleaned up their act, added card readers, and rediscovered the value of service. They remembered that the rider is their livelihood.
Waymo promised the next evolution: a ride with no driver at all. But removing the driver also removed accountability, adaptability, and human judgment. When the car gets stuck in a loop circling the Tenderloin, there’s no one to notice, no one to care, and no one empowered to fix it in the moment. Just a remote support rep and a five-dollar credit.
High tech, low touch.
What We’re Losing
We’ve optimized away small daily interactions: clerks, baristas, taxi drivers, bank tellers. We’ve replaced them with apps. These conveniences save minutes while quietly weakening our social muscles.
We’re losing the ability to see one another, tolerate one another, care for one another.
For leaders, this matters. Empathy doesn’t come from thinking about users as data points. It comes from interacting with them—hearing frustrations, understanding context, feeling the weight of their experience.
When we strip human connection out of our systems, we lose the feedback loop that keeps us honest. We stop noticing when things break. We stop caring.
The billboard above the homeless encampment wasn’t just ironic. It was symbolic. Companies promising to save the world with AI are the same companies building systems that make us lonelier and less connected. They’re solving problems they don’t see because they’ve removed themselves from the people they claim to serve.
The Taste We’re Losing
We often tell people who dislike a new food that they need to develop a taste for it. The complex, challenging flavors can become the most rewarding.
Humans are similar. We can be complicated, frustrating, beautiful. We become more human by being with one another.
We’re losing our taste for complexity, and therefore for each other.
Empathy is an acquired taste, developed through contact—not avoidance. When we design systems that strip away connection, we dull the senses we rely on to lead. It creates a loop: isolation breeds less empathy, which leads to worse systems, which leads to more isolation.
And who benefits from that?
Not us. Not the people we serve. Not the future we hope to build.
A Different Model
What gives me hope is that I didn’t fly to San Francisco to witness the failures of high-tech systems. I flew there to celebrate something that’s quietly succeeded for more than two decades: WordPress and the open web.
The State of the Word wasn’t just a recap. It was a reminder that another model exists. WordPress powers over 40 percent of the web through a philosophy rooted in collaboration, community, and service.
At Automattic, everyone does support rotations. Engineers, designers, executives—everyone spends time helping customers. It’s not a gesture. It’s a belief: you must know your customer and build for their needs.
Not investors’ needs. Not growth metrics. Their needs.
This breaks the isolation loop. When you’re required to interact with the people you serve, you can’t reduce them to data points. You have to see them. You have to listen. You have to care.
Open source demands this. No algorithm stands between contributors and users. There’s no pressure from venture capital pushing toward extraction. There’s a community building something together, one contribution at a time.
The open web shows we can build systems that connect us rather than isolate us.
The Way Forward
The taxi driver who picked us up at SFO didn’t just get us to our hotel. He talked with us. He shared his life. He reminded us that technology is only as good as the experience it creates for real people.
That’s the lesson I brought home: high tech doesn’t mean high quality. Low touch means we lose something essential—something no automation or five-dollar credit can replace.
We drift toward high tech low touch environments when we stop designing for real people, but don’t have to accept this trajectory. We can design systems that keep us connected to the people we serve. We can choose collaboration over isolation, empathy over efficiency, community over convenience.
The open web isn’t just a technical architecture. It’s a social one. It’s proof that remarkable things happen when we refuse to lose our taste for each other.
If we want to break the loop, we have to design for contact, not avoidance.
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