I’m what you might call “a nice guy”. I believe in fairness and kindness and giving people the benefit of the doubt. But my frustration levels were a bit higher than my normal baseline because I was trying to get to work on time, and the first Uber I called just sat there in one place for 5 minutes. I texted, and called, and no response. Okay, I thought, cancel and try again. The driver who responded next had a 4.38 rating. Ouch, I immediately thought. Well, I’m sure it will be fine (for comparison, my average rider rating is 4.96 stars – someone somewhere docked me slightly, keeping me from a perfect 5…).

Our house is notoriously mislabeled on GPS, so I always go to the end of the driveway, wear bright colors and hold signs with flashing lights that say “I’m the one who called Uber! Please stop and pick me up!”. I spotted Mr. 4.38 (the app told me his name but he had become a number to me – a subpar number at that) and frantically tried to wave him down, to no avail. He blew past me and turned left at the light, and I ran after him down the sidewalk. I managed to get his attention and get him to stop – in an extremely inconvenient spot on a very busy road. Cars behind him were honking and racing around him. I signaled for him to pull into a driveway on my side of the street so I could get in safely and to prevent him from blocking traffic further. So, yeah, things weren’t going great so far.

After I got in, though feeling bad the whole time, I judged him on a number of factors – I couldn’t understand him clearly when he spoke. His speedometer seemed to be in kilometers per hour – there’s no way we were reaching the speeds the digital readout purported. His driving was erratic – accelerating too much, breaking hard – I felt on the verge of being carsick (which is something I never experience). We came to an intersection, and I told him to go straight – and go straight he did – straight through a stop sign into a particularly harrowing intersection. It was at that moment I made up my mind, in the midst of my guilt – I’m only giving him 4 stars.

This internal drama may not resonate with those more attuned to a logical, black and white sense of justice – anyone who blows through stop signs either lacks the environmental awareness to see and respond to them, or is aware and doesn’t care – either of which are troubling driver behaviors and deserve to be judged accordingly. But the way I’m wired, there’s a part of me that wanted to help this person, for all the same reasons that I judged him earlier. I want this person to do well and succeed in life. But I also needed him to perform a service (for which I’m paying the company that contracts with him) safely and reliably. I left the car in a huff. Why did he put me in the awkward position of having to give him less than five stars?

Fast forward to a few days later. I’m trapped in my office building because the smoke from wildfires hundreds of miles away has drifted into Atlanta – a blanketing haze ominously settled amongst the landscape of skyscrapers and countless lanes of traffic. I decided Uber eats is the most convenient, least smoky way to obtain sustenance. I open the app and decide quickly on “The Feast” from a mediterranean place called Bezoria – a smorgasbord of every good thing you might order from such an establishment in one delicious package. Things were going well – the driver seemed to be on track. And then, and then. Then I saw him get onto the highway and head north out of the city, completely in the wrong direction. When he finally arrived, I was “hangry,” and wanted to dock him for his navigational failures with the dreaded 4-star rating. But there was something about his harried look that made me change my mind. I opted for mercy and gave the full 5-stars. When I got back up to the office, eager to tear into my Feast, I noticed the pita bread I ordered was missing. Ugh.

There’s so many moral and ethical questions I wrestle with regarding the gig economy. Does it provide “a living wage” (such a dubious phrase) for those who have been unable to find work elsewhere? Should Uber drivers receive health insurance and other benefits? The drivers themselves seem to be torn on that question, because I often ask what they think about the ongoing legal battles facing their employment status. Most seem unwilling to go down that road (pun intended) – the whole reason they drive Uber is for flexibility – they aren’t interested in a traditional employer / employee relationship.

And then, of course, there’s the transparent plan to replace all human gig economy drivers with autonomous vehicles. What will those people do to earn an income when this becomes a reality? Will they go back to what they did before, or will the gig economy evolve to create new opportunities that automation can’t so easily replace?

I enjoy talking to Uber drivers and asking them questions. I normally dislike small talk but I try to rise to the occasion. I want to thank them for performing a valuable service that enables my wife and I to share a car and save thousands of dollars every year. I want them to know that I appreciate their help on a very human level, and that as a guest in their vehicle, I respect them and want to make the best of our short time together (amazingly, or perhaps not due to Uber’s massive recruitment efforts – I’ve never got the same driver twice).

And yet. And yet. Everything about the service is designed to dehumanize the relationship (of course, this is in light of the rise of the machines – I’m referring to autonomous vehicles, at least initially). Yes, there’s a rating system – but that too is so automated. We are used to rating apps on a five star scale. There needs to be just enough trust and fellow human feeling that I’m willing to step into a stranger’s car (something mom told me never to do!). Beyond that, though, the human is deemphasized and the technology takes center stage. It’s so interesting to me that very few Uber drivers ask me if I have a preferred route. They mainly blindly follow their navigation app of choice (Google Maps dominates, followed by Waze). This is troubling to me. It’s as though they are too willing participants in their own dehumanization at the hands of a multi-billion dollar company.

The trouble is, I want automation in some parts of the experience – automated driver selection, cost structures, cashless automatic payment, etc. For example, I don’t want to have to pick my driver among all those who respond (which would open up a whole other arena for discrimination…). But those features are just table stakes for a good product. Beyond that I want a human being making human decisions with human awareness of both driving and creature comfort sensibilities. For example, asking me if I have a preferred route, if I’d like music or not, if the temperature is ok – all these questions might be annoying and unnecessary to some people, but to me they speak to something beyond what technology can deliver to me today (of course, the current app has Spotify integration, which I don’t use, but I can imagine in the autonomous car future scenario, I’ll be able to pick the route I want the car to take, play any of my music from any source via the car’s stereo, and manage the car’s heating / cooling, etc.).

Technology creators and users must wrestle with the implications, often not obvious, in the  interaction between people and their technology. Om Malik wrote in an article called “Silicon Valley Has an Empathy Vacuum” that “Silicon Valley’s biggest failing is not poor marketing of its products, or follow-through on promises, but, rather, the distinct lack of empathy for those whose lives are disturbed by its technological wizardry.” Should we think of technology purveyors like prosecuting attorneys, whose main goal is to build the strongest case (product)  at any cost? Or is there room for taking lessons from businesses like Warby Parker, Toms Shoes, and other “social enterprises” who make it a core part of their DNA that for them to win as a business means that those who cannot afford basic consumer goods like shoes or glasses receive them as a matter of course? Could Uber survive as a business if for every paid ride, they allow a free ride to low-income senior citizens to the grocery store and back? Could AirBNB offer free stays to families in need of a roof over their heads until they get back on their feet? When does it make good business sense for margins to be in conversation with empathy, so in the end more consumers actually have the means to afford these products and services, effectively expanding the user base so everyone wins?

The market inevitably decides winners and losers – both from a business and people perspective. Every day we vote with our wallet and shape our future – and increasingly we choose low-cost automation that delivers on speed and efficiency while downplaying or eliminating the human elements involved. Technology is wonderful and amazing and improves our lives in countless ways, but it also disconnects us from basic reality. As we deny the humanity of others through technology, we also deny our own. We make this Faustian deal as long as we find ourselves on the winning side – but what should happen if we end up on the other?