Rosemary and the Very Long Ride

Date: September, 2021

Two years ago, I took an Uber ride that changed the trajectory of my career.

At the time, I was fresh out of law school and researching technology and innovation policy for the Center for Growth and Opportunity. I was writing articles and publishing, but nothing major until a friend of mine invited me to a happy hour with a group of prominent tech policy experts. 

Many of their follower counts on Twitter were larger than the population of my hometown, and I was understandably very nervous. That was when I hopped in the back of my Uber and met Rosemary, whose graying hair and polite insistence that I buckle my seat belt made me feel like I had climbed in the back of my grandmother’s Oldsmobile. 

She had two pink index cards taped just under her media console, and she struggled to follow the directions displayed on her phone’s GPS. Because I was already running late, I offered some help with a possibly illegal u-turn, which is when she shared with me that she had received her first few tickets in D.C. just in the past year thanks to the inundation of traffic cameras installed.

As I’ve come to learn in the time since, once you start a conversation with your driver you open up the door to learn more about them. If you’re willing to listen, you can learn a lot. 

The first little bit I learned about Rosemary, aside from her traffic violations, was that she taught mathematics and English to students for whom English was not their first language. 

She then asked me if I was going out to meet some friends, which is where things got interesting. 

I have a personal rule that I don’t lie to my Uber drivers because it makes a conversation dull. So, sticking to my rule, I was honest and said I was going to a tech policy happy hour. 

Immediately after I said it, I knew I was in for a wild ride. Her eyes widened, she looked me directly in the eye through the rearview mirror and said what I can only clumsily paraphrase now as: “You know the power of these big tech companies has gotten immense. At this point, I don’t see how they aren’t regulated because they control so much of our society.“

We debated it for a while, with my position falling on the side of industry self-regulation and her falling on the side of skepticism. Then she asked me the dreaded question I was hoping I could avoid: “So, which side do you work for?”

Somewhere in the conversation I had already given away that I was a lawyer working at a research center. But she wanted to know more, almost like a sixth sense was telling her I wasn’t telling her the whole story. She wanted to know who paid my bills, how that affected my objectivity, and even who I voted for. 

I stuck to my rule. I was open about all of it. The primary reason at that point, however, was that I thought if I lied she might throw me out and after a couple more missed turns I was running very late at that point. 

That’s when Rosemary shared the rest of her story with me. 

Rosemary was playing coy. I came to find out she held a master’s degree and a law degree, was married to another lawyer who helped bring down a major Pentagon bribery scandal, and had a daughter who was a chemical engineer. She was also an Independent, much like myself, and intensely engaged in current events.I loosened up a bit after concluding she wasn’t going to kick me out, and we debated domestic policy and foreign policy. Most of the time Rosemary won and I listened, knowing full well that I had met my match. All the while, we missed turn-after-turn and added many more minutes to a ride that should have taken only a few. 

I was very, very late. I missed some connections. But I loved every minute of it. 

On one hand, Rosemary was interesting, with layers of complexity that she was more than happy to share with me. On the other hand, when she eventually dropped me off at the happy hour I had been so nervous about before, I felt confident and personable again. I gave her my card, walked into the bar, and made lasting connections with people who intimidated me only thirty minutes before.

After Rosemary

After a few days, it became clear that my ride with Rosemary was not going to be forgotten. I began to wonder why experiences like that aren’t more frequent. And as I went back to researching tech policy, I began to ask myself what platforms could do to make working in the gig economy just a bit better, a bit more reliable, and a bit more meaningful. 

One thing that stuck out immediately was a lack of group health insurance.  For part-time gig workers like Rosemary, this coverage is typically available through their full-time employer. For others, it is available through a spouse or a parent. But what about the others? “What a massive hole in the market!” I thought.

Then I moved on to other things, like car insurance. I thought that rideshare platforms offering automotive insurance to drivers might give them a competitive edge. Afterall, I reasoned, car insurance is expensive, and when a thirty-minute ride only pays $8-$10, insurance probably eats up a good portion of a driver’s income.

I went on and on, finding different ideas for platforms to improve the gig working experience. But I thought the issue was a lack of funds, especially since many gig platforms were still borderline unprofitable. It wasn’t until I simply Googled, “examples of gig platform insurance plans,” that I realized the bigger issue. 

Far from a bad corporate policy, I discovered that platforms can’t offer health insurance plans, thanks to a rigid set of employment laws. The line between a gig worker, with all the flexibility enjoyed by people like Rosemary, and an employee — which would cause platform costs to skyrocket — is thin and volatile.

But far from a worker classification problem, as I came to realize when I started seriously working on this policy issue, it is a problem of clarity. If we could simply offer some legal clarity to platforms by nullifying the effect of benefits contributions on the legal test, we could eliminate the problem. Put another way, if we could get regulators out of the way, we would see platforms fill in the coverage gaps and attract more workers into the gig economy full time.

Fortunately, I didn’t stop there. Once I became vested in the gig worker problem, I wanted to learn more about what needed to be fixed — this time at a regulatory level. After Rosemary, I knew the best way to find out what was wrong in the gig economy was to ask gig workers. 

I started talking to my rideshare drivers as often as they would let me. Their stories, world views, and reasons for driving have been diverse and surprising. Eventually, their stories led to what is now our Future of Work project — with the addition of benefit portability to better suit a gig work lifestyle. Our aim? To help people access the basic coverage they need without compromising their freedom to work.