A Series of Conversations with Ride Sharing Drivers

There’s a story behind every trip.

Gang Su
15 min readMar 29, 2019

I enjoy having conversations with people, but I found it becoming increasingly difficult when most of our fragmented spare time is now occupied by screens. A few years back I took a cruise trip to Mexico with my wife and we were disconnected from the network for a week — it was the best time we had for a while. We had long conversations like old times, enjoyed ourselves at the moment, and chatted with random folks who were also forced to put their mobile devices down. Other than this forced isolation from technology, one of a few other opportunities for conversations are long shared rides, especially when stuck in bay area traffic and multiple parties are willing to break the awkward silence. I sort of keep a journal in my head about some interesting encounters, and since I only have limited storage, I want to flush some them out to the web (oh, the irony) so that they can live indefinitely.

I may even revisit this thread, and add more stories as I find them. Disclaimer: this is not an advertisement, a marketing material, or anything to be associated with the rider sharing industry — it’s merely a recollection of my personal experiences, and a reflection of my personal stories and opinions, and not associated with my current and future professional employment in anyway.

The Oldman with a Purpose

You probably have noticed that there are quite a few senior drivers. Some drive for extra money, and some drive for filling free time. I remember a late pool trip from San Francisco to Peninsula one night. It was a clean, old Chevy Impala, with two passengers busy on their phones in the back row. I hopped on, and the driver was a gentle, tall African American old man with a grey beard. I greeted him, and then just like everyone else I proceeded to check my emails. He was quiet and the ride was smooth, but after a while, I decided to start a conversation to break the ice.

“So how long have you been driving?” I tossed the question. “Five years. And today — about 8 hours, and a few more to go.” He answered.

He then commenced to tell me his story. He was a veteran, and after the military service, he worked in a hospital for many years. Five years ago when he retired, all of a sudden he was confused about what to do for the rest of his life. Throughout his career, there was always a clear order or an objective to fulfill. But then, he felt he was finally free in the open field, but he lost his purpose.

“My kids grew up and left home. My wife also left me. I was all alone, and I don’t know what to do. Then I heard about Uber. I was like, heck, I still have some debt to pay, I could payback with my retirement in 20 years, or I could drive Uber and payback sooner. I don’t want to owe money when I am sleeping on my deathbed.”

Then he started his Uber journey, and he witnessed the rise of ridesharing and the fall of the Taxi industry. At the peak of incentive wars, he could earn over 10k USD a month. Those were the good times, and he enjoyed most of it. Now he doesn’t drive with as much, but still around 6–8 hours a day, making about 5–6k and enough to pay the dues. For the most part, waking up every morning and drive has brewed into his life.

Then I told my dad’s story, there are a lot of parallels — my dad also served in the military, and lead a very monotonous but stable life, and most of the time he was just following the predetermined path. When the path was withdrawn after retirement, he was trapped for a long time in the sadness and the feeling of worthlessness and bewilderment. Then he slowly recovered by seeking new hobbies and trying to stay optimistic.

“We all need a purpose. It could be a different purpose at different stages in your life, but you need one. For me, it’s to keep driving until my last breath.”

Then we arrived, and we wished each other good luck. As I walked out of the car, I noticed the passengers in the back have been listening to our conversations with big smiles on their faces. I don’t know when they put their phones down, but I felt something in my heart, and it was a wonderful moment.

Brave the Storm

It was one of those nights in the rainy season when all of a sudden a forceful storm hit the city, delivering torrential rains. I had an appointment and was trapped, at one point, a Uber ride out of SF was surged to about 150$. I couldn’t even get my umbrella open against the winds, and I desperately needed a ride home.

Then this driver showed up. While everybody else was miserable, he appeared to be extremely happy. He greeted me with a big laugh:

“Hello my friend, how are you doing today?”

Obviously not so great, I got drenched by rain already and I didn’t even want to check how much I would be paying. But I couldn’t help wondering why he was so cheerful in such terrible weather and standstill traffic. And it turned out, he was really talkative.

“You know my friend, as a Uber driver this is the best weather I could wish for. I will be driving till late tonight until the rain stops!”

Then he began to tell me his story. He was originally from Mexico, used to be a taxi driver for a couple of decades, worked long hours but wasn’t treated well. When Uber came along, he was skeptical at first but then as his colleagues left one after another, he started to think about it.

“I wanted to try to drive for Uber but I didn’t have a car. So one day, I took Uber to work. As I left Uber, I know I am not gonna drive taxi anymore.”

He then told me he loaned some money and bought a used Prius. He made some good money, saved up and bought a home in Sacramento. Every day, he drives down to SF and works for 10–12 hours. The money is much better than Sacramento due to the fierce competition between Uber, Lyft, bike/car shares, scooters, etc.

“I am super happy now! Driving long hours doesn’t bother me at all since I used to drive a Taxi for even longer shifts. I enjoy driving and taking care of my customers and I can support my family.”

The rain finally cleared. I arrived home safe and waved goodbye, wishing him a safe trip home. When I was in San Francisco the first time in 2006, yellow cabs were everywhere. But now they can only be spotted occasionally. I am glad that some drivers moved on, and enjoyed the new modus operandi.

The Father’s Mission

One evening after a stroll, we summoned an Uber home. A Jeep arrived, and as we opened the door, we saw kids sports gears everywhere. The driver, mid-aged white guy wearing a baseball cap, apologized for the mess.

“I have three sons, and I brought them to play soccer and basketball all day,” he appeared to be quite exhausted, but apparently proud and happy when talking about his kids.

He told us the kids just went to bed. He’s out again driving Uber because his sons want a brand new Xbox.

“I don’t drive often, you know this Jeep is a gas-hog. But whenever I need some extra cash I would go out and make a few trips. If I am lucky to hit the incentives then it’s not too hard to get some quick money.”

And kids need dad’s dedicated time. He got up at 6 am, took the old ones to soccer games and played basketball with the younger ones. Then he ran some errands while kids took a nap, and brought them out again in the afternoon for a hike. Then there’s dinner, a chaotic time before bed, and by 9 pm he kissed goodnight to his wife and started his mission for the game console.

“You know, a man’s got to do what a man’s got to do.” Tomorrow is Sunday, and he has another full day of fun family activity ahead of him, but he couldn’t stop at the moment. The kids and family need him, in many different ways.

It was a short trip, but we offered him a good tip and left a message — hope you will finish your mission soon, so you can go back to your kids with a trophy.

The Civilian Data Scientist

We often assume each driver is on his or her own, but occasionally there are some who go above and beyond to understand how Uber works. I have talked with numerous drivers who not only complained about certain aspects of Uber experience, but also provided incredible feedback on how to improve various aspects of Uber, such as mobile UI, trip pick-up, payments, conflict resolution, etc. I genuinely thought the designers and product managers should listen more — what customers need may not be a super sleek UI but an APP that can be used reliably and effortlessly. My most memorable experience was from a retired father — he arrived in a new Impala (Again, I especially remembered his car again because it’s not very common these days). He told me he ran the previous car to 250k miles in a few years and now his daughter is driving it as her first car in school down in Florida. He’s very cheerful and talkative; he mentioned how he attended multiple drivers’ events either hosted by Uber or organized by driver communities. He told me how many active drivers there are at the moment in San Francisco, what’s the % are full time and part time drivers, how much they are earning, how to exploit incentive loopholes, and even the adverse effect to city traffic:

“Boy, 1 out of 4 cars at this time could be Uber. They did not make commute better, they made it worse! Even folks from Sacramento are here for the surge rush! I can’t complain because terrible traffic means better money.”

“The way they compute pool trips is bad. I once had a passenger sitting in my car but never got dropped off, because I was picking up and dropping off someone else three times in a row and driving in circles! It took me almost three hours to drop her off — luckily she was just touring the city and not in a hurry. I think the Uber guys should set a limit on how many times picking up other passengers can happen while you are on a pool trip.”

I was really astonished how accurate his intuition of some trip algorithms and some of his data are. Maybe it’s not necessary to run a data query or simulations. You simply need to talk to the right people on the ground.

The Silent Smiles

Not all drivers are that talkative like the previous Civilian Data Scientist. Some are very quiet, can’t wait to deliver you from point A to B then move onto the next mission. Some may not talk at all, unwillingly.

My wife and I went for a brunch one time and we hailed one Uber. The car drove past us even we were waving and chanting. It drove around and stopped. As we hopped in, we noticed notes taped all over the car. It turned out the driver was deaf and speech impaired. He put notes at where you can charge your phone, where to grab snacks and city maps, how to plug in your phone into the car’s audio system, etc. He had a beautiful smile and drove quite and gentle. At that moment I really wondered about his life stories, what’s his life is like throughout the days and how he felt about driving Uber. Then I felt fortunate that I was part of something that provided an opportunity for him to provide for himself and his family. I don’t want to make this feel like a PR attempt here but at that moment, I did feel I what I was working on was a noble thing.

As we left the car, I offered some cash tip — at that time in-app tipping wasn’t available. He took it with both hands and nodded his head with a smile. It was a pleasant day for all of us.

A Tale of Two Cities

If you ever tried to hail an Uber or Lyft from Airport, you would find that it’s very tricky. Cars can only access certain areas with various permits and you may be trapped in some place that nobody would like to pick you up. That one night after I returned the rental car, I got stuck in SFO can couldn’t find a ride. Obviously, nobody wanted to pick-up from the rental car center and I received 7 cancels in a row.

Then finally, this one driver accepted my ride. He had to drive 10 minutes to pick me up. Then I realized why — many pick-ups from rental car center may end up with a drop off at the terminal or long term parking, and with time en-route longer than the actual paid trip, no wonder drivers loathe such pick-ups.

With a strong accent, he was polite and the way he sat in the car reminds me of a professional chauffeur. Then we engaged in a conversation. He told me he has been driving Uber for 5 years now, every day from noon to 4–5 am; he immigrated from Pakistan after his parents; he used to commute 2 hours one way to drive in the San Francisco Bay area. To save cost he moved much closer and shares an apartment with several others.

“So instead of $400 and commute for 2 hours one way, now it’s $700 for 30 minutes. My landlord is a Chinese lady and she’s very nice to me.”

When I asked him how he felt about the States and his home town, he replied:

“It’s nice here. I don’t live with my parents and sometimes I miss my friends from the village in Pakistan. I have a better life here but I felt very lonely”.

So he follows a very military-like routine. He drove 7 days a week, all year long. I asked him what he would like to do in the future.

“I don’t know. I have to pay for my medicine, you know, they are expensive, and other bills. Then I can save some money. I guess I will just be driving until I figure something out.”

To some extent my future is similar. The world is very uncertain. Ten years ago, I could not have predicted where I would be doing today, and I can’t forecast the next 10 years either. We will just have to figure out as we drive.

Right before I arrived home, he made a wrong turn. Then he apologized and stopped the trip early. “I made a wrong turn, and this trip will take five extra minutes. So I won’t charge you for the last couple of miles.” I looked into my APP — it was upfront fare, the trip wasn’t charged by distance like taxi anymore. He probably doesn’t understand. I opened my mouth trying to explain, but then I looked at him in the rearview mirror and genuine looks in his eyes. I paused there, and simply said Thanks - you have a kind heart.

The Lonely Soul

One evening after watching a movie, my wife decided to take Uber home as it got chilly. Nothing unusual at first glance. The driver was a young white male in a sweatshirt, like those you meet every day in a San Francisco coffee shop. I thought he was a student working some parttime after school.

My wife and I were still carried away by the movie, so we continued our discussions. The driver was very quiet, and I could tell he was listening. So to break the awkwardness, I asked the driver about himself, and it was a surprise.

“I am a software engineer, working remotely for a company not in the bay area.” It turned out that what he does during the day is not too much different from my day to day work.

But the difference is he’s just by himself. He lives in a studio apartment, and he’s the only employee in this area though there are plans to scale up at some point. He works on eastern time, so his day starts at 6 am. By three pm his workday is done. He doesn’t know anyone here, he’s an introvert and there’s still a lot of daylight ahead of him.

Therefore, driving Uber and listening to riders chat becomes his social life. He occasionally talks with people like me who still do talk and don’t always glue their faces to smart devices.

“I feel I live in a desert”. He said without any expressions on his face. “I live in this box and my existence is only reflected by the codes I write by the day. Driving like this makes me feel I am alive.”

I asked him why not work for some of the big techs there. He said he tried, but he’s always very nervous in interviews. This company was located in somewhere hard to recruit talent. He also didn’t negotiate much in compensation thus driving Uber is like his secondary income to survival. He’s eager to join a crowd to know more people, but he’s very afraid.

“Aren’t we all the same,” I said to myself. With millions of people passing by, there are only a few we look in the eyes.

Fast and Furious

Some folks drive for money. Some folks drive for connections. Some folks drive for entertainment.

There’s onetime, I requested an Uber. It should be a Prius, the official Uber stallion. But what showed up, was a fully customed Subaru WRX STI limited. The Asian driver was wearing a helmet and gloves. He has decals all over his car, even from the famous Initial D. The car stopped in front of me and my jaw dropped.

He invited me to jump in. I am sure this ride’s 0–60 is under 5 seconds. I am also sure in San Francisco this beast’s MPG should be under 12 in rush hours.

“But Why?”. I asked this question in my mind. And the driver said:

“You asked the question in your mind. Why I am doing this? I am going to move to LA to start a new job next week. I am packing up, just want to enjoy the last bit of San Francisco. I drove Uber occasionally, now I just want to take my other car out for a spin. It’s entertaining to see how riders react to this car, that disbelief — priceless.”

It’s almost comical to sit in a race-track ready car, strapped in a professional race seat, and going at 10 mph. I don’t think the driver ever passed the third gear. The engine sounded nice though. I am a fan of the mild side of Subaru and we had a good conversation about Forrester and Outbacks. I made home in one piece, and as I opened the door, I said: “Dear, you can’t believe how I got back home today …”

You never know what’s the other car parking in the Uber driver’s garage.

The Russian Just Wanted To be Heard

This happened to a recent trip in LA. The driver picked me up and for the beginning of the trip he seems to be in a good mood. He had a new car, and he asked me what type of music I would enjoy. Then we chatted about our lives, and then I told him I used to work for Uber. Then he started to rant about his unfair treatments.

“You know bro, I just wonder why Uber and Lyft never trusted the drivers! They always believed the rider side of the story!”

He went on to talk about how he encountered drunk riders that trashed his car, how riders argued about he was not following navigation, when the navigation was apparently buggy. He complained about pick ups happened in an area with poor reception but he wasn’t paid correctly. He told me that he couldn’t stop riders smoking, but then got complained by the next rider that his car smelt bad. He told me he was angry that one passenger slammed his car’s door into a post, and ride sharing company refused to reimburse his repairs.

“They wouldn’t even allow me to complain anymore. They told me if I message them again they would cancel my account. I mean, I just want to work. Why they don’t listen to the drivers?”

He was working for both Uber and Lyft, and I am not sure what he meant by they.

I understood this is only his one side of the story, but there should be a certain degree of truth in there. As I listen to his rant in the LA traffic, I begin to get a peek into his day-to-day, hectic life. The physical world is so much more complicated than the data that is captured in APP. Every Uber ride, Amazon Delivery, Postmate Order, Airbnb Stay, is so much more than a few numbers; such complex physical world interactions and human emotions are difficult to quantify. The risk of tech is that so many impactful decisions are made from distillation of the physical world without fully understanding it. Then here we are — in a world that made incredibly connected and convenient by tech, yet disinterested and polarized at the same time. Maybe all we need, is to have a long conversation, like good old times.

The purpose of this writing is to record a bit of the rider experience while I was working at Uber. My most trips were pleasant, and occasionally gave me some memorable meanings like those above. Working in tech, I feel it’s important to remind us of what we build things for, and how these innovations may change people’s lives, for better or worse. At the end of the day, what we want fundamentally, are not that different — connections, empathy, and respect.

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