If You Can Pass The 'Uber Test,' You're More Likely To Become Successful

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How To Be Successful By Talking To Your Uber Drivers

“I’d rather die than have a conversation with an Uber Driver,” said the guy in front of me to his girlfriend. She nodded her agreement as they both looked down the street for their Uber to pick them up at Philadelphia’s 30th street station. I tried to hold back a laugh and waited for my own Uber to arrive.

What the...?

Look, I totally get it. Sometimes you have those days where you don’t feel like talking to anyone. Maybe you are more introverted and ‘those days’ are most days. I’ve had plenty of Uber rides after a long week on the road where I want nothing more than to sit in the back and fall asleep. I also sometimes use the time to call my mom, if we’re being honest.

But if you tell me how much time you spend talking to your Uber driver, I’ll tell you how likely you are to be successful. And I can guarantee that dude in front of me in Philadelphia won’t be successful.

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Same with these peoplethesethesethesethese, and about a million other examples online. They all fail the ‘Uber Test.’

Learning from others is one of the best ways to grow as a person.

We know the value of talking to other people. It’s kind of a no-brainer that talking with someone else is a great way to learn, especially if that person is different than you. Sam Altman, the likely California billionaire running Y Combinator understood that when he went to talk to Trump supporters after the 2016 election. He didn’t understand and wanted to learn in order to grow as a person. Personal development is key; it’s why our first post talked about it.

That’s not me making a political statement, by the way. It’s more pointing out an example of how billionaires learn by talking from those who are different. They test their products by talking to customers, chat with people who agree with them, and actively look for those who disagree with them. In short, everyone different than them.

It’s not really a big secret though that talking to people different than us is a powerful way to learn. So why don’t more people talk with those who are different than them? Two reasons: one is fear, one is conflict.


For fear, most people are afraid to randomly strike up a conversation with a new person. Human nature means we are all afraid of rejection. It’s why a startup like Bumble is being brilliant by facilitating a way to make friends. It’s easier to meet a friend virtually first than approach someone in a coffee shop reading the same book. And it’s why people are terrified of having to talk with someone they don’t know.


The second is conflict. As humans, our natural tendency is to be highly opinionated, conflict causing creatures. Said another way, by making a claim such as ‘Rum Raisin ice cream is the best’, I’m also saying that I disagree with others who say ‘Mint Chocolate Chip’. It’s a silly example, but think about it: for everything we say to be true, it means we are saying something else is false. And since most people don’t like conflict, the easiest way to avoid conflict is to avoid a conversation with someone new. It increases the chances the other might like Mint Chocolate Chip ice cream.

If only there was a way to have 1 on 1 time with someone who is likely different than us, without any fear of approaching them, and no way to avoid the conversation…..

For example, I live in Chicago, which has 77 different neighborhoods. In other words, there is a 76/77, or nearly a 99% chance an Uber driver will be from a different neighborhood in Chicago than me. That’s a different perspective to learn from right off the bat!

Since the traffic sucks here, there’s an even higher chance we’ll have a fair amount of time to chat as well. Imagine the stuff you can learn while chatting.

Or, the New York Times says that 9 out of 10 Uber drivers are immigrants. While I’m clearly Irish, my family immigrated to the US nearly a hundred years ago and I personally can’t relate to the challenges of immigration. If the driver brings this particular topic up, as many have, it’s a great opportunity to learn.

The reality is, every person is different and you can learn from them all. You’ll never know all the interesting things an Uber driver can share if you aren’t willing to chat as well. They are unique positioned to know so much. In particular, Uber drivers:

  • Have access to an incredible amount of information
  • Can provide a window into the world of entrepreneurship
  • Are at the forefront of an incredible change to the world

Access to an incredible amount of information

Uber drivers are the new bartenders: they know everything. Think about it: they can see trends to where people go, and can listen to dozens of conversations a day between riders. I’m sure more than a few couples have broken up in the back of an Uber. It’s difficult to understate exactly how much a sharp driver can pick up.

Remember the 2016 Democratic National Convention? I lived in Philadelphia at the time for business school. It was an interesting ~month leading up to the convention as Uber drivers were constantly driving around some pretty important people. Every Uber I took that month, I asked what their thoughts were on the convention. One driver definitively told me that Bernie delegates were going to walk out in protest, several days before it happened. That guy literally knew about a Time magazine story before Time did. What a learning opportunity!

Another driver let slip he kept driving real estate development executives to some area of town that had long been overlooked. I love real estate so visited that place a few times & had some awesome ice cream. As a broke student, it was the best I could do to visit and enjoy the neighborhood.

A few years later, Forbes ran an article about how Fishtown is America’s Hottest New Neighborhood. That Uber driver beat Forbes to the punch by a few years…and he also bought some properties in Fishtown before anyone else knew this was happening. According to Curbed, the real estate prices in that area jumped 94% in a six-year period. I don’t know if those real estate developers ever tipped that driver, but I do know that driver doubled his money and is probably doing okay today!

Another really interesting topic is the driver’s opinion of Uber. It tends to come up a lot when talking with Uber drivers, especially whenever Uber is in the news. I won’t tell you what most say about Uber as encouragement to talk to your own drivers about it.

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Entrepreneurial Spirit

The cool thing is that an Uber driver is effectively an entrepreneur. They join a competitive market, by themselves, in an attempt to create a profitable endeavor. The best are entrepreneurs: they know exactly work for themselves and are quite successful at it.

The trick is they often know how to cut through what info matters and what doesn’t. For example, I had an Uber driver in Chicago who was excited for that Saturday night. There was a Chicago Bulls game and a concert going on. But which would be the right place to go for a ride?

This Uber driver did the math: he knew how many people had attended the last Bulls game, then adjusted projected attendance down because he had seen ticket prices fall on StubHub.

The concert was more difficult. The group hadn’t played in Chicago in a while, but they had new music out and all their shows on tour had been sold out. That’s a tough decision to make. But the driver’s process is what’s interesting here. He:

  • Found out what the two largest events of the night would be (Bulls & concert)
  • Found ways to research likely attendance (Stubhub & concerts in other cities)
  • Weighed upside (concert selling out and likely more rides) with downside risk (concert had more ‘boom or bust’ possibility)

If there isn’t a lesson in resourcefulness and risk-taking here, I don’t know where else you can find it! That Uber driver is the kind of person I want to learn from!

Forefront of incredible change: self-driving cars

What have been the inventions that change the course of the history of the world? Some that come to mind include:

  • The Wheel
  • Cuneiform
  • Ship Sails
  • The Printing press
  • The Steam Engine
  • The Internet (although those who know me would know I’d actually argue for the GPS system instead…Pinpoint is a great book)

However, I’d argue that the self-driving car will cause a bigger change in the world than all of them. Even if just ends up on the list, imagine the impact that will be felt by a self-driving car! It will change how we work, where we live, our social patterns, everything!

Uber’s entire business model relies on the fact that self-driving cars will be created sooner rather than later.

Let’s think about that. Uber drivers are literally in an industry that is about to change, while their own company tries to invent the technology to replace them. One can only imagine the strong emotion that is caused by working for a company trying to replace you. It’s the subject of countless movies, although this time, it’s real.

You can’t ask Hannibal what he thought about while crossing the alps, or Joan of Arc when she walked to the stake, but you can ask an Uber driver to share what their thoughts are about self-driving cars.

It’s a question that I’ve asked many times to many drivers. Some are dismissive of the concept of cars driving, while some are expecting the technology to be ready tomorrow.

The common thread through all of the conversations though is that Uber drivers repeatedly have more thoughtful, insightful comments than any talking head I’ve seen discuss the topic.

The reality too is that big, paradigm-shifting type technological change is not that common. I threw out a list up there of ~5 such inventions in the ~200,000 years of human history. Even if that rate of a huge typical change every 40,000 years is dropped down to only 400 years, we will all still be very dead the next time a huge change comes around.

So get asking how Uber drivers think about a change like this! I’d be willing to bet a book will be written in a couple hundred years on this exact topic, and some future writer would kill for your opportunity to interview Uber drivers.

So what to talk to an Uber driver about?

Okay, so you’ve decided to give talking with your Uber driver a shot! Congrats!! You can do it!! So, what do you talk about? Honestly, the best place to start is with whatever you find interesting. Talk about topics you are familiar with and have an opinion on.

Remember, the magic of Uber drivers is that they are going to be different than you & have a different perspective than you. Take advantage of that opportunity to learn a new way of looking at something you already feel the passion for. Start the conversation by asking the driver what they think about “insert subject you love here”

Or, use a generic, but non-cliched conversation starter. A personal favorite of mine is: “What are you excited about this week?” Similar to the above, you’re guaranteed to have a conversation about something that one of you find interesting. The only difference is above you are talking about your passion, and here you are talking about their's.

Pass the Uber Test

This whole article started by sharing a story of some couple that was standing in line ahead of me. They failed the ‘Uber test’. Is it an official test? Nope! But if I were a betting man, I’d wager neither of them will have a very successful life if they don’t take the opportunity to learn from others.

So set the goal of talking with one new Uber driver a month. Sounds reasonable, right? Only one per month?

With just one monthly conversation, you are learning a new perspective and opinion. You’d pass the Uber test, because you are interested in other people and learning more yourself.

And if I had to bet on someone to succeed, I’d bet on you. I’d bet on the person who passes the Uber test.

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Sean O'Dowd is a graduate of the Wharton School of Business, award-winning instructor, current consultant, and editor at Ten Minute MBA. Read more of his writing on Medium.

This article was originally published at Ten Minute MBA. Reprinted with permission from the author.