Why I’m No Longer Willing To Drive For Uber

Surging Everywhere But Where I Am Uber

In part one of this two part series, we discussed seven reasons why everybody should work a minimum wage job at least twice in their lives – once during school, and again after they’ve made a comfortable sum of money.

The reasons cited are:
* Develop a stronger work ethic
* Develop better social skills
* Be a kinder, more empathetic person
* Get out of a bubble
* Make extra money and become a more disciplined spender
* Become more business savvy and entrepreneurial
* Get accustomed to life not being fair

After seven months since first testing out the platform, I’ve decided to no longer drive for Uber except to occasionally pick up someone along the way. The 10% – 20% fare cuts in January 2016 have made driving not worth it beyond the initial sign up bonus period (e.g. $300 after 20 rides in SF).

I’ve learned everything there is to know about the existing technology and I’ve already benefitted from all the additional non-monetary benefits I’ll be highlighting in this post. 


The main reason why everybody should never expect a $1M inheritance, never start off with a luxury car until they’ve gone through junkers, never manipulate their parents for more money if they are already adults, and never expect to go straight to the corner office without paying their dues is because you will grow this WARPED SENSE OF ENTITLEMENT.

Only when you see the other side will you truly appreciate what you have. Only when you struggle and suffer over time will you truly enjoy your achievements. Pity the person who was born with everything.

The following are my final takeaways from driving for Uber. It’s good to go through new experiences and then move on once your learnings are exhausted. I’ve got better things to do with my time now.

1) You learn to keep on going. I firmly believe at least half the reason why people are successful is because they never give up. In startup land, successful founders keep on pitching until someone says yes. In blogging, successful bloggers keep on writing even if they make no money for years. In tennis, winning players run down every single damn ball until their opponent’s spirits are broken.

Driving for Uber has a funny way of making you excited about your next trip and depressed at the same time. There are still a lot of kinks in the app that make driving frustrating. For example, in the featured image above, notice how I’m in a dead zone where there is no demand, even though I’m in downtown San Francisco. Meanwhile, there is surge pricing everywhere else! How frustrating! But given you can see there is demand elsewhere, you keep on going out of sheer will.

2) You learn how to eat some good ‘ol humble pie. Growing up in Asia for the first 14 years of my life taught me the importance of humility. Unfortunately, when I came to the U.S. for high school, I began to grow a pretty big ego to the point where I was probably perceived as a pompous jackass by a number of folks. Joining a prestigious private firm in Manhattan only served to inflate my ego further. It was only after 9/11 that I decided to make a conscious effort to start being more humble. I took up Stealth Wealth and pretended not to know a lot of things in order to not come across as a know-it-all.

There is something extremely humbling about having the financial means to leave Corporate America for good, yet be treated as someone who may be struggling to just get by. I picked up a couple of tipsy 24-year-olds who were renting an apartment not too far from where I currently live. They thanked me for being someone who helped save them from a DUI. It felt nice helping an elderly woman with her luggage. After I helped her get out of Rhino, she handed me my first ever cash tip of five $1 bills! It was a proud moment, yet incredibly humbling at the same time.

3) You’ll learn how to better control your emotions. Anybody who’s ever driven has experienced some degree of road rage at one point in time. I know I’ve shouted at someone for cutting me off and felt a tremendous amount of annoyance when a Porsche 911 drives 10mph below the speed limit in the left lane! Some people get so pissed on the road that the’ll hunt you down and hurt you if you don’t apologize profusely. Some might even try and kill you.

There will inevitably be times when you’re working and some driver will do something that will tick you off. But since you have passengers in your car, and don’t want a poor rating, you learn how to control your emotions by staying calm. You learn to let things go in a monk-like manner.

4) You’ll learn to accept and LAUGH at your misfortune. Half the battle in succeeding at anything is to just survive long enough. I see so many people quit before momentum really begins: at their jobs, learning a new song, blogging, trying to get better at a sport, selling too soon, etc. If only more people just persevered, they’d see greater rewards.

Long Uber Ride

Long Uber ride to Vallejo from SF starting at 10:30pm when all I wanted to do was go home

For example, it was 10:30pm and I had just finished driving for 1.5 hours after a fintech meetup downtown that went from 6pm – 9:00pm. I was tired, but not too tired to drive! I was on the east side of the city, hoping to catch a fare to make money going west back home. There was an 80% chance that such a ride would occur based on my analysis of my previous 100 trips.

When I went to pick up what I thought would be my final passenger, I saw a middle age woman with a piece of luggage. Oh great, we’re going to the airport, I thought to myself. The airport is 16 miles south of San Francisco and not my home’s direction. Usually I wouldn’t mind a $32-$36 fare, but it was late. Well, instead of going to the airport, the lady put in the city of Vallejo, 35 miles north and across the bay! Holy crap! With no traffic, it still takes 35 minutes to get there. The real bummer is that there would unlikely be any fare back. My “last passenger” ended up making me work another 1.5 hours until midnight because I did end up finding a couple passengers out in the boondocks. Luckily, the Vallejo trip was a 1.4X surge price that came out to $80.66.

Yes, driving for Uber will test your endurance. It’s dangerous to drive too tired, so definitely don’t do that. But my experience driving has given me added energy to work longer online and endure longer on the tennis court. Thankfully, Uber developed a new feature where drivers can input the destination they want to go for their final ride to potentially pick up a rider going your same desired direction.

5) You’ll learn how to deal with difficult situations. Although you can make roughly 15% more picking up UberPool passengers, the rides are usually less fun because you converse less, and there’s a bigger chance for something to go wrong. One evening I picked up one woman at her pricey Pacific Heights apartment. As I began going a different way from her route in order to pick up the other passenger she said frustratingly, “What are you doing? My destination is the other way.

Then I asked her, “Sorry, but I’m just going to pick up another UberPool passenger. You did request an UberPool didn’t you?

She said she did, and kept quiet unhappily. I was annoyed that she was annoyed at me picking someone else up. If she didn’t want to share the car, then she should have requested UberX and paid up! It’s not that much more expensive.

When I got to the other passenger’s destination, the woman wasn’t there. I waited there for a couple minutes out of courtesy until my Pacific Heights passenger said, “You know, we are wasting time sitting here. You can call her you know?

Yes, I know I can call, but calling people can also annoy the receiver. After another minute, I did call the missing passenger and it went straight to voice mail. All this time I’m thinking, great, my current passenger is unhappy and she’ll be giving me less than a 5-star rating.

My current passenger then said, “It’s been several minutes now. You should cancel.” Given I dislike people who are late, I acquiesced and cancelled.

As I was pulling away from the second passenger’s apartment, I saw her finally run out and wave me down. I stopped, and apologized that since I had cancelled, I could not take her. Then she got pissed and told me “This is terrible customer service.” Then I told her a simple solution is to just request another UberPool and we can get going.

She fumbled around and told me she couldn’t figure out how to do it. I wasn’t about to get out of the car, teach her how to use the app, and make my existing passenger even madder. I apologized, told her I’m sure another car will arrive shortly, and drove away.

What I really wanted to tell her was, You idiot. First you come out five minutes late after already getting a four minute heads up that I was coming after requesting a UberPool ride. Why are you so inconsiderate to me and your fellow passenger? Then you don’t know how to press the UberPool request button on your app that you just requested? Then you lie to me and tell me you’ve been standing there in the lobby waiting for minutes already when I was clearly right outside your lobby. Hope you never get another ride!

But of course, I kept my cool, apologized and wished her the best of luck.

Lesson learned: Cheaper customers can cause more trouble. It’s weird how they complain much more than UberX customers. I’d much rather focus on higher end customer who better appreciate the service and product. This is one of the reasons that compelled me to raise the price of my freedom book on severance negotiations by 50%+ after I added 50 more pages of insights. So far, there’s been an increase in demand.

Taxis Hate Uber

The Taxi driver who spit on Rhino

6) You may understand what it’s like to be hated on. As a minority, getting hated on is a pretty normal occurrence in America. You just kind of learn to live with the insults or slights. But until you are in someone else’s shoes, you’ll never know what it’s truly like.

After dropping off a passenger in congested Union Square, I got stuck in traffic on the way back. As I was inching my way forward, a Yellow Cab driver suddenly tried to jut right in. But given traffic wasn’t moving, I was stuck, and he got pissed off that I didn’t make way. As his lane started opening up, he drove by Rhino and spat on his hood!

Yes, taxi drivers hate Uber drivers even though they can drive for Uber if they want. You’re seeing riots in France against Uber drivers for example. There are plenty of other areas of the country and world where the anti-Uber sentiment is real. If you have never experienced hate and discrimination, being an Uber driver can help you gain a tremendous amount of perspective.

7) You’ll see through all the sales and marketing voodoo. Uber upgrades its app a couple times a month. With a recent upgrade, they’ve implemented FOMO messaging to get you to try and drive more. For example, one says, “You’re only $9 away from making $20! Keep driving” Another message says, “There’s so much money out there to be made!” That is some smart marketing by the folks at HQ.

Fake 4.5X surge pricing to convince you to keep driving. Bullshit!

Fake 4.5X surge pricing to convince you to keep driving. Bullshit!

But here’s my favorite sales bullshit message I got that is clearly NOT TRUE. Now, whenever you click “Go Offline” the app will often tell you there’s a huge surge pricing going on, even though there’s no surge in your location. They’ll choose a location that’s 30 miles away and make you believe you can get that surge price, even though the surge will likely disappear if you ever are not savvy enough to chase the surge! Never chase the surge.

A lot of money is lost by buying things you don’t understand or need. Being able to see through misleading sales and marketing is a skill that may protect your fortune. You will not become one of those poor older folks getting scammed by nefarious con artists! And if you want to learn how to make more money, you might as well follow the marketing tips of the most funded startup in history.

8) You’ll motivate others to work hard. Motivation is something I always seek because life is pretty easy in America compared to many other countries. We’ve got good public infrastructure, abundant water, cheap food, and government programs to help us out when we’re down and out. As a result, I think many of us, including myself, take our comfortable lives for granted. We get out of shape, learn to speak only one language, and don’t take advantage of all our opportunities.

One personal finance client I’ve been coaching for the past three years told me his teenage son is completely ungrateful. He doesn’t do any chores, nor does he take on any summer jobs to make extra money. He doesn’t do any volunteer work either, and would rather spend his time on the computer or hanging out with friends.  Of course, he expects to go to private university on his parent’s dime because that’s what all his graduating classmates are doing. My client is worth several million dollars.

No matter how hard the father tried to encourage his son to do some work after school, he would not. If dad’s not working hard after work, then why should I? was his attitude. At age 50, my client has a right to relax at home after 10 hours in the office since he’s providing a good life for his family. But because this father cared so much about not spoiling his son, we came up with a plan for the father to sign up for Uber and make at least 20 trips to collect the sign up bonus in order to inspire the son to do more.

Where are you going dad?” asked the son at 9pm one evening.

I’m off to do some driving in order to make enough to pay for groceries this month son,” replied my client.

After my client got back around midnight, he found his son waiting for him in the living room. They had a nice long talk about the importance of work ethic. The very next day, the son decided to get a minimum wage job helping teach kids how to swim. It was a start!


If you can build strong character, I’m confident money will eventually come. Strong character means being thankful for what you have and never failing due to a lack of effort. The feeling of entitlement goes out the window once you know what it’s like to work hard for little money for an extended period of time. You will never forget where you came from, and as a result, you will go on to lead a much more gratifying life.

Driving for Uber is hard because it requires mental focus and physical activity. With further rate cuts, staying motivated to drive has become impossibly difficult. Uber says that rate cuts will spur demand. Uber has even offered minimum guaranteed hourly incomes if you promise to pick up X amount of riders for Y amount of hours. The subsidies are unfortunately not enough because they are temporary band-aides that try and stop the structural decline in fares completely controlled by headquarters.

When drivers see their paychecks decline, yet hear Uber raise another round of funding at a new record high valuation of $69B, that’s not OK. It’s not OK because none of that windfall goes to the very drivers that make Uber so valuable. Further, the company has some corporate cultural issues with the treatment of women. Travis Kalanick, the CEO finally stepped down in June 2021 due to all the problems within the firm.

When you add up the cost of your time, gas, maintenance, and insurance (goodness forbid you ever get in an accident), driving for Uber long term is probably not the best use of your time. To be fully protected, you need ridesharing insurance coverage that may cost anywhere from $150-$350 a month extra, further eating into your profits, and further making driving not worth it for the casual driver after the sign up bonus.

Updated for 2021 and beyond. Uber finally has gone public.

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