Ride-Share Roulette: The Mystery of the Unpredictable Pickup


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I remember taxis. Actual taxis, painted brilliant yellow and drivers who sat high upon their perches like gracious tyrants over this kingdom they ruled. You could whistle for them.

They’d whistle back and shuffle right over to you.

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They weren’t perfect and were hardly close to it, but they were tryinс hard to not be and that was enough to make them perfect for me. Then change happened.

Enter the apps who would share rides and promise you they’d change transportation as you knew it. You wouldn’t have to pace sidewalks in the rain waiting for your ride. You wouldn’t have to anxiously sprint towards the right amount of change because all you needed was a way to go home.

Now you simply push a button and presto, poof! Magic. A car conjures itself right to you.

Magic is what we’ll call it in marketing. Pushes your imagination further than we’re willing to discuss here. These lofty exaggerations can only come from “the type of imagined future that can only be cultivated from a tremendous surplus of venture money.”

They get to pick and choose wherever they please the privilege of creating arbitrary limits of service because there’s no payment involved to wear a medallion.

I like to call that address taxi roulette because it encapsulates the sheer gamble of: “Where the only thing you know for certain is that the rules will change day to day and the house will win.” Last Thursday I had an appointment on the other side of town. I strolled up to my appointment late with white flags already waving in both hands. I was ready to accept new levels of suffering.

This appointment was to discuss things that could have very easily been handled over email that I could’ve received up north where civilization is actually a thing. Feeling generous, I opened my ride-share app thirty minutes before my window of forty-five and thought, “Should have plenty of time.”

My phone buzzed that “your driver will be there in 3 minutes.” I scanned the area for three minutes and realized that every second I had been right on time was lied to me beforehand. Throwing on my jacket, I gathered my belongings and began walking briskly towards the curb to wait for my car.

Yeah, I’m here one of those people who just stands around waiting for the ride to pick me up. Three minutes passed, how a second does when you’re watching time try to rhyme excuses with itself. Three became five.

I glances at the clock and realized 10 minutes have passed me by. Looking at my app I watched my driver, Joshua tour around my entire neighborhood. His prison?

Traffic laws. He was lost in a man-made desert of if statements and terrible programming. Lets just say everything about how he drove around my town, imprisoned by WiFi completely laughed in the face of every rule that life tried to teach him.

I tried calling Joshua directly, no answer. Smart guy turned off his phone. I sent him a text thinking I’d at least get a text back from him through the convenience of technology, ride-share silenced.

Even respond a split second after me, looping around the same block devoid of empathy. It’s like feeding a shark that hasn’t eaten another human in years. Minutes later my app loaded up and a notification popped up: “Your driver is two minutes away.”

The ‘ride-share hopeful’ is always an optimist.

I straightened my posture in the passenger seat and looked down the street one last time hoping I could spot the corner I would have to head down in order to arrive at my destination. Two minutes. And still no Joshua.

“We are currently having trouble connecting you to Joshua” yep, no dear. What ride-share excels at isilding hope, let down after you accept its beautifully worded apology. Another message came through “Joshua had to cancel.

Connecting you to another driver…”

Y’all know I gave him too many chances to return the call, let alone apologize to me over the phone. Instead he ended up telling me something no human should have to hear. Let alone myself.

There would be no goodbye, not even a courtesy call from him. Ah yes Joshua, welcome to the business of riding-shares. “Eta is 8 minutes.” EIGHT MINUTES.

Jest you wait!! My meeting could be over by the time I arrived, all because Joshua couldn’t seem to navigate the simplest of Google Maps and my “replacement” was clearly coming from across town. You know folks, here’s ride-share roulette’s most crucial rule: The ETA is never an estimate – it’s hopef ul.

It simultaneously gives you too little time and too much time. Please think of Schrodinger’s ETA. Sure enough, my new ride, Melissa pulled up.

She was late by an additional 8 minutes on top of her new ETA. Which brings me to at least 28 minutes spent waiting. When I first requested my ride, I was told 3 minutes.

“Sorry for the wait” was the first words out of Melissa’s mouth as I hopped into her immaculate vehicle. “The app dropped me off at the wrong location initially.”

I empathized with her. Melissa was a victim to this as well.

She wasn’t the one who programmed this into insanity. She was another cog in the machine. Trapped together by algorithms that seemed to have no other purpose than to break you mentally.

Drivers are victims too. Many times drivers are the fall guys of the ride-share roulette. They’re people like you and me trying to make a living in the gig economy, victims to technology that we, let’s be real, ruined in an attempt to navigate us through the easiest rides of our lives.

Sure, go complain to the tech bros pulling in millions, not your ride driver. Melissa drove the routes I wouldn’t have normally taken. She wouldn’t deviate.

I could tell that she literally believed the app was leading her right. Hell, she must of programmed it herself because through gridlocked construction I could see this undeniable anguish that she was being routed through a damn maze. “It’ll be faster this way,” – the app says.

I caught a glimpse of Melissa in my rearview and I could see from her uneven eyebrow that she wanted me to be impressed. Melissa didn’t have an eyebrow. Neither did I.

The algorithm. For real, the algorithm. The silent bystander turning our rides against each other while having some godly understanding of the maps we drive on that no regular person knows because they’ve actually drove through these streets for years.

Rule two of ride-share roulette: Drivers trust the fuck out of the app. Whether the app is right or not, the driver will argue so until you infinitely question them both. It can send you down streets that don’t even exist anymore because that one highway isn’t being constructed or during these times isn’t safe to pass through.

How is the app going to get us to point A if we can’t? Because if the app can’t get us to our pickup location, what makes us think they know our best route to any other location. I walked into my meeting 17 minutes late causing me to awkwardly shift in my seat while apologizing every DIY abs climber nods their head in empathy at.

I looked a wreck, flushed from running back inside after what felt like my soul had just been beat out of me in minutes. My coworkers looked at me with pity. Poor souls, I could tell that they’ve rode-share rolled before.

It’s sad how you not only come to terms with losing money and hours of your life to a process that is inefficiency, but it’s completely unreliable. We, the people have allowed this process to be integrated into the foundation of how we function daily. Allow yourself to be screwed over time and time again for the privilege of living our lives through a screen.

Ride-share and their cars are the epitome of what technology was supposed to be. But allow me to take a wild guess. You get variable outcomes when riding.

Some days where you hit the ride-share jackpot and it makes you forget about all the terrible rides you’ve previously encountered. Every ride you take comes with potential consequences. Good rides are clean vehicles and respectful drivers.

Bad rides consist of…. Horrible cars. Remember that scene in Pulp Fiction where Mr.

Wolf told Marvin he should have just taken an Uber? Yeah. And overly aggressive drivers who feel like they can sell you their life story along with you just getting home.

If I remember correctly, Mr. Wolf was in a world just like ours but well let’s just say it’s dystopian and the foundation of society is based off of robots getting paid to wage war with eachother, but can’t seem to give you…service that you reasonably expect. Similar to surge pricing that feeds off of our desperation – as a general idea- to ravage your wallet.

Let’s say you’re trying to order a car late at night, get ready to pay 2-3 times your normal fee. Because once the app recognizes you’re willing to pay just about anything, they know you’ve surrendered all logical value you have to spend. Rainy nights coming home from work?

That base price? Forget about it. Now your price triples because the help you thought you were signing up for is now holding hostage your last stop until you accept the fare.

No promise is too extreme when your mind is preoccupied with the abuse of your pockets. Trust me I plan ahead of time, and fell right into that exact trap. Nowadays I give every ride their time to get to me.

I’ll even search 3 or 4 different apps to ensure all their prices match up before I confirm my payment. Know which areas in my neighborhood to not get dropped off in that will more than likely complicate the algorithm- what was I trying to say? Mess with my ride and make me late to arrive at my destination to receive my fare back.

But yes, I avoid those roads like the plague now. But if there’s one day I just want a cab. I want to flag down a taxi.

Yeah your taxi will probably be dirtier, the driver probably rude, and you’ll be insecurely fishing through your pockets for exact change because you’ll need to do quick math and tip under 10%. But at least there was integrity in that transaction. Paying for a taxi meant you were accepting a no-frills, straight to the point service.

You were handing over cash to drive you very similarly to how you’d hand over cash to buy a sandwich. Although the transactions are completely different, both felt genuine. You’re making a simple agreement: take me where I need to go and I’ll pay you for your troubles.

I took an awful ride-share experience this past week. My driver couldn’t find me despite me aggressively gesturing over my target destination while standing underneath a street light. This whole experience made me yearn for the days when you could just catch a taxi off the street.

So this week I took matters into my own hands to try and make that possible. Low and behold, my car was already assigned and I was just one click away from my ride beginning. Are you serious.

My driver already picked up on my predetermined destination AND drove past my normal pick up spot. Talk about not ever mentioning the weather but we ended up making small talk. The price for my ride met all the expectations I had going into paying for the ride-share.

I felt like I had just rewound in time to where technology wasn’t at our fingertips controlling our lives with apps. PayIng cash felt so luxurious after times of only using digital forms of payment. I’m not going to sit here and say taxis are the be all, end all of our transportation issues.

Heck no they’re incredibly inefficient. You can’t always find one when you need it and people drive them rude. If I had to guess, I’d rather be accountable for a system that works this messy than another system just as messed up, but masquerades as perfect because of a sleek UI and over-promising.

Ride shares I still partake in ride-share roulette, sure but unlike others that believe there are ‘Uber-etiquette’ rules you must follow. I know it’s a part of life now and not riding is honestly more of inconvenience than just getting pumped. What I do know is that it will fail you more times than it’ll work, but at the end of the day it’s better than nothing and I believe that still.

Plus, I’m not in such a high enough position where I can afford to not use them. But I know days were I just can’t lose. Days I simply cannot afford to not get where I need to on time.

I will suck it up and order a taxi cab. Plus it’s nice to think that someone, somewhere can be trusted to at least keep the one promise: to drive you to where you need to go. My buddy and writer Evan Morgan takes this one step further and mocks this promise that taxi drivers make but can’t always keep.

When he gets into a taxi and gives his destination, he encourages his readers to think of it like this: you aren’t riding with this driver who has no plans of dropping you off at your destination. You are making him make a stop along his inevitable death cruise, or risk major turbulence. Until we as a people can properly regulate these drivers, we all have the opportunity to play the ride-share roulette we’re subjected too.

Where every click on the app is robbery..

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More times than not, the tech CEOs on the ride hoping you’ll swipe surge pricing and their “lets make life easier for everyone!” investors stay level headed and wins. We’ll all walk away with heightened heart rates, but the riders who need the ****ing jackpot are always going to lose.

It takes all it can from you while based off of complete uncertainty and four key rules. Rule one:

The pricing system. They have crafted an equation that calculates how much value you and other passengers can potentially gain from your ride or how useful this service will be for you and your peers.

Then they price you accordingly.


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