The Apple Pay Challenge: Lessons Learned From My Week Without A Wallet

It’s not without its glitches–and its enemies. But Apple’s mobile payment system still feels like the future.

The Apple Pay Challenge: Lessons Learned From My Week Without A Wallet
[Photo: courtesy of Apple]

A week ago, when Apple’s Apple Pay service became available for the new iPhone 6 and 6 Plus, I decided to give it the most real-world test possible, by leaving my wallet at home and paying for a week’s worth of stuff using only Apple Pay. Along the way, I wrote an initial post explaining the experiment and a midweek update.


The experiment ended on Monday, when I opened my sock drawer, retrieved my wallet, and ceremonially returned it to my pocket. Here’s a final report on my week with Apple Pay, and what I learned:

The quality of the Apple Pay experience varies.

My experiment was a success in that there was never an instance when I theoretically should have been able to use Apple Pay, but couldn’t. And I never buckled and paid for anything with a card or cash. There were times, however, when Apple Pay felt like a needless complication, not a great leap forward.

Oftentimes, the technology was buttery smooth–especially at my local Whole Foods, where the transactions happened so quickly that it did feel a little like wizardry. But when I tried using Apple Pay at a McDonald’s drive-thru, it was so unwieldy that I felt guilty about holding up the hungry motorists behind me.

In principle, the cashier was supposed to be able to hand me a portable terminal so I could do the Apple Pay gesture in my car. Instead, he took the phone from me, then handed it back and asked me to launch Passbook. That’s an unnecessary step: The app pops up automatically when the phone nears the terminal. And then he had to hand it back twice more before the payment went through. (Fortunately, neither of us dropped my phone.)

Inside the same McDonald’s at the counter, my iPhone 6 kept asking me to hold it closer to the payment terminal–even when I was pressing it up right against the sensor. Eventually, it worked, but if I’d had a credit card or a $5 bill with me, I would have given up on Apple Pay after the first error message.

Why my experience was inconsistent from store to store, I’m not sure. It might have something to do with the brand of payment terminal in use, or the cashier’s familiarity with the process, or how deftly I held the phone and performed Touch ID authentication, or general kinks in the system. Or maybe a little bit of all of the above.


There’s not a lot of margin for error.

Apple Pay competes with using credit and debit cards the old-fashioned way, by removing one from your billfold and swiping it. And plastic is actually a pretty great way to pay for stuff: It’s simple, quick, and reliable.

At its best, Apple Pay is better still, and more secure. (The store’s payment system sees only a one-time transaction code for your purchase, not full details of your credit card.) But in any scenario in which Apple Pay works less than flawlessly–whether because of technical glitches, confused cashiers, or user error–it loses most of its advantage over doing a card swipe. If it turned out to be as clunky as I found it to be at my nearby McDonald’s over the long haul, there wouldn’t be any point in using it.

You need to be sure whether you can use Apple Pay or not.

The only retailer I visited during Apple Pay’s first week that was making an obvious effort to drum up interest in the service was Whole Foods. There was signage promoting the service at every checkout aisle, and it was even mentioned on the payment terminal’s screen. Other stores I visited weren’t yet playing it up–including the Apple Store itself.

Me, paying for lunch at Whole Foods–swiftly and painlessly–with Apple Pay Photo: Daniel Terdiman

Even if a chain is on Apple’s list of official partners, it’s not a given that you’ll always be able to use Apple Pay. At my local Chevron station, I successfully bought gas–once I figured out that I needed to go inside and pre-pay at the register. But when I went back to the same station later in the week and assumed I knew what to do, I discovered that the cashier was ringing me up at a different register, without a contactless terminal. (When I told her that I had no way to pay other than with my phone, an expression flashed across her face that suggested she regarded me as a crazy person, but she politely started all over at the other register.)

That’s another issue relating to the tiny window of time which Apple Pay has to be superior to swiping a card. If you have to pause and wonder if you can use Apple Pay, or be picky about which register you choose, it’s already lost its edge.

Retailers could screw this up.

In fact, CVS (where I successfully used Apple Pay several times) and Rite Aid already are doing their best to foil Apple Pay. By the end of the week, they’d disabled contactless payments altogether in order to prevent anyone from using Apple’s service at their stores.


Both druggists, along with Walmart and others, are backing a competing digital wallet app called CurrentC, which isn’t arriving until next year. It doesn’t sound like much fun: To use it, you’ve got to turn on your phone, launch an app, and scan a QRC code at the payment terminal. And CurrentC isn’t really an Apple Pay replacement, since it works with debit cards and bank accounts, not credit cards.

Apple Pay is never going to be the one digital wallet to rule them all, since it will only work on properly equipped Apple devices. But really, what retailers should be doing is welcoming a variety of payment options–not shutting some of them out even though the stores’ registers are technically capable of accepting them. The odds seem far higher that CVS and Rite Aid will eventually decide to accept Apple Pay than that consumers will flock to CurrentC.

I’m still cautiously upbeat.

I cheerfully admit that I’m happy to have my wallet back. More than once during the week, I was in a store and realized at the very last moment that I’d forgotten that I could only shop at Apple Pay-friendly establishments. (I even asked my wife if she’d like me to buy her popcorn at a movie theater, and then had to sheepishly retract the offer.)

But even though my experience with Apple Pay wasn’t perfect, and despite obstacles such as recalcitrant retailers, I had a good time using it. I expect to reach for my phone rather than my billfold quite often from now on–partly for convenience’s sake, and partly for the privacy and security benefits of being able to pay a store without sharing any information about myself. And if mobile payments finally start to catch on–which seems likely to me–we could end up looking back on last week as the most important moment so far in the history of the technology.

About the author

Harry McCracken is the technology editor for Fast Company, based in San Francisco. In past lives, he was editor at large for Time magazine, founder and editor of Technologizer, and editor of PC World.