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Paying In The Future, With Humans

New ways to pay for things have been steadily eliminating the human factor in transactions. Pay With Square puts it back in, but still feels sufficiently future-y.

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One of the more interesting shifts happening right now is the way we pay for things: We got used to putting everything on credit cards; then we got used to buying things online; now we're getting to used to paying for things with our phone.

The shift has been mostly about convenience. From crumpled, messy cash to smooth, swift plastic — I barely even have to sign anymore — to nearly invisible transactions online or with our phone. A side effect is that the human interaction part of the transaction has been slowly sliding away. You have to hand cash to a cashier. More and more, you don't have to hand them a credit card. Or at an express checkout, deal with a human at all. There is no human online — really, try to talk to one at Amazon on the phone, I dare you — and the tap-your-phone payment systems reduce that further from cards, since there's no chance you'll have to sign a receipt (though you might have an awkward conversation about using your phone to pay).

So what's interesting about Pay With Square — Square's new way to use the service for consumers — is that it puts the human part back in. When it works, you walk into a store, turn on the app and then when it's time to pay, you tell the cashier to put it on your tab, using your name. You have to talk to them and tell them your name and hey, you might actually have conversation. Though it might be about how your name isn't on the roll because you didn't open the app soon enough, and hold on one second, oh let's just give it another minute, aha there are you are, oh technology LOL. So you talk to somebody, but you don't lose any of the convenience factor: You don't pull out a card, you don't tap your phone, you just open the app and say your name.

The problem is that the process of setting it up is somewhat cumbersome — you've gotta go to a place, make sure it's using Pay With Square (and only a fraction of business that use Square at all use Pay With Square), add the card to your wallet, and remember to open the app to open your tab. You've really gotta be intent on using Pay With Square. And oddly, for nailing the human component so well, one of the problems I've had with the previous incarnation of the service, Card Case, is that I couldn't leave a tip like half of the time because the notification didn't work right and I didn't see that until after the fact. So, the next time I'm in Cafe Grumpy I need to drop a fiver in the bowl.

All in all, though, there is something really pleasant about the payment experience with Pay With Square, more than some of the other services I've used, like Venmo (which I like for interpersonal transactions) or some of the others coming to market, like PayPal (which is how Satan takes payments, I'm sure).

Sometimes talking to other people isn't so bad, you know?