Claire McCracken

How to Buy A Round and Stop Worrying If It'll Come Back to You

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According to Dr. Richard Thaler, a Nobel Prize–winning professor from the University of Chicago who studies behavioral economics and the psychology of decision-making, the custom of round-buying should be ditched altogether. He thinks it puts an unrealistic strain on our wallets.

Right at this moment, as you contemplate the backlit, multicolored array of bottles behind the bar, and the expectant—soon-to-be-impatient—expression of the bartender, you’re inclined to agree with the good Dr. Thaler.

Moments ago, you pushed through the doors of your favorite local watering hole, found your crew, and sidled over, savoring the prospect of a well-earned post-work cocktail—only to land in a briar patch of behavioral economics and psychologically fraught decision-making.

Your pals had barely acknowledged your arrival with a chin nod or half-raised hand, but then, as they noticed you pause before setting out for the bar, their attention perked up. They sat up a little straighter, leaned forward just slightly….

There was no way out of it:

“Anyone need one?”

Everyone, it seemed—up to and including those who qualify as “colleagues” more than “friends”—did need one. Four, five, six hands shot up, and just like that, you were looking at a $50 outlay, at least, counting tax and tip.

Claire McCracken

But off you went, wallet in hand and drink orders in mind, because what else could you do? Even the knowledge that you won’t be made whole on this deal if you stay for four more rounds wasn’t enough to make you breach round-buying protocol, however tyrannical it seemed to you in that moment. So here you are, flooded with anxiety, staring at the bartender, and grasping at the wisdom of Dr. Thaler, miles away in Chicago, presumably having a quiet beverage by himself.

But maybe instead of behavioral economics you should consult a more ancient wisdom. Scrap the two-dimensional, pragmatic approach, and come to terms with the issue on a deeper, philosophical level. We take encouragement from the fact that the sages are in universal agreement on this one. From the foothills of Tibet to the cafes of Paris, and pretty much everywhere in between, they view generosity not just as a good turn, but as nothing less than a cornerstone in the edifice of human morality and civilization. A quick sampling:

“Who will be the happiest person? The one who brings happiness to others.”—Swami Satchidananda

“For it is in giving that we receive.”—Francis of Assisi

“Generosity is a mark of bravery, so all Sioux boys were taught to be generous.”—Luther Standing Bear

Those should be a start, especially that last one: Bravery! You can be brave, bellying up to the bar like this, facing your penny-pinching demons, and buying drinks for all your friends (and even some semi-friends). You are also, according to some of history’s greatest thinkers, demonstrating your merit, helping more than you realize, and embodying pureness of heart by not expecting anything in return.

“The value of a man resides in what he gives and not in what he is capable of receiving,” said Albert Einstein.

Claire McCracken

Your friends will appreciate it, and respect you, even if they don’t repay your gesture financially. “There is no act of faith more beautiful than the generosity of the very poor,” says a character in Gregory David Roberts’ novel Shantaram. You may not qualify as ‘very poor,’ but chances are, your budget can’t withstand too many $50 rounds, so, yes, you’re performing a beautiful act of faith here. You’re expressing an “inner attitude of compassion and loving-kindness,” as the Dalai Lama phrased it. You’re actually winning, as Charlie Sheen might have put it a few years ago.

You might be temporarily depriving your bank account, but you’re permanently nourishing your soul. You’re moving the needle toward the good at both the subatomic and infinite levels.

And if you prefer to stay in shallower waters, well, you could always try loosening up and focusing on having a good time, instead of, you know, accounting.

But however you get in the right frame of mind, your moment of truth has arrived: Go ahead, deliver your pals’ drink orders in the steady, unwavering voice of pure generosity—that bartender's been waiting long enough now. Maybe there’s an expensive glass of Champagne on the list, or a Long Island Iced Tea. And maybe your friends throw nickels around like manhole covers, or they’ve got alligator arms that can’t reach their pockets. You don’t care. In fact, you’re happy about it. You know that this round may—or may not—come back to you in some way, at some time. But you also know that’s not the point. The point is, instead of trying to tear down centuries-old traditions, the University of Chicago should teach a course called “Generosity Is Its Own Reward, 101.”

The more advanced, 201 class would address how to also buy an order of spinach artichoke dip for everyone without expecting anything in return, but let’s take this one step at a time.

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