Your fear of rejection is all that’s keeping you from getting a better deal on grapes.

Fruit guy clocks me right as I step out of the station. "Amazing grapes today," he says. "Very special." 

I reach for the bag and with a practiced hand commence my inspection. These grapes are fine— maybe better than fine. But that's my business. Fruit guy doesn't need to know what I think. 

"How much for the grapes?"

"Nine dollars."

I don my mask of shock and disgust and return fire with a low-ball offer of five dollars. It's okay to low-ball the fruit guy. 

Five dollars is no good, he tells me. These are very special grapes. They're so special that I need to try one. I try one. 

And the grapes are good— they're firm for fruit stand grapes and are possessed of sufficient grapey flavor. For the right price, they could be my evening grapes.

"Six dollars." I produce my money clip and start counting out the bills before he can counter— a maneuver I picked up during a sojourn in the diamond business. 

But today he isn't going for it. These are very special grapes. I try to explain that six dollars is my very special price, but I'm coming to understand that I won't be going home with these grapes at a number I can live with. Though life has taught me never to go to war with my desires, it has also taught me to walk away when the deal isn't right.

It doesn't matter anyway. There's another fruit guy down the street — a more reasonable fruit guy who isn't afraid to cut a deal. He's probably even got the same grapes. 

I know people think I'm crazy for haggling with the fruit guy, but I'm not, because grapes are expensive and I really like to eat a lot of them. To engage in the type of grape arbitrage necessary to keep me in good grapes, I have no choice but to negotiate.

Occasionally, I'm accused of shaking down the fruit guy by my less business-savvy peers, but I don't see it that way, and I doubt he does either. If anything, he probably respects me as a fellow businessman. Might we exchange a few terse words in the course of a failed transaction? Sure. But that doesn't mean we won't make a deal the next day. 

If people want to pay sticker price for grapes they can be my guest. But they're only doing that because they're afraid— afraid of their offer being rejected. 

I’m just as fearful of rejection as the next guy, but a credo remains burned indelibly into the psychic tapestry of my ego: 

There is nothing the fruit-stand guy could ever say that could hurt me. 

The scope of outcomes my grape negotiations might yield is narrow if not binary. If you understood that, maybe you too would haggle for grapes.

And once we're all on the same page about the grapes, we could test our mettle on the blueberries.