Yale students Thomas Powell (left) and Manus McCaffery (right)

The assignment was simple, if not a little daunting: Walk up to a stranger with a red paperclip and convince him or her to trade it for something bigger and better. Then repeat the process with the new item.

Based on the children’s game Bigger and Better, the One Paperclip Challenge took off on the Internet in 2006, when it was the subject of a TED talk by a Canadian blogger who managed over the course of a year to trade his way up for a house. It’s also part of School of Management Professor Zoë Chance’s Mastering Influence and Persuasion course, where it’s intended to help students improve their powers of persuasiveness, while also getting used to rejection.

Students in the course were given one week to pull off as many trades as they wanted. The task isn’t easy, which is the point, says Chase, an assistant professor of marketing.

“When students experience rejection repeatedly, they build resilience,” she says. “And after getting rejected and rejected, we find students are actually more willing to take risks. They end up learning to not feel uncomfortable and self-conscious in this way that turns other people off when you’re asking them.”

At the end of the week, students presented the items they wound up with, from a glass of wine  to boxes of books to vacations, and each section of the course voted on whose item was  the biggest and best. In one section, though, there was little suspense who would win. Manus McCaffery, a second-year graduate student at the Jackson Institute, and Thomas Powell ’18 arrived in class with the keys for a 2000 Volkswagen Passat (which they plan to donate to charity). Students streamed out of Evans Hall to find the car parked in front of the building.

The pair explained that it took 10 trades to get to the car, beginning with a $5 gift card from Caseus, a local bistro. In the final trade, they swapped a painting for the car from New Haven’s Unique Auto Sales, where he spoke with sales manager Caroline Heffernan. “I told Caroline what we were doing and she immediately said yes,” says McCaffery. “There’s a good story here. Turning a paperclip into a car and giving it for a good cause, this is something everyone can get behind.”


This story originally appeared on the Yale School of Management website.