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Jia Jiang was expecting a no.

Two weeks ago, the Austin, Tex., entrepreneur asked a Krispy Kreme employee named Jackie to glaze and fuse five doughnuts together like the Olympic rings. Without hesitation, Jackie fulfilled his request, and she did it for free.

That was day three of Jiang's "100 Days of Rejection Therapy." He's aiming to get rebuffed daily for more than three months – while blogging about it, of course. "My goal is to desensitize myself from the pain of rejection and overcome my fear," the 31-year-old wrote on his website, which shows him asking a stranger for $100 and begging another to play soccer in his backyard. Results vary, but Jiang claims all of it is building his confidence. (He's also earned viral fame: Jackie's benevolence garnered more than two million views on YouTube.)

Rejection is having a moment, with experts exhorting that what doesn't kill you makes you stronger. Childhood hardship has been linked with success later in life (think Paul Tough's How Children Succeed: Grit, Curiosity, and the Hidden Power of Character), and more recently, others are arguing that adults need to toughen up with a little adversity – to succeed. In Antifragile: How to Live in a World We Don't Understand, Nassim Nicholas Taleb posits that society is split between the fragile, the robust and the "antifragile," who thrive off life's hard knocks. We should all be like them, Taleb insists. But while psychologists agree that fear of failure can paralyze our lives, they are skeptical that complete desensitization to rejection is a formula for success.

For Jiang, the daily self-dare began shortly after he lost a major investment deal in early November. "The final rejection hurt as if Santa Claus showed up in person and told me he's not real, and then ran away with my gifts," he bleated on his website.

Put off by his own vulnerability, Jiang decided to embark on his own version of "Rejection Therapy," a technique concocted by Jason Comely, a Winnipeg Web developer who experimented with daily negations to get over feeling socially crippled when he was working from home. Comely patented a game version of the technique in 2010. With the tagline, "rejection is success," it challenges players to get refused every day as a way to build strength and character. It also promises "immunization" against the irrational fears of rejection that often restrict people's lives. Jiang described it as "magic blended with kung fu," noting that he was timid and apologetic during his first challenge but full of swagger by the second week.

"I'm amazed by how I've progressed," Jiang said. "When I get a 'no,' it's not a signal that I should run away looking for cover like I used to. Now, I see it as a time to negotiate a little bit." He's optimistic that his social experiment will have long-term effects, maintaining that it's "more scary" to solicit a burly stranger for a game of soccer than it is to broker an investment deal.

But can a brain really be acclimatized to rejection the way it can be trained for better memory, with staged, low-stakes experiments at Krispy Kreme? Can anyone learn to enjoy a thumb's down in the long run? While the emerging "antifragile" cohort seems to think so, psychologists aren't convinced.

"Rejection therapy might correct people who are overly sensitive so that they become more realistic" but it's unlikely to immunize anyone completely, said Kipling D. Williams, a professor of psychological sciences at Purdue University and co-editor of The Social Outcast: Ostracism, Social Exclusion, Rejection and Bullying. Williams said that while there are methods "therapists use to help patients realize that they catastrophize ideas about rejection," few people get to the point where they actually itch for the challenge of being turned down.

"I don't think there's a way to avoid the hurt of rejection fundamentally," said Guy Winch, a New York psychologist and author of Emotional First Aid: Practical Strategies for Treating Failure, Rejection, Guilt, and Other Everyday Psychological Injuries, which will be published next July.

Winch says rejection therapy is an offshoot of a behavioural technique called "flooding," which involves exposing yourself to fears in large doses. He points to the reality game show Fear Factor, as well as actors who audition constantly and telemarketers who cold-call all day – the hang-ups don't sting after a while. Still, that doesn't mean telemarketers are impervious when wifey runs off with the poolboy: "When we're doing a series of rejections, it makes it a little easier for us in the moment but that doesn't mean we become immune or resilient to rejection in the long run," said Winch, who recommends defining your expectations and hoping for the best but being prepared for the worst.

So why does rejection cripple some with insecurity but drive others to success? "We all have constitutional proclivities, how resilient we are, whether we tend to withstand certain things and persevere or give up easily or take things really personally. That has to do with our fundamental character," argued Winch.

Taleb's "antifragile" supermen aside, Winch and other experts aren't convinced anyone ever becomes so nonchalant that they lap up a "no." There are good evolutionary reasons for the stung response: Research has found being rebuffed activates the same neuro-architecture in the brain as physical pain.

"Rejection is so painful because ostracism from the tribe used to be a death sentence in our evolutionary past. Rejection was our early-warning system about being ostracized. That's why it piggybacked on the pain pathways," said Winch.

It makes sense to pick up on the cues that signal you might be on the outs with people, said Williams. "If you became totally immune to being rejected, you'd run the risk of alienating people because you're not correcting your behaviour."

In other words, sometimes it's wise to back away from the stranger's door with your soccer ball.

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