The Rejection Game: How Being Willing To Lose Can Help You Win Big

In May 2013, I was at the lowest point of my life. After two years of hustling and sleeping in the trunks of our cars to save money, my friends and I were a month into what we thought would be a four-month adventure across America.

On the way to Austin, our RV died. With no money to fix her, it seemed like the adventure, and the preceding two years of miserably hard work, were both slipping away.

That’s when we met TEDx motivational speaker and self-described “Rejection Therapist,” Jia Jiang. He made us play The Rejection Game, and everything turned around.

The rules are simple:

1. Ask strangers for something ridiculous

2. Try to convince them

3. See what happens

Here’s how it went down.

Now, of course, is when I challenge everyone to play the rejection game. Fair warning: It will be a lot of fun, but it will seem like you’re wasting your time… at first.

The more you play the game, however, the more you get out of it. I’m sure you’re a cynic; when I heard about the game, no one was a bigger cynic than me. Still, it sounded like it could at least be entertaining, and I was in a defeated mood, so I gave it a shot.

For the first few challenges, I couldn’t help shake the fact that I didn’t need this. The point, as I understood it initially, was to desensitize myself to rejection and learn that it’s not the end of the world. The idea behind it is that with our currently defective job market, countless Millennials are sitting on their dreams and oftentimes, college degrees, as well.

There are few clear paths to a secure future, and the idea of charting your own course is so terrifying that most of us don’t even consider it. But why is it terrifying? According to my new therapist, Jia Jiang, it’s a basic fear of rejection.

Maybe it’s the participation trophies or our front row seats to the lethal injection of industrialism, but if we can just learn to cut through the stigma of rejection and realistically weigh the outcomes, maybe we wouldn't be so afraid.

So, I begrudgingly agreed to play the game. At first, it was rejection after rejection. This was fun, of course, but I didn’t really feel like I was getting anywhere.

Then, my luck started to change. After each initial rejection, I starting doing what Jia referred to as “negotiating the no.” Basically, humans all want to get along. The more I showed respect and care, the more strangers seemed to be willing to give me. Accidentally, I was taking a better negotiation class than any college could offer.

By the end of the weekend, I was completely unflappable. The lesson I was sure I didn’t need turned out to be one of the best I have ever had in my life.

Yes, I was desensitized to rejection, but it didn’t end there. I learned how valuable it can be to ask for something, how much kindness is inside pretty much everyone in this amazing country and how easy it can be to find success.

Even if the way you search for it is new and different, it does not have to be terrifying.

So, challenge yourself. Play the rejection game and see how being a loser on purpose can teach you to win at life. For more on Jia Jiang and his story and program, check out this interview. Also check out Jia’s very own 100 Days of Rejection at