100 Days of Rejection Challenge: overcome your fear of rejection

Most people hate getting rejected so this 100 days rejection challenge is tough. (I haven’t done it, yet…)

Jia Jiang had an embarrassing experience happen to him when he was six years old. He was publically rejected, and it held him back from achieving his goals… until he figured out a way to overcome his fear of rejection.

Jia is like you and I and everyone else around us. Nobody likes being rejected. No one likes asking for something, and being told, no! But Jia figured out a way to work smarter and he learned a lot along the way.

We can look at his story and figure out some strategies, optimization, and tinkering that he did to overcome the obstacle of fear of rejection:

Obstacle: Fear of Rejection

In grade 1, his teacher was trying to create a positive learning experience by combining gift giving with .

  • There were 40 students in the class.
  • The teacher bought enough gifts for everyone to get one.
  • Students would come up one-by-one, choose a gift and give a to someone else, who would then come up choose another gift and give a to someone else.
  • The process would repeat until everyone received a gift and a compliment.

At the very end, Jia Jiang was one of the last three students. He was crying because no one had anything nice to say about him. The teacher told them to get a gift and sit down. Oh, and be nicer so that next year people would be able to come up with something nice to say.

This initial rejection and fear of rejection would stay with Jia as he grew up.

Even though Jia Jiang wanted to become an entrepreneur and conquer the world, he didn’t because he was afraid of rejection.

Sometimes, effort alone isn’t enough to reach our goals.

We need to try different and to pay attention to results to optimize what we are doing.

At age 30, he was a marketing manager for a company, but he wasn’t going anywhere. Jia felt stuck and stagnant. And he says, it’s not because he wasn’t putting in the effort, it was because he was afraid of rejection. That was the obstacle.

Jia talks about a time when he was 30 and he started his own company and he was rejected by an investment opportunity. He wanted to quit, but he thought of his idol Bill Gates: Would Bill Gates quit?

So, Jia decided that he wanted to become a better leader. A better person.

A strategy he used was to search on the Internet, “how do I overcome the fear of rejection?”

  • He found a bunch of psychology articles talking about where fear of rejection comes from.
  • He found a bunch of inspirational articles with obvious clichés like, “don’t take it personally, just overcome it.”

The problem was theses websites didn’t talk about how to overcome rejection. He needed a strategy.

100 days of rejection challenge – Strategy #1: Go out there and get rejected 100 times to desensitize yourself from the pain of rejection

Finally, he found rejectiontherapy.com which was a game and essentially encouraged people to go out for 30 days and get rejected every day at something.

The goal was at the end of 30 days of rejection, you desensitize yourself from the pain of rejection.

Jia Jiang took the strategy and decided instead of 30 days of rejection, he would try to get rejected 100 days.

To keep himself accountable and honest, he decided to make a video blog of his efforts. He brainstormed a bunch of things he could do to get rejected and videotaped himself doing it.

Overcoming Rejection – Strategy #2: Run away when they say no

Jia decided to borrow $100 from a stranger. So he went to work, and asked a really big guy. The guy said no, and Jia felt so embarrassed, he ran away.

Here’s the first video about borrowing $100 from a stranger.

Tinkering is when we discover something by accident and we wonder…

Jia had filmed his conversation to post it on his video blog. At home, when he was reviewing the footage (kind of like the way sports teams review gameplay), he noticed how scared he was…

But he also noticed that the other person who said no – well, he didn’t really look scary. In fact, the other person even asked Jia to explain himself, but Jia used a strategy of apologizing and running away. (Which didn’t work. He didn’t get $100 from a stranger.)

This is where Jih tinkered a little bit and played around with the idea. He watched the footage of his rejection and came up with other strategies:

  • he could’ve explained,
  • he could’ve negotiated.
  • But he didn’t do any of that. The strategy he used was run away.

He recognized that every time he felt even just the slightest bit of rejection, he would run away from the situation as fast as he could. A lot of us are like that.

As a student, it’s hard to get feedback from the teacher.

  • We’re really disappointed when we don’t get a great mark.
  • We develop this fixed mindset that we have to be fantastic at everything the first time we try something.
  • So, we run away from trying harder, or from being curious about our mistakes.

As teachers, a lot of us are fine to present in front of our students, but we find talking and sharing ideas at a staff meeting really hard.

  • Or asking for something from the principal can be really difficult.
  • Or saying no to a colleague asking for help is guilt-ridden.
  • Or we shy away from finding the courage to speak up about an issue that is important to us.

So, after the video footage Jia had decided that the next strategy he would try would be to not run away and stay engaged.


Overcoming Rejection – Strategy #3 : When they say no, stay engaged and keep talking.

This time, Jia went up to a restaurant, and asked the person for a burger refill – kind of like a drink refill, but with burgers.

He had a conversation with the cashier, but the cashier said that didn’t do burger refills. What I find surprising is that he had a longer conversation than last time before he got rejected, so personally I would’ve felt I had stayed engaged and could run away when the cashier said no.

But, Jia used the strategy of staying engaged and talking after they say no (instead of running away.) And so he continued to explain how much he loved the burgers and loved the restaurant, and if they did a burger refill, he would love them even more.

The cashier said something about asking the manager about it, but they couldn’t do it today. Sorry.

So after the second rejection, Jia left. Here’s the video:

Overcoming Rejection – Optimization Tip: Pay attention to your results

What can you learn from them? What works?

After the burger-refill rejection, Jia reflected on what happened.

  • He noticed that the life-and-death feeling wasn’t there
  • He had a growth mindset: Even though he was rejected, he had a positive learning attitude: “wow, great, I’m already learning things.”

Overcoming Rejection Tinkering idea: Play around with rejection and see what you can learn

The third rejection story that Jia gives us is about going to a Krispy Kreme and asking for five donuts interlinked that look like the Olympic rings.

The manager actually took him seriously and 15 minutes later, came out with the box of doughnuts.

That video got over 5 million views on YouTube.

Which is interesting from a tinkering perspective because his goal is to become less afraid of rejection. But an interesting side story was that he got 5 million views on YouTube.

This event brought him a little bit of notoriety, but Jia Jiang talks about how his real goal was to learn.

He turned this 100 days of rejection into this playground, this research project. In short, he was tinkering. He was just exploring: “I wanted to see what I can learn.”

Overcoming rejection – Strategy #4: When they say no, ask why: “hey, can I know why?”

One thing he learned, was if he doesn’t run, if he got rejected he could actually turn a “no” into a “yes,” and the strategy he used, was to ask why.

Jia Jiang gives an example of knocking on a stranger store and asked me if you could plant a flower in the backyard and the person said immediately no, but before he could leave, Jia Jiang asked, “hey can I know why?”

The person explain, that he had a dog that would dig up everything in the backyard, but if Jia Jiang really wanted to do this thing he should go across the street and asked his neighbour Connie. So that’s what Jia Jiang did.

Reflecting on what had happened, Jia Jiang talks about how if he had left after the initial rejection, he would think that the guy didn’t trust him, because he was crazy because he didn’t dress up well, because he didn’t look good….

He realized it was, “it was because what I offer did not fit what he wanted.”

Here’s the video about planting a flower in someone’s yard.

Overcoming rejection – Strategy #5: Before you ask for something, mention the doubt that they are having (to acknowledge their viewpoint and to gain trust)

Jia Jiang learned that “I also learned that I can actually say certain things and maximize my chance to get a yes.” This is about optimizing what you do to get a better return.

He went to a Starbucks, and asked the manager if he could become a Starbucks greeter. The manager wasn’t sure about this, but Jiang asked, “is that weird?” And the manager say, yes a little bit weird. Jang talks about how as soon as he said that his whole demeanour change.

So, he was allowed to be a Starbucks reader for the next hour. And Jiang reflected that he could do this because he mentioned, “is that weird?” – “I mentioned the doubt that he was having. And because I mentioned, “is that weird?”, That means I wasn’t weird.”

In this meant that Jiang was actually thinking just like him that he wasn’t actually weird – seeing this is a weird thing.

Jang noticed that over and over again he would have this experience that if you mention some doubt that people might have, before he asked the question, he gained their trust.

As a result, he optimizes his chance that people would say yes to them.

Here’s the video with the Starbucks Greeter:

Overcoming Rejection – Tinkering aha moment #1: Just Ask. (It might be easier than you think)

Jia talks about how he realized that he could fulfill his life dream (of teaching) just by asking.

He wanted to teach a college class so he knocked on a few professors’ doors and asked if he could teach their class. And he got rejected.

The strategy he used just keep asking. On the third try, the professor was very impressed.  

Jia Jiang used a strategy of being prepared: he came in with his lesson ready and a PowerPoint prepared. The professor said yes, come back in two months and I’ll fit you into my curriculum.

This was a pivotal moment: Jang thought that he would have to accomplish all these things you have to be, great entrepreneur or get a to teach, but no, he just had to ask for what he wanted…

Here’s the video about teaching a college class.

Overcoming Rejection – Tinkering aha moment #2: Embrace your obstacle instead of running away from it, and it can become your gift.

Jiang did research about rejection. The people who change the way we live, and the way we think are the people who were met with initial and often violent rejections.

He gives examples of Martin Luther King Jr., Mahatma Gandhi, and even Jesus Christ – these people did not let rejection define them.

A pivotal idea is they let their own reaction after rejection define themselves. They embrace the rejection.

Jia Jiang talks about how rejection was the biggest demon in his life. It was the worst thing in his life.

But, he started embracing it, and he turned it into the biggest gift in his life.

He didn’t ask to have that negative experience, but he owned it and took responsibility for growing from it.

“I started teaching people how to turn rejections into opportunities.”

This negative moment has become “why” in life. Jia writes about this on his blog, his book, his Ted talk, and his app.

The final message in the TED talk is when you face your next obstacle, don’t run. Embrace it, and they might become your gifts as well.

Discussion Questions: Would these strategies to overcome rejection work for you?

  • Which strategy is the best one for you to try?
  • Which strategy is the hardest one for you to try?
  • What strategy might also work?

Personal Challenge:

  • Option 1: Try a rejection challenge.
  • Option 2: Do one thing every day that scares you (because you’re afraid of failing, or being rejected.) Try this for 10 days in a row.
  • Option 3: Try this fail challenge:

After you try the personal challenge, see if you agree with Jia’s findings.

  • What’s the difference between what you did, and what Jia did. How might does differences produce different results?

Would you be up for the 100 days of rejection challenge?

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