100 Days of Rejection Challenge: overcome your fear of rejection

Most people hate getting rejected, so this 100-day rejection challenge is tough. (I still need to do it…)

Jia Jiang had an embarrassing experience when he was six years old. He was publicly 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, me, 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 learned a lot.

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 tried creating a positive learning experience by giving a gift-giving lesson.

  • 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 it to someone else, who would then come up, choose another gift, and give it to someone else.
  • This beautiful process of giving and receiving would repeat until every student had a gift and a compliment, fostering a sense of unity and community.

In the end, Jia 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 people can come up with something nice to say next year.

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

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

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

We need to try different things and pay attention to results to optimize our actions.

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 started his own company. He was rejected for 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.

One strategy he used was to search the Internet for “How do I overcome the fear of rejection?”

  • He found many 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 that these websites didn’t talk about how to overcome rejection. Jia 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, a game that essentially encouraged people to go out for 30 days and get rejected every day at something.

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

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

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

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 that 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 on his video blog. At home, when he was reviewing the footage (kind of like how 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 look scary. 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.

Jia 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 to run away.

Jia recognized that whenever he felt 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 disappointed when we don’t get an excellent mark.
  • We develop this fixed mindset that we must be fantastic at everything the first time we try something.
  • So, we run away from trying harder or being curious about our mistakes.

Many teachers are comfortable presenting in front of their students, but they find talking and sharing ideas at a staff meeting challenging.

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

After reviewing the video footage, Jia decided that the next strategy he would try was to stay engaged rather than run away.

Overcoming Rejection – Strategy #3 : Stay engaged and keep talking when they say no.

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

He talked with the cashier, who said that they didn’t do burger refills. What I find surprising is that he had a longer conversation than last time before he got rejected. I would’ve run away when the cashier said no.

But Jia used the strategy of staying engaged and talking after they said no (instead of running away). He continued to explain how much he loved the burgers and 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 we learn from Jia? What works?

After his burger refill request was rejected, Jia reflected on what had 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 Jia tells is about going to Krispy Kreme and asking for five donuts interlinked to look like Olympic rings.

The manager took him seriously, and 15 minutes later, he 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 was to become less afraid of rejection. However, an interesting side effect was that he got 5 million views on YouTube.

This event brought him some notoriety, but Jia talks about how his real goal was to learn.

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

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

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

Jia gave an example of knocking on a stranger’s door and asking if he could plant a flower in the backyard. The person immediately said no, but before he could leave, Jia asked, “Hey, can I know why?”

The person explained that he had a dog that would dig up everything in the backyard, but if Jia wanted to do this, he should go across the street and ask his neighbor, Connie. So that’s what Jia did.

Reflecting on what had happened, Jia 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, or because he didn’t look good.

He realized “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 said, “I also learned that I can actually say certain things and maximize my chance to get a yes.” This is about optimizing your actions 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 Jia asked, “is that weird?” And the manager say, yes, a little bit weird. Jia talks about how the manager’s demeanor changed as soon as he said that.

So, he was allowed to be a Starbucks greeter for the next hour. Jia reflected that he could do this because he mentioned, “Is that weird? “I mentioned his doubt. And because I mentioned, “Is that weird?” That means I wasn’t weird.

Jang noticed that he repeatedly had this experience where if he mentioned some doubt that people might have before he asked the question, he gained their trust.

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

Here’s the video with the Starbucks Greeter:

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

Jia talks about how he realized 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. He was rejected.

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

Jia 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: Jia thought he would have to accomplish great things to be an entrepreneur or teacher, 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. It can become your gift.

Jia researched rejection. People who change the world are often met with initial and frequently 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 that they let their own reaction after rejection define themselves. They embrace the rejection.

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

But he started embracing it, turning it into the most significant 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 Jia’s “why” in life. He writes about this on his blog, book, TED talk, and app.

The final message in the TED talk is that 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 ten 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 those differences produce different results?

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

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