341 — How to Overcome Your Fear of Rejection: What 100 Days of Rejection Therapy Taught Jia Jiang

August 13, 2026

Have you ever been afraid to ask for something because you were afraid you’d get rejected? Whether you want to invite someone on a date or ask for a raise, the fear of hearing “no” can keep you from trying.

But according to my guest today, the sting of rejection probably isn’t as painful as you think. But the cost of avoiding rejection might be worse.

My guest is Jia Jiang, the founder of 100 Days of Rejection, where he set out to get rejected on purpose every single day for 100 days straight. He’s the author of Rejection Proof, and his new book Easy Discipline is coming out soon.

Some of the things we discuss are:

What Jia learned from asking a stranger for $100, requesting a burger refill, and knocking on random doors to ask if he could play soccer in the yard
The Krispy Kreme Olympic donuts story that went viral (and briefly moved the company’s stock)
The mental script that runs in your head before you ask for something — and why it’s almost always wrong
The single shift that turns you from someone who mirrors other people’s energy into someone whose energy sets the tone
Why “no” isn’t the end of a conversation — it’s the start
The one line that lowers the temperature on any high-stakes ask (and gets you more yeses)
The story of Mike, whose fear of rejection nearly cost him the ability to advocate for his wife when she was diagnosed with cancer
Why “you either get a yes or an epic story” might be the most freeing thing you’ll hear all week
The Therapist’s Take: My top three strategies for becoming more rejection-proof starting today

Key Takeaways:

Rejection Isn’t Failure: It can be an opportunity to start a productive negotiation.
Mindset and Energy: If you’re convinced you’re going to be rejected, you’ll reduce your chances of success.
Learning from Denial: Rejection therapy can help you leverage humor and creativity to reduce the fear of being rejected.
Resilience Building: Regularly facing rejection in low-stakes scenarios increases resilience and confidence.

Notable Quotes:

"On '100 Days of Rejection,' I set out to get rejected on purpose every single day for 100 days straight."

"The thing about rejection is, I learned that people's initial no’s often mean, 'Tell me more.'"

"When I'm relaxed, people react differently. Your energy can reshape an entire interaction."

"You either get a yes or you get an epic story."

"There are life-or-death implications to overcoming your fear of rejection, especially when advocating for your health or your loved ones."

Timestamp Summary

0:00 — The mental script that plays before you ask for something—and why it's almost always wrong

2:29 — The single rejection that made Gia want to quit his own dream

5:02 — Why he skipped the TED talks and books and went a completely different route

6:30 — The Krispy Kreme request that should have been a no (and went viral)

11:39 — What Gia saw watching the rejections back that changed everything

17:32 — The subconscious mirroring happening in every conversation you have

21:19 — The exact script for asking your boss for a raise without triggering pushback

25:32 — Why "no" isn't the end of the conversation—it's the start

31:00 — The letter from Mike that turned this from a fun experiment into something bigger

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