🎯 30 Rejection Therapy Challenges Ranked by Difficulty
A complete list of 30 rejection therapy challenges from easy to extreme. Start with day 1 and work your way up as your confidence grows.
In this article
Easy Challenges (Days 1-7)
1. Ask a stranger for the time (even though you have a phone) 2. Ask for extra napkins at a restaurant 3. Ask a store employee for their honest opinion on a product 4. Ask someone in line if you can go ahead of them 5. Ask for a glass of water at a business that doesn't serve food 6. Ask a stranger to take your photo 7. Compliment a stranger and ask them about their day
Medium Challenges (Days 8-15)
8. Ask for a 10% discount at a store that doesn't offer one 9. Ask to pet someone's dog and have a full conversation about it 10. Ask to sit at a stranger's table at a busy restaurant 11. Ask someone to watch your bag while you use the restroom 12. Ask your barber/stylist for honest feedback on a side project 13. Ask a restaurant if you can see the kitchen 14. Request a free sample at a place that doesn't offer them 15. Ask someone to teach you one thing they know
Hard Challenges (Days 16-23)
16. Ask for a free upgrade at a hotel or rental car 17. Negotiate your monthly bill (phone, internet, gym) 18. Ask a stranger if you can give a 30-second speech about anything 19. Ask someone you admire to be your mentor for 30 minutes 20. Return something to a store without a receipt 21. Ask your boss for honest feedback on your biggest weakness 22. Ask to borrow something valuable from a neighbor 23. Ask a business owner what their biggest challenge is
Extreme Challenges (Days 24-30)
24. Ask a stranger if you can make an announcement in their business 25. Cold-pitch your product/idea to someone in person 26. Ask to speak at a local event or meetup 27. Ask a CEO of a company for 15 minutes of their time 28. Negotiate your rent or salary 29. Ask someone to introduce you to the most important person they know 30. Ask 10 people in one day for something — a "rejection marathon"
Tips for Success
Start every challenge before noon. The longer you wait, the more your mind builds the fear. Log every attempt immediately — even the chickened-out ones. Those are data too.
And remember: the goal is NOT to get a yes. The goal is to get comfortable hearing no. A rejection is a successful attempt.
Free Tool: Rejection Therapy Tracker
Track your progress through all 30 challenges with our free tracker — logs your fear level and shows your courage growing over time.
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