November: A Month of Rejection Challenges

November: A Month of Rejection Challenges

One of my New Year’s resolutions this year was to conquer my fear of rejection by getting rejected at least 100 times trying 100 different things. I have done quite a few things to that end: I’ve taken several Improv classes, and I’ve tried a couple of self-directed rejection challenges here and there. Admittedly, I haven’t kept great track of where I am out of 100 different ways to get rejected, and I still have a moderate fear of rejection which is currently manifesting itself as a resistance to putting my work as a self-employed individual into the world for real feedback.

In an effort to fight back and make real progress toward this goal before the year ends, I’m trying something a little different with November: I’ve asked six friends to each give me five rejection challenges of varying difficulties for 30 challenges total, enough to do one a day for each day in November.

Why am I doing this?

The short version is that I read Rejection Proof (affiliate link), a book about Jia Jiang’s mission to get rejected once a day for 100 days and everything he learned from the experience. Reading his book made me realize that I am acutely afraid of rejection, judgment, and just plain looking silly; that that fear limits me; and that I also could potentially learn a lot from being rejected a whole bunch of times. The longer version of the story is that this is part of a larger campaign to challenge my fears and cultivate courage–topics about which I’ve written a (at time of writing unfinished) series of posts.

Of course, the goal isn’t to reach a point where I completely disregard others’ opinions–that’s called being a sociopath, and I certainly don’t want to get there. The hope is, however, that a lessened fear of rejection, and a weaker preoccupation with what others think of me will lead to a greater sense of self-acceptance, a higher degree of authenticity in all of my interactions, and the courage to ask people for what I really want.

What is a rejection challenge?

Loosely described, a rejection challenge forces me into a scenario where I need to ask someone for something to which the answer could be “no” (or, equivalently, to which the answer could be something I don’t like or maybe don’t want to hear, e.g. negative feedback). The challenges I have here are all over the place ranging from simple and easy requests, to requests that are just completely ridiculous and awkward, to requests that require me to bother people I wouldn’t otherwise bother, to requests for things that I might actually feel somewhat emotionally invested in. These challenges are designed to make me cringe, and I imagine that they will be extraordinarily cringeworthy (and/or just amusing) to watch.


By asking friends for challenges rather than coming up with them myself, I’ve added some very acute social pressure to actually follow-through, and by publishing this post, I’m adding some additional public accountability to the mix. I’ll be making every effort to do one of these challenges every day, and if I can figure out how to make it work, I may even vlog them on YouTube so everyone I know can make fun of me (in a sense, this is its own rejection challenge). At the very least, you can expect that I’ll write about the more interesting or informative experiences.

The Challenges

Without further ado, here are the challenges rank ordered by approximate relative difficulty scored out of 10:

  1. 2: Smile, make eye contact with, and ask for a high-five from every person you encounter while walking down 2 blocks of street (or equivalent distance in a mall).
  2. 3: Ask a waiter to take you to the kitchen and meet the chef/see how things get made.
  3. 3: Ask a homeless person if they will eat dinner with you.
  4. 3: Ask a homeless person to tell you their life story.
  5. 4: Ask to make your own sandwich at Subway.
  6. 4: Go to a mattress store and ask to take a nap in one of their beds.
  7. 4: Go to a convenience or grocery store and ask to speak over their intercom system.
  8. 4: Go to a burrito joint and ask if you can come behind the counter and call out a few orders.
  9. 4: Ask to help prepare something in a food truck.
  10. 4: Call the office of the Mayor of San Diego and ask for a meeting.
  11. 5: Challenge a stranger on the street to an impromptu chess game.
  12. 5: Ask 3 strangers if they will play a quick game of Simon Says with you.
  13. 5: Ask to walk a stranger’s dog.
  14. 5: Ask a running stranger if you can jog with them.
  15. 5: Ask 2 people to jump into the Pacific Ocean with you.
  16. 5: Offer to autograph a stranger’s hand with a sharpie.
  17. 5: Try to sell a roll of paper towels to a mall stall vendor or street-side vendor.
  18. 6: Ask 3 strangers if they can text you a screenshot of their phone’s home screen.
  19. 6: Ask someone if you can create chalk art in their driveway.
  20. 6: Ask 10 people on public transit (or at the beach!) what they’re listening to and try to turn it into a conversation.
  21. 6: In a crowded place, ask a stranger if they’d be willing to pose with a potato mango as if they were in the Lion King while you take a picture.
  22. 6: Ask a stranger to join you as you walk like a crab for at least 1 block on a fairly busy sidewalk (or until you pass at least 3 people, whichever happens last).
  23. 6: Ask a stranger to swap shoes with you for a block.
  24. 7: Carry a rubber chicken around, and ask a random stranger if they will kiss it.
  25. 7: Ask someone to give up their seat for you on public transportation. (Bonus: Do this when there are empty seats around them.)
  26. 7: Ask a stranger to apply sunscreen to your face.
  27. 7: Try to convince a stranger to feed you a banana.
  28. 8: Spend at least 30 minutes busking in a crowded place. Explicitly walk up to someone at the end of a performance and ask for some money.
  29. 8: Go to a karaoke bar, a stand-up venue, or something similar. Perform, and then explicitly ask a stranger from the crowd for feedback afterwards.
  30. 9: Apply to be a chef on Feastly. If approved, host a pop-up kitchen event and cook for a bunch of strangers through Feastly. Ask them for their honest opinions after the meal.

Closing Thoughts

Are some of these challenges incredibly socially awkward? Yes. Do some of them force me to break social norms? Absolutely. Will they get me in trouble? I’m really hoping not. Are all of these completely realistic rejection scenarios? Of course not. Do I think they’ll teach me something anyway? Definitely.

Regardless of whether they are realistic or contrived, socially acceptable or socially awkward, all of these challenges will put me in situations that make me at least a little bit uncomfortable. As I’ll elaborate in a soon-to-be-published post, learning to act in spite of that discomfort and that fear is an important part of what I’ve learned to call courage.

Wish me luck!


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Interested in keeping up with the challenges? Please consider subscribing to be the first to know as new content comes out!

Have a great rejection challenge idea? Tell me about it in the comments below, and I may end up doing it later this year!

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