self-mastery

Rejection Challenge

Last updated: 1/16/2026

[[rejection-proof]] Purpose of the rejection challenge: I want to improve my insecurities, which I think stem from my fear of rejection, being judged, people pleasing, etc. I think doing a challenge where the goal is to be rejected will improve that. I also want to embody the idea that social fears restrict our lives, and to not be attached to the outcomes of an interaction, but the process. In order to make my dreams come true, I need to face rejection. I am not the average person, and the average person is afraid of rejection. Approval seeking enhances the fear of rejection. It makes it sting more. It is outrageous that we are brought up as children to make others happy, and not us. We are taught to make God, our teachers, our parents, etc. happy, and we don't look inside ourselves.

A lot of fantastical stories, where someone does something impressive in an unconventional way, happen because the person doing it has less of a fear of rejection. Therefore, if you want this to happen to you, you will face rejection, but you will improve yourself.

Mantras for the rejection challenge: Life is random, meaningless, on your deathbed you won't remember or care about this. People's reaction towards you is only a reflection of them, not about you. Rejection is redirection. My attitudes are more important than my intelligence Count 3, 2, 1, and do it. Anxiety is fear of the future, which doesn't exist.

Rules for rejection challenge:

  • It needs to be over a long period of time, shoot for at least 66 days.
  • You must be outside your comfort zone.
  • You need to be vulnerable and put someone else in a position of power.
  • If you are asking for something, it needs to be something you actually want.
  • You don't need to "ramp" up the difficulty every time.
  • You must log your progress every day
  • You cannot go against your morals or values
  • You need to try your best, and be rejected, at least once a day
  • You need to be as authentic as possible. For example, if a rejection challenge is to ask a girl out, don't dress up all fancy that day, wear fragrance, etc. Do it as your authentic self.
  • You cannot explain you are doing a rejection challenge
  • You must ask "why" after a rejection
  • You need to stay engaged after hearing "no"
  • You must reflect on the rejection, the feeling, try to remove your agreements [[the-four-agreements|]]
  • Don't "significantly" go out of your way.
  • Ideally, the requests are in person, but it can be online.

Tips:

  • When asking for something, give a reason for the request
  • Acknowledge the other party's doubts
  • Smile, be positive, confident, open. You are a happy and charismatic person!
  • Have a lot of fun with it! Lead with warmth, engage conversation
  • Your thought pattern should be: "I have opportunity to do X" and then immediately do "X".

Ideas:

  • speak with the people at góralskie. they are afraid to talk with me and make conversation more than i am afraid to talk with them. they are waiting for permission to speak.

  • Compliment a stranger, especially if they are attractive, intimidating, and female. Do so regardless of your appearance.

  • Ask for a discount at a store

  • Invite a friend over when your room is messy

  • Do karaoke.

  • Join strangers playing a game (volleyball, basketball, etc.) even if you are not good at it

  • Ask someone to teach me how to do something, play an instrument, code, etc.

  • Do a public speech, lecture

  • Request to shadow a SWE for a day at a company I admire

  • Present side project at build illinois.

  • Request to beta test a product I wanna use.

  • Ask friends for date referrals

  • Request to do a different assignment, or submit the assignment differently

  • Post about my insecurities on social media

  • Post about my productivity setup on social media/my website

  • Email people I think are "above me" for advice, mentorship, etc. Example, smart glasses guy

  • Ask a stranger to sit by them, and then get to know them

  • Start a conversation with someone you admire on campus

  • Ask someone to collaborate together on a project

  • Extend a random invitation to hang out (wanna do homework together)

  • Go to the expresso royal for a cup of skim milk.

  • Go up to a group of people and ask if they wanna play tag

  • Knock on a random person's apartment and ask for an apartment tour

  • Speak over the costco intercom

  • Give a weather report at local news station

  • Email the cs225 professors and ask if you can give one of the lectures

  • Race a Random Person

  • Make My Own Sandwich at Subway

  • Sleep at Mattress Firm

  • Change Coffee Shop's WIFI Password

  • Interview the new chancelor.

  • Interview one of my heros

  • Be publically interviewed

  • Post nudes onlinegg

  • Do pole dancing

  • Message one of my heros and ask to collaborate. (Scott Young)

  • dance outside by myself, music in earbuds

  • publish a blog

  • publish a cringe X post

  • Publish this "asking for what I want" training on my website.

  • Ask a stranger to take a photo with me

  • Go to a fire station (at a non-emergency time) and ask if you can slide down the pole.

  • At a grocery store, ask an employee if you can see the "back room" or the stockroom.

  • Ask a restaurant if you can go into the kitchen and thank the chef personally.

  • Ask to sit in the driver's seat of a police car or delivery truck (when they are not busy, of course).

  • Line dance on the quad

  • Go to a teller and ask if you can see the inside of the vault "just for a minute."

  • Find a security guard and politely ask if you can "guard their spot" for two minutes while they take a quick break.

  • Go to a luxury car dealership (Mercedes, Tesla, etc.) and ask if you can take their most expensive car for a test drive, while being upfront that you have no intention of buying it today.

  • Ask a very attractive girl for a hookup

  • Ask a high quality woman for a date, call, etc.

  • Ask an employee if you can "test" the store's best camera by getting all the available employees together for a quick group photo.

  • Ask an employee if you can take a 10-minute "power nap" in one of the display beds to "properly test it."

  • Ask the bartender/barista if you can go behind the bar to pour your own drink or pull your own espresso shot (under their supervision, of course).

  • Find the person running the soundboard and ask if you can move one of the faders (volume sliders) up and down.

  • Sing for Dial a Carol

  • Find the "Eternal Flame" sculpture (near the English Building) and, as tradition holds, share a kiss with someone... or just take a great photo. Get a kiss

  • Go to a massive lecture you aren't enrolled in (like in Foellinger or Lincoln Hall). After it ends, go up to the professor and ask, "I really enjoyed your lecture. May I teach the first five minutes of your next class on Friday?"

  • teach a stranger a line dance at a party

  • line dance in public

  • sing in public

  • spark a conversation with a total stranger on the streets.

  • go on omegle

  • ask for free coffee from espresso royal

  • call strangers beautiful, handsome walking by (5x)

  • ask a girl sex? as the first message.

  • I saw a man at the library with a cool productivity setup. I wanted to talk with him but he was working. So I got a sticky note and wrote on it: "don't want to disturb, i appreciate your productivity setup, wanted to say hi, ... my number is [redacted], say hi!" and gave it to him. I smiled when I gave it to him, waved, and walked away. [[2025-11-28]]

  • talk to a man at a concert i didn't know

  • ask girl out on a date