Ideas
101+ Rejection Therapy Ideas by Category and Difficulty
The master list gives you every idea in one place. This page organizes them by category and difficulty level so you can build a graduated practice that actually works. Start with beginner asks in the categories that matter most to you. Move to intermediate when those feel easy. Advanced when you are ready to push.
How to Use This Page
- Pick the category where you want to grow most
- Start at Beginner level. Do not skip ahead.
- Do one ask per day from that category for a week
- When Beginner feels easy, move to Intermediate
- Mix categories to build well-rounded asking confidence
Jump to a Category
Career & Work
The asks that move your career forward. Most people never make them because the stakes feel too high. They are not.
Beginner
01Ask a coworker for feedback on a specific piece of work
02Request to attend a meeting you are not normally invited to
03Ask your manager what one thing you could do differently
04Volunteer to present something at a team meeting
05Ask a colleague in another department to coffee
Intermediate
01Ask for a raise with specific data and a target number
02Pitch a project idea to your team or manager
03Ask what it would take to get promoted in the next 6 months
04Cold email someone you admire in your industry for advice
05Negotiate your benefits (remote days, PTO, equipment)
06Ask for budget to attend a conference or course
07Request to lead a cross-functional initiative
Advanced
01Apply for a job you think you are underqualified for
02Ask a competitor for coffee to learn from them
03Pitch yourself as a speaker at an industry event
04Ask for equity or profit-sharing at your company
05Request a department transfer to a role you want
06Send a follow-up after being ghosted on an application
07Ask an executive two levels above you for career advice
Dating & Romantic
The asks people rehearse in their head 50 times and never say out loud. Start at beginner. Work up.
Beginner
01Ask a friend to introduce you to someone they think you would like
02Ask a friend for honest feedback on your dating profile
03Start a conversation with someone new at a social event
04Compliment a stranger on something specific (not appearance)
05Ask someone at a class or event about themselves
Intermediate
01Send a thoughtful first message on a dating app (not just hey)
02Invite someone you just met to get coffee sometime
03Ask someone to dance at a bar or event
04Ask an acquaintance you find interesting to hang out one-on-one
05Respond to someone's story on social media and start a real conversation
06Ask someone at a gym or class if they want to grab food after
Advanced
01Ask someone for their number in person
02Ask someone on a date using the word date
03Tell someone you are interested in them romantically
04After a good first date, suggest a specific plan for date two before leaving
05Approach someone cold at a coffee shop or bookstore and introduce yourself
06Ask an ex for honest feedback on what you could do better in relationships
Creative & Business
Putting your work out there is an ask. Every submission, pitch, and share is a rep.
Beginner
01Share something you created publicly for the first time
02Ask a friend for honest feedback on something you made
03Post your work on social media without disclaimers or apologies
04Ask someone to collaborate on a small project
05Submit a comment or question at a talk, workshop, or webinar
Intermediate
01Submit your writing, art, or music to a publication or platform
02Send your portfolio to a dream client or company
03Pitch a guest post or guest appearance on someone else's platform
04Apply to a grant, fellowship, or residency
05Ask a brand for a sponsorship or partnership
06Enter a competition you think you will not win
07Pitch yourself to teach a workshop or class
Advanced
01Send your manuscript to a publisher or literary agent
02Ask a gallery, venue, or bookstore to feature your work
03Cold pitch a keynote or speaking slot at a major event
04Ask an investor for a meeting about your business idea
05Request a testimonial from your most prominent client
06Ask someone famous or well-known to review or endorse your work
Everyday Life
Low-stakes asks that build the muscle. These are where most people should start.
Beginner
01Ask a stranger for directions (even if you know the way)
02Ask a barista how their day is going and actually listen
03Request a free sample of something at a store or market
04Ask for a better table at a restaurant
05Ask someone in a store for their recommendation
Intermediate
01Ask for a discount at a store that does not advertise discounts
02Negotiate your cable, internet, or phone bill
03Request an upgrade at a hotel or airline counter
04Return something without a receipt
05Ask your landlord to fix something they have been ignoring
06Ask for a late fee waiver on a bill
07Ask a restaurant for a dish that is not on the menu
Advanced
01Ask someone in line if you can go ahead of them
02Negotiate the price on something that is not typically negotiable
03Ask a business to match a competitor's price
04Request a refund on something most people would not bother returning
05Ask your gym to waive the sign-up or cancellation fee
Online & Digital
The internet added a whole new category of rejection. Ghosting, unmatching, and silence are all digital nos.
Beginner
01Comment on a post by someone you admire with a real thought (not just an emoji)
02Reply to someone's story with a genuine question
03Post something personal or vulnerable on your social media
04Send a DM to someone you know but have never messaged
Intermediate
01Cold DM someone in your industry whose work you respect
02Ask someone on Twitter/X or LinkedIn to have a virtual coffee chat
03Pitch a guest post to a blog or newsletter you read
04Email a podcaster and pitch yourself as a guest
05Start a conversation in a Discord or Slack community you have been lurking in
Advanced
01Cold email a journalist about your story or project
02Reach out to an influencer about a collaboration
03Pitch your product or service to a large online publication
04Ask a well-known person in your field for a public endorsement
05Submit an op-ed to a major online publication
Track Every Ask
Ideas without tracking are just intentions. Log every ask, tag the category, and watch your rejection data build over time. See which categories you are going hard in and which ones you are avoiding.
Social & Friends
Building friendships as an adult requires the same ask-and-risk-rejection muscle as everything else.
Beginner
Intermediate
Advanced