That night, I sat at my kitchen table with a notebook, a laptop, and an unhealthy amount of coffee. If I was going to deliberately seek out 1000 rejections, I needed a system. I needed rules. Most importantly, I needed to understand what I was really trying to accomplish.
The internet rabbit hole began innocently enough. I searched for "overcoming fear of rejection" and discovered I wasn't alone in this struggle. Far from it. Study after study showed that fear of rejection was one of humanity's most universal anxieties, rooted in our evolutionary need to belong to the tribe. In prehistoric times, rejection from the group meant death. Our brains, it turned out, hadn't gotten the memo that social rejection in the 21st century wasn't life-threatening.
I found stories of rejection therapy, a concept where people deliberately seek out rejection to desensitize themselves to the fear. There was the man who asked for Olympic symbol-shaped donuts at Krispy Kreme. The woman who requested to make announcements over grocery store intercoms. The entrepreneur who asked strangers if he could sit in their cars.
But most of these were one-off experiments or short-term challenges. Nobody, as far as I could find, had committed to a full year. Nobody had aimed for 1000 rejections. The sheer scale of what I was proposing started to sink in.
I needed rules. Clear, specific guidelines that would keep me honest and push me outside my comfort zone without turning me into a nuisance. After several drafts and one wine-fueled revision session, I landed on these:
The 10 Commandments of Rejection
1. Every rejection request must be genuine. No asking for things I don't actually want just to get a "no." If someone says yes, I have to follow through.
2. Categorize everything. Professional, Personal, Creative, Social, Financial, and Wild Card. Aim for balance across categories.
3. No repeat requests to the same person unless significant time has passed or circumstances have changed.
4. Document everything. Date, request, response, emotional impact, and lessons learned. No selective memory allowed.
5. Push the edge, but stay ethical. No requests that could harm others, violate laws, or damage relationships unnecessarily.
6. Rejection by non-response counts after a reasonable waiting period (one week for emails, immediate for in-person).
7. Track emotional impact honestly on a scale of 1-10. No tough-guy pretending it doesn't hurt.
8. Share the journey. Weekly accountability check-ins with someone who won't let me quit.
9. Quality over quantity when both are possible. Better to ask for one meaningful thing than ten trivial ones.
10. When someone says yes, celebrate it, but it doesn't count toward the 1000. This is about collecting no's, not yes's.
With rules in place, I needed a tracking system. The spreadsheet would be my primary tool, but I also bought a physical journal. There was something about writing rejections by hand that felt like it would make them more real, more processed.
I divided my categories and brainstormed potential rejection opportunities for each:
Professional: - Salary increases - Promotions - High-profile project assignments - Speaking engagements - Media interviews - Board positions - Consulting opportunities - Partnership proposals
Personal: - Dating and romantic pursuits - Friendship invitations - Family boundary requests - Personal favor asks - Lifestyle upgrade requests - Service improvements - Discount negotiations
Creative: - Publishing opportunities - Art show submissions - Performance invitations - Collaboration requests - Grant applications - Competition entries - Workshop teaching
Social: - Party invitations - Group membership - Leadership positions - Event speaking - Social media connections - Networking meetings - Community involvement
Financial: - Investment opportunities - Loan applications - Price negotiations - Refund requests - Upgrade appeals - Sponsorship asks - Fundraising attempts
Wild Card: - Random acts of boldness - Impossible requests - Stranger interactions - Comfort zone explosions - Adventure invitations - Unusual experiences - "Why not?" moments
Looking at these lists, I felt simultaneously excited and terrified. The sheer variety of ways I could get rejected was overwhelming. But that was the point. If rejection was everywhere, then so was opportunity.
The final piece of my system was accountability. I needed someone who would call me out if I started slacking, someone who wouldn't let me quit when things got hard. The obvious choice was my best friend, Mike, who had been watching my play-it-safe approach to life with increasing frustration for years.
I called him that night and explained the experiment. There was a long pause after I finished.
"You're going to ask for 1000 rejections," he said slowly. "On purpose."
"That's the plan."
Another pause. Then: "This is either the dumbest or most brilliant thing you've ever come up with. I'm in. Weekly check-ins, full transparency, and if you try to quit, I'm going to remind you of every opportunity you've let slip by until you get back on track."
"Deal."
"So when do you start?"
I looked at my phone. Morrison Industries still hadn't responded to my email from that morning.
"I already have."
That night, I lay in bed staring at the ceiling, wondering what I'd gotten myself into. 1000 rejections. The number felt impossibly large. But then I remembered the spreadsheet from that morning – 47 opportunities avoided in just one year. At that rate, I'd been pre-rejecting myself over 100 times annually for my entire adult life.
Maybe 1000 wasn't too many after all. Maybe it was just the beginning of making up for lost time.
I opened my journal and wrote my first entry:
Day 1. Rejection Count: 1 (pending). Today I finally sent an email that had been sitting in my drafts for three weeks. Win or lose, at least it's out there. Tomorrow I'll aim for three rejections. The journey of 1000 no's begins with a single ask.
Little did I know that by tomorrow evening, I'd have a response from Morrison Industries that would set the tone for the entire experiment – just not in the way I expected.