The Morrison Industries CEO never responded. After a week of refreshing my email every ten minutes, I marked it down: Rejection #1, Professional Category, Non-response, Emotional Impact: 6/10.
Six felt honest. It stung more than I expected, probably because I'd built it up so much in my mind. But I had 999 more to go, and I was already behind schedule.
Day 8 of the experiment found me at my regular coffee shop, the one where I'd been going every morning for two years. The one where the beautiful woman with the auburn hair and the stack of architecture books had been sitting at the same corner table for at least six months. The one where I'd perfected the art of sneaking glances while pretending to read emails on my phone.
Today would be different. Today, she would be Rejection #2.
I'd practiced my approach in the mirror that morning. Casual but confident. Friendly but not creepy. "Hi, I'm David. I've noticed we're both regulars here, and I'd love to buy you a coffee sometime and hear about those architecture projects you're always working on."
Simple. Direct. Rejection-worthy.
I ordered my usual – large dark roast, no room – and turned to survey the shop. There she was, same corner table, surrounded by her usual fortress of books and blueprints. My heart rate doubled.
This is what I'd been avoiding for six months? Walking twenty feet and saying thirty words?
I took a breath, gripped my coffee cup like a lifeline, and started walking. Fifteen feet. Ten feet. Five feet.
That's when everything went wrong.
My phone buzzed. Without thinking – muscle memory from years of immediate response habits – I glanced down at the screen while still walking. Morrison Industries. The CEO had finally responded.
I never saw the laptop cord stretched across the aisle.
My foot caught. Coffee cup went flying. Hot liquid everywhere. I tried to catch myself but only succeeded in taking down the neighboring table's umbrella stand. The crash was spectacular.
When I finally stopped moving, I was on my hands and knees in a puddle of coffee, surrounded by scattered umbrellas, with every eye in the coffee shop on me. Including hers.
"Oh my God, are you okay?" The auburn-haired architect was suddenly beside me, her hand on my shoulder. Up close, she was even more beautiful than I'd realized. Also, I had coffee on my face.
"I'm... yes. Fine. I'm fine." I struggled to my feet, dripping. "I'm so sorry about—"
"Here, let me help." She grabbed napkins from her table and started dabbing at my shirt. "That was quite the entrance. I'm Jennifer, by the way."
"David," I managed. "I, uh, I was actually coming over to—"
"To ask me out?" She smiled. "I know. You've been working up to it for months. I was starting to think you never would."
I stared at her, coffee dripping from my chin. "You knew?"
"You're not exactly subtle with the looking. It's flattering, honestly. But maybe next time lead with words instead of interpretive dance?"
Despite the embarrassment, I laughed. "This wasn't exactly how I planned it."
"Plans are overrated." She handed me more napkins. "Look, I need to get to a client meeting, but here's my card. Call me when you've dried off, and we'll get that coffee. Well, I'll get coffee. You've had enough for today."
She gathered her things while I stood there like an idiot, holding her business card and dripping on the floor. At the door, she turned back.
"Hey David? For what it's worth, if you'd asked six months ago, I would have said yes then too."
The door chimed as she left. I looked around the coffee shop at the amused faces, the patient barista waiting with a mop, the disaster zone I'd created.
Then I looked at the card in my hand. Jennifer Chen, Senior Architect.
This wasn't a rejection. This was Acceptance #1.
I helped clean up the mess, left a massive tip, and stumbled back to my car in a daze. In the parking lot, I finally checked the Morrison Industries email:
David, I apologize for the delayed response. I'm impressed by your direct approach and the innovative ideas in your proposal. I'd like to set up a meeting next week to discuss potential collaboration. Does Tuesday at 2 PM work?
Acceptance #2.
I sat in my car, coffee-stained and confused. Two swings, two hits. This was not going according to plan.
That evening, I called Mike for our first official check-in.
"So let me get this straight," he said after I'd recounted the coffee shop incident. "You tried to get rejected twice, and instead you got a date and a major business meeting?"
"I know. I'm terrible at this."
"Or," Mike suggested, "maybe you're learning something important. What if the thing that's been holding you back isn't that people will say no? What if it's that you've been so afraid of rejection that you never gave them the chance to say yes?"
I stared at my rejection journal, where I'd just finished writing up the coffee shop story. In the Lessons Learned column, I'd written: Sometimes the fear of rejection is scarier than actual rejection. Also, watch where you're walking.
"I still need to find a way to get rejected," I said. "That's the whole point of this experiment."
"Then aim higher," Mike suggested. "Ask for things you're sure people will say no to. And David? Maybe stop checking your phone while walking."
After we hung up, I opened my laptop and started researching. If easy requests were getting yes responses, I needed to up my game. I made a new list:
- Ask for a 50% raise (current salary increase request: 3%) - Request to speak at TED Talk - Apply to join exclusive country club (annual fee: my entire savings) - Ask famous author to mentor me - Request free first-class upgrade on every flight - Pitch book idea to major publisher - Ask for corporate sponsorship for personal project - Apply to join board of Fortune 500 company
These felt properly rejection-worthy. These felt impossible.
I went to bed that night with a coffee-stained shirt in my laundry basket, a date with Jennifer scheduled for Friday, and a business meeting that could change my career on the calendar.
Rejection Count: 1 Acceptance Count: 2
Clearly, I had a lot to learn about getting told no.
The next morning, I walked into my boss's office with a printed proposal. "I'd like to discuss a salary adjustment," I said, placing the document on his desk. "I'm requesting a 50% increase based on my contributions this year."
He looked at the number. Looked at me. Looked back at the number.
"Is this a joke?"
"No, sir. I believe my work merits this level of compensation."
What followed was the most uncomfortable fifteen minutes of my professional life. By the end, I had been rejected (obviously), lectured on realistic expectations, and warned about my "concerning" behavior.
Rejection #2. Emotional impact: 8/10.
Now we were getting somewhere.
# Part II: The Learning Curve