Chapter 7

Chapter 7: Midpoint Crisis: When I Almost Quit

6 min read

Day 183. Rejection count: 403. Emotional reserves: Empty.

I sat in my car outside the office building where I'd just been escorted out by security. Rejection #403 had gone spectacularly wrong.

The ask had seemed harmless enough: Could I sit in on a board meeting at a random company to learn about corporate governance? I'd walked into their headquarters, found my way to the executive floor, and politely made my request to the executive assistant.

What followed was twenty minutes of increasingly tense interactions with security, HR, and eventually a very angry CEO who threatened to call the police if I didn't leave immediately.

"This isn't courage, it's harassment!" he'd shouted. "What kind of person just walks into private offices making demands?"

Emotional impact: 10/10.

But it wasn't just this rejection. It was the accumulation. Six months of daily no's had worn me down in ways I hadn't anticipated. The experiment that had initially energized me now felt like a weight I carried everywhere.

My tracking spreadsheet had become a monument to failure. Yes, I'd had unexpected successes. Yes, I'd grown. But I'd also been:

- Laughed at (47 times) - Yelled at (23 times) - Ignored (142 times) - Pitied (31 times) - Threatened (3 times) - Publicly humiliated (16 times)

The cumulative effect was crushing. I'd started the experiment believing I could build immunity to rejection. Instead, I'd just gotten better at functioning while hurt.

I drove home and did something I hadn't done in six months: I went to bed at 3 PM and didn't attempt a single rejection.

The next day was worse. And the day after. By Day 186, I hadn't logged a single new rejection. The streak was broken.

Jennifer found me on the couch that evening, laptop closed, journal untouched.

"How many rejections today?" she asked.

"Zero."

"Yesterday?"

"Zero."

She sat next to me. "What's going on?"

"I think I'm done. I've proved the point. 400 rejections is respectable. Nobody needs to hit 1000."

"Is that what you're telling yourself?"

I looked at her. "That CEO was right. I'm not being brave. I'm being annoying. I'm that guy who makes people uncomfortable for the sake of a spreadsheet."

"One angry CEO doesn't erase six months of growth."

"It's not just him. It's... I'm tired, Jen. I'm tired of being told no. I'm tired of putting myself out there. I'm tired of feeling like I have to earn every single thing by facing rejection first."

She was quiet for a while. Then: "Remember when we met?"

"The coffee shop disaster."

"You were terrified. Shaking. You literally fell on your face rather than ask me out."

"Thanks for the reminder."

"But you were going to ask. After six months of building up courage, you were finally going to do it. That's what I fell for – not the guy who fearlessly collects rejections, but the guy who feels the fear and asks anyway."

"What if I don't want to ask anymore?"

"Then don't. But don't quit because one person made you feel small. Quit because you've learned what you came to learn."

That night, I couldn't sleep. I pulled out my journal and read through six months of entries. The evolution was undeniable:

Day 2: "Sent three emails asking for informational interviews. Took me four hours to hit send. Hands shaking the entire time."

Day 45: "Asked five strangers for their phone numbers. Three said no, two said yes. Whole thing took ten minutes. Getting faster at this."

Day 98: "Pitched book idea to agent at conference. She said no but introduced me to three other agents. Rejection is becoming a networking tool."

Day 156: "Dad and I talked for three hours on our drive to Denver. He told me about his own failures in business. First real conversation we've ever had. Worth every rejection that led here."

The person who wrote that first entry wouldn't recognize the person who wrote the last one. But was that growth worth continuing to put myself through this?

On Day 187, Sarah (the colleague who'd landed Morrison Industries back at the beginning) asked me to coffee.

"I heard about the security incident," she said.

"News travels fast."

"David, can I tell you something? When I got that Morrison account, I was terrified. I'd sent one email on a good day and gotten lucky. Meanwhile, I watched you transform into someone who takes bigger swings in a day than I take in a year."

"And look where it got me. Kicked out of buildings."

"And published in magazines. And speaking at conferences. And dating Jennifer. And actually talking to your dad. Should I keep going?"

"Those aren't because of the rejections. Those are despite them."

She laughed. "You really don't see it, do you? Let me ask you something: If you quit now, what happens tomorrow?"

"I go back to normal life."

"No. You go back to pre-rejection-experiment life. You think you can just turn off six months of momentum?"

She was right. The thought of returning to my old patterns – the drafts folder full of unsent emails, the opportunities ignored, the safe, small life – made me feel sick.

"But I'm tired," I admitted.

"So rest. Make this week about easy rejections. Ask for extra napkins at restaurants. Request songs on the radio. Small stuff. But don't stop. You're past the halfway point. This is exactly when marathon runners want to quit too."

That afternoon, I attempted my first rejection in four days. I asked the barista if I could get my coffee for free.

"Why?" she asked.

"Because I'm having a rough week and I thought it might make me smile."

She looked at me for a moment, then rang up my order. "That'll be $4.50. But here." She drew a smiley face on my cup. "Hope your week gets better."

Rejection #404. Emotional impact: 2/10.

I sat in the coffee shop and opened my laptop. The spreadsheet stared back at me. 404 rejections. 596 to go.

I added a new column: "Days Until Completion If I Average 3 Rejections Daily."

Answer: 198 days.

That felt impossible. But so had 404 rejections, once upon a time.

I called Mike that night for an emergency check-in.

"I want to quit," I said before he could even say hello.

"Okay."

"That's it? Okay?"

"What do you want me to say? That you can't quit? Of course you can. The question is whether you should."

"I got kicked out of a building."

"And?"

"And it was humiliating."

"More humiliating than living in fear of rejection your whole life?"

I had no answer for that.

"Look," he continued, "you've already won. You've proved that rejection won't kill you. You've changed your entire life trajectory. If you want to stop at 404, stop at 404. But don't stop because you're afraid. That's exactly the pattern you started this to break."

After we hung up, I made a decision. I wouldn't quit. But I would adjust. The next phase of the experiment would be different – less about quantity, more about quality. Less about proving something to a spreadsheet, more about continuing to expand my life.

My journal entry from Day 187:

The middle is harder than the beginning. In the beginning, you have enthusiasm and novelty. The middle just has the work. But maybe that's the point. Maybe the real transformation happens not in the excited first attempts or the triumphant final push, but in the messy middle where you want to quit but don't.

Tomorrow I'll try again. Not because I have to hit 1000. But because the alternative – going back to the person I was – is the only failure I can't accept.

Rejection #405 came the next morning. I asked the CEO who'd had me escorted out if he'd be willing to have coffee and let me apologize in person.

His assistant email: "Mr. Davidson appreciates your apology but declines your invitation. He suggests you might benefit from understanding appropriate professional boundaries."

Fair enough. But I'd asked. And I'd survived.

The middle wasn't over. But I was still in it.

One rejection at a time.

# Part III: The Transformation