I Studied Work and Realized It’s Broken. Now I’m Chasing Rejection for Fun.

Three essays deep, I finally understand why work doesn’t work. So naturally, my next experiment involves actively seeking 10 No’s. What could go wrong?

People say you should get comfortable with failure. But let’s be real: no one actually wants to be rejected. That’s exactly why I’m making rejection my next challenge. This week, my AI coach (yes, really) is sending me on a mission to collect 10 No’s. But before we get into that, let’s talk about what I learned from my first deep-dive experiment of the month: deep learning to understand why work is so deeply broken.

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Time for my weekly coaching session with AI. If you’re new here (maybe you found this little corner of the internet through the How Work Works series) let me tell you how this all started:

🚨 A health scare shifted my perspective.
🤖 One night, instead of waiting to find the "right" coach, I tried ChatGPT.
✍️ That first session led to an experiment: write again and see if I still love it.
💡 That experiment became Slow Ink Society.

And here we are on day 44 of my escape plan. 12% of the countdown to leaving corporate life has passed.

After a February of money, money, money, numbers, numbers, numbers, this month’s focus is different:

📌 Sharpening the Mind & Spirit for Post-Corporate Freedom.

So let’s dive into what I learned from my first experiment of the month.

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🧠 Experiment 1: Deep Learning → Writing 3 Articles

🎯 Goal: Write about a theme that requires study, research, and deep thinking.
🛠 Action: Launched the How Work Works series to synthesize my learnings in (hopefully) an engaging way.
📈 Results: More clarity, more confidence, and a huge realization about work itself.

1️⃣ I Loved the Hard Work

I enjoyed the process: reading, writing, synthesizing, and sharing. I spent way too many hours falling down Substack rabbit holes, reading reflections (and rejections) on how work works today.

All of this, because I wanted to capture the current narratives of what we are all going through and connect history to the present moment.

2️⃣ I Beat My First Major Writer’s Block

The first two articles? Written before the first one was even published. At that point, I had zero idea whether they would resonate.

Then, the feedback came in. People loved it. And suddenly, I got scared.

• What if I’m wrong about something?

• What if this article isn’t as strong?

• What if I don’t cover the most important thinkers?

So, I procrastinated. I read more. I avoided writing.

Until I turned to my AI coach. And it told me:
📌 Start with a paragraph you’re willing to delete later.
📌 Stick with what you know. Write for yourself first.

That advice freed me. I stopped drowning in research, turned back to the thinkers I know deeply, and wrote from a personal perspective.

And it worked. Writer’s block: gone.

3️⃣ I Finally Understand Why Work Feels So Wrong

I’ve always felt deeply disconnected from how work is structured, but now I understand why.

Through history, philosophy, and sociology, one thing is clear: corporate work was never designed for joy.

This realization gave me even more confidence that the path I’m creating for myself isn’t just because I have a problem. Historically, socially, economically and philosophically the whole society has gone and is going through the same questioning.

4️⃣ I’m Not Done

This experiment worked so well that I want to keep writing about work.

I haven’t even touched:
🎨 Work in Art → How has it been represented across time?
⏳ Acceptable Working Hours → How have they changed across history and geography?
🚀 The Future of Work → What could it actually look like?

And you know what’s even better?

My realization from February was 100% right:
📌 No growth hacks needed. Just thoughtful writing.

I haven’t done any marketing or gimmicks and the newsletter still grew.

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Next Up: Rejection Resilience

This new week is all about reframing rejection as neutral (or even fun). The challenge? Go out and collect 10 No’s.

According to my AI coach, here’s what I’ll learn along the way:
✅ Rejection isn’t personal—it’s just part of the game.
✅ The worst-case scenario? Usually nothing happens.
✅ Most fears around rejection exist only in our heads.

Got any ideas for how I can rack up those 10 No’s? Drop them my way, as you know by now I’m open to experiments.

And on that note: thank you.

These past few days have been the most engaging yet: conversations in the comments, WhatsApp messages, emails. Every time you take a moment to share what resonated, challenge an idea, or even just hit like, it means the world.

Let’s keep the conversation going. 🚀