I’M NOT QUITTING… I’m ✨ rebranding ✨.

Welcome to Fail Files 👋

Failure. We all hate it. It’s a messy, uncomfortable truth… That can ultimately lead to progress. You can learn so much from failing—sometimes more than from winning. So let’s reframe it together.

Failure isn’t always pretty, and sometimes it’s harmful. But it’s often in those very moments that we learn the most. Even when the failure feels off-track or unjust, there’s usually something we can take away from it.

Failure is essential for growth, even foundational to success.

Each week, Fail Files breaks down a failure that matters. Whether it’s a personal mistake, a systemic collapse, or a business flop, we’ll dig into the lessons that can help us rethink what’s next.

Ready to explore failure and where it can take us? Let’s go!

🤷🏽‍♀️ W T F H A P P E N E D ?

The first failure I’m exploring is… this very newsletter.

When I first launched my newsletter, learnshiv, I was fired up with ideas:
- A Glossary of Growth to explain tech, social justice, and personal development concepts.
- A “Lesson Learned” section where I shared insights every week.
- Free downloads and inspiring profiles.

But it was too much. After a few months, I was scrambling for content and couldn’t even explain what the newsletter was really about. I’d vaguely say, " Future-proof yourself by learning diverse topics,” but it didn’t feel like it all tied together.

It stressed me out every week instead of energizing me. I stopped being excited to share it and started feeling scared that it would not be helpful to my audience.

Worst of all, I had been writing for MONTHS and barely hit 150 subscribers.

Then, I started coaching with a master content marketer, and that’s when everything clicked. I realized I needed to simplify and really explore my purpose.

He helped me clarify my vision:
✔ Teach mental models and frameworks that help people work smarter and live better.
✔ Help people survive the grind so they can thrive.

So, I reframed the newsletter’s mission: "For thoughtful professionals who understand career success and cultural literacy are inseparable."

🧠 L E T ’ S A N A L Y Z E

It felt closer, but something still wasn’t clicking. I wasn’t repurposing my content. Instead of building off what I shared on other channels, I kept reinventing the wheel each week, and it got EXHAUSTING.

I genuinely thought about quitting. Then, a short video I made about failure went somewhat viral—70,000 views. And that’s when it hit me: failure was the throughline I had been missing.

Failure isn’t just personal; it’s systemic. It’s where the lessons live. What if failure became the focus of my newsletter? It’s clearly something the audience resonates with, and it’s a concept that can be applied to many of my interests.

So, welcome to Fail Files. Every week, we dive into failures that matter—from personal screw-ups to organizational collapses—and uncover the patterns, insights, and lessons we can learn.

The pivot feels right. Finding content is no longer a scramble. It feels aligned, purposeful, and, most importantly, sustainable. I’m excited to see how it evolves as I continue to share these real, raw, and essential lessons from failure.

✅ A C T I O N I T E M S

Here’s what you’ll get from this newsletter moving forward:
🟢 A bi-weekly exploration into a failure you can learn from.
🟢 It could be personal, work-related, systemic, or a case study… endless possibilities.
🟢 I’ll explain what the failure is, what we can learn from it, and how we can move forward with purpose.

What do you think?

Thanks for reading our 37th issue. I can’t believe I got here (it only took me three rebrands 😆).

Thanks for reading! 🚀

Remember: failure isn’t the end; it’s a moment to pause, reflect, and evolve. Every breakdown carries the potential for breakthrough, and every failure is an opportunity for growth.

So, what did you learn from today’s failure? How will you use it to move forward, shift your perspective, or take action?

Let us know—your insights are part of the bigger picture. Until next time, keep exploring, keep learning, and keep evolving.

And most importantly, DON’T be afraid of failure, babe; welcome it.

Have a great week,

Shiv 💁🏽‍♀️