Why I Made the ‘Chapters’ Video Series
I have been doing a lot of sitting still lately.
Not the anxious kind. The intentional kind. The kind where you actually let thoughts settle, rather than chasing the next thing before the current one has had a chance to land.
That is what a career pause does when you let it. And I have been in one since February, when I left my last role at Seriously Good Design and decided not to walk straight into another.
I wanted to spend my time thinking about who I am. No distractions, just Ray.
And out of that stillness came this question: what have I actually been doing with my life?
Not in a gloomy way. In a genuinely curious way. Because from the inside, a life can look like a series of random events. Businesses that worked, businesses that did not. Projects that felt aligned, and projects I stuck with long after the alignment had gone. Chapters that seemed disconnected at the time, but now, looking back, I can see that they carried a common thread.
That is why I made the “Chapters” video series. To find the thread.
I am recording these videos with no script and no agenda beyond this: what do I actually remember about each chapter of my life, and what did it teach me?
What came out surprised me.
Not the facts. I knew those. Dates, companies, projects, places. But the meaning underneath them. The patterns I could only see by zooming out far enough to look at them all together.
There is a chapter about being a kid in Melbourne who just wanted to matter. There is a chapter about building a web design business at 16 because it felt natural, not because someone told me to. There is a chapter about arriving in the corporate digital world and realising, slowly, that doing something well is not the same as doing the right thing.
Each one of those chapters had a lesson. And I did not always understand it at the time.
Watch the first chapter here: https://youtu.be/K0hu74sMcpc?si=CK_Phz1e2ik3iobY
The middle of the series is where things get real for me.
There is a chapter I keep coming back to. The one about Farming Secrets and the Soil Learning Centre.
Around 2020, I started working with a company called Farming Secrets. At the start, it was another digital role. Helping with content, email, courses, community. But the subject matter was different. It was soil. Regenerative farming. The science of what happens underneath the surface of the earth when you stop treating it like a factory floor and start treating it like a living system.
I remember reading things that stopped me mid-sentence. The connection between soil health and gut health. The parallels between depleted soil biology and depleted human energy. The way a healthy, living soil self-regulates, self-heals, and produces abundance without needing to be forced.
I was not just learning about farming. I was learning about everything.
That chapter was where something cracked open in me. Where soil stopped being a subject and started being a mirror. Where I realised that the same extractive thinking that had degraded the land was the same thinking I had been applying to myself, always producing, always optimising, always running toward the next thing without stopping to ask whether the ‘soil’ was still healthy underneath.
That shift changed everything about where I wanted to point my life next.
Watch the Farming Secrets and Soil chapter here: https://youtu.be/ZLI9yHwsqjo?si=PntS4D7iGQqx4GQ3
One of the unexpected gifts of making these videos was the way they changed the way I think about failure.
There are businesses in my timeline that did not work. Ventures I poured time and money into that ended without the outcome I wanted. And for years, I carried those as quiet evidence of some deficiency in me. Not loudly. Just as background noise.
Making these videos, I had to actually sit with those chapters and talk about them out loud. And what came out was not regret. It was gratitude.
Every chapter that did not go the way I planned gave me something I could not have got any other way. A skill. A contact. A lesson. A calibration. Something that quietly went into the kit bag and came with me into the next chapter, even if I did not know it at the time.
I am 40 now. And when I sit with the full arc of what I have done, I do not see wasted years. I see a person who has always been trying to figure out how to do something meaningful, who has taken wrong turns and got back up, and who is only now beginning to understand the whole picture.
That is not failure. That is becoming.
There is also something about this particular moment in history that I want to name.
We are living through a period of radical change. AI is accelerating the pace of almost everything. Tasks that used to take days are getting done in minutes. The question is not whether things are going to speed up. They already have. The question is what we do with the space that it creates.
Do we fill it with more busyness? Do we cram twenty tasks into the hour that used to hold two? Or do we use it to do something harder and rarer, like actually thinking, reflecting, creating something with depth, or just being a person for a while?
I think we are at a genuine crossroads. And I think the choice matters more than most people are stopping to realise.
Making these videos was my small version of choosing the slower lane. Of deciding that my story deserved more than a highlight reel. Of saying out loud: I have lived a full and strange and interesting life, and it is worth taking the time to understand what it has been trying to teach me.
You can follow the series on YouTube here: https://www.youtube.com/@RayMilidoni
If any of it resonates, I would genuinely love to hear about it. Not because I need validation, but because I think the people in these videos are probably the ones I am meant to keep talking to.
This is not a final chapter. It is more like the moment between chapters, where you sit by the window and take stock before you open the next page.
And I think that is the most important place any of us can be.
