03/06/2026
Three months ago I walked away from a job, a business, and a version of myself I’d been holding onto for years. And what I didn’t expect? Slowing down would be the hardest thing I’ve ever done.
In this video I’m talking honestly about what I’m calling my mini retirement — or maybe my midlife awakening — this strange, uncomfortable pause between who I was and who I’m becoming.
I’ve been working since before I was legally allowed to. I’ve worn so many identity labels — the business owner, the podcaster, the regenerative guy, the keto guy. I even used to change my Instagram handle every time I took on a new one. But underneath all of that... where was Ray?
This is what I’m sitting with right now:
The millennial hustle culture hangover — why doing nothing feels like failure
The “messy middle” — a concept from Sarah Wilson’s book I Quit Sugar that hit me hard
Monkey branching in business — and why I’ve finally let go of all the branches
The cup metaphor — it’s not just about refilling it, it’s about understanding the cup itself
What I’m learning as an Enneagram Type 2 about filling others up while quietly running dry
This series — Becoming Raymond Milidoni — is my own documentation. Getting stuff out of my head and into the world. If you’re in a similar season of life, I hope it lands.
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