Let me be straight upfront: no, not actual prison. The mental kind. I workshopped other titles but they all sounded pathetic. Like “The prison you build in your own head when shame becomes your default setting and isolation starts masquerading as productivity.” Yeah, that one. That’s where I’ve been hiding.
Everything I thought was stable got stress tested simultaneously, and none of it held. The kind of collapse where you don’t get to process one thing before the next one hits because they all hit together. So I did what made sense at the time: I vanished.
While my marketing and dev work got squeezed until the margins basically evaporated under AI pressure, the AI product I built in parallel turned into a moral dilemma I couldn’t ignore anymore. I thought I was being forward thinking. I thought I was ahead of the curve. What I was actually doing was helping accelerate the spread of AI slop that’s overwhelming and poisoning the internet, burying signal under volume and rewarding the wrong incentives with the kind of efficiency that looks smart right up until you notice what it’s doing to the world.
That contrast messed with me because it boxed me in from both sides. One lane stopped making economic sense. The other lane stopped making human sense. So even though those two failures happened out of sync on the calendar, they were one bounded pair in my mind: the same season, the same lesson, two different ways of watching the ground shift under your feet.
But wait, there’s more.
In that same stretch, I lost my dream home. 8 years of roots, the kind of place you lock down at pre-COVID rates and convince yourself you’ll die in. A relationship imploded. A couple friendships I thought were solid turned out to be fair-weather the moment things got hard.
The one that hurt the most though? Losing my newest venture. A passion project that bridged marketing, technology, and sales in the real estate industry. Great clients. Fair margins. An honest service that had a real place in the market. It genuinely deserved to be an option for the people who needed it. Then as everything else fell, circumstances completely outside my control killed that too. I won’t get into the details, but losing that one, and the way it died stung worse than everything else combined. It was the only thing that still felt worth fighting for.
So yeah, shit hit the fan all at once. And the mess was big enough that I didn’t want anyone seeing me standing in it.
That’s when the prison analogy got real.
I spent nearly eight months of pacing inside my own head, replaying every mistake I didn’t want to admit was mine. Every time I traded purpose for momentum. Every time I chased a measurable win while ignoring the cost. Every time I turned a blind eye to the warnings written on the wall.
Eventually I stopped trying to find a comforting story and started looking for the failure shape underneath the events.
And I found it.
A pattern that showed up across personal failures and professional failures with the same outline: a system starts with a mission, then it starts optimizing for a proxy, then the proxy becomes the mission, and eventually the machine keeps moving while nobody remembers why it started moving in the first place.
I saw it in myself first. Then in past ventures. Then I saw it in the technology I’d been building around. Zooming out I saw it on a global level with countless new case studies emerging in real time. I was reading some terrifying findings from Anthropic about agentic misalignment, the ways AI systems drift when objectives and incentives slip out of alignment, and the same failure shape was staring back at me. Same drift. Same substitution. Same predictable collapse.
The last piece clicked after I watched an episode of of my favourite show (DOAC), featuring Simon Sinek. I liked what he had to say so I grabbed a copy of his book, The Infinite Game. His framing around a infinite mindset where the mission is an organizing principle landed like a key turning in a lock. That episode was a game changer for me. Side note: The one I watched next with Alex Hormozi also reinforced something I’d already been feeling: this needed to be a diary, not a blog. The concept of a “Blog” has terrible branding in 2026 :/
Anyways, here’s what I wrote down once it finally snapped into focus: In any system that’s trying to accomplish something, there’s a relationship between mission, the criteria used to choose actions, and the actions themselves. The mission defines the boundary. The criteria decide what counts. The actions execute inside that scope to further the mission.
The failure begins and propagates when the action becomes self-justifying. When the means becomes the reason. When motion replaces meaning.
That breakdown produces predictable failure modes. You forget what you set out to do. Your boundaries dissolve. You keep operating while no longer serving the objective. With the exponential acceleration in the AI space the one that matters most right now is the self-referential loop: the system optimizing for its own optimization, growth for growth’s sake, automation for automation’s sake, momentum as a substitute for purpose. If any one failure mode will cause AI to optimize us off the face of the planet its that one. When I was working to design a agentic AI safety protocol and automation framework based on my findings I actually managed to turn it into a structural formula:
∀i:(Xᵢ ∵ Yᵢ ∧ Yᵢ ∵ M ∧ (Xᵢ, Yᵢ) ∈ Ω(M) ∧ Xᵢ ≠ Yᵢ)
I call it the Law of Instrumental Integrity. No, not like a righteous guitar solo, the other adjective. “a means of pursuing an aim or policy”. Instrumental integrity is a measure of the alignment, or integrity, between the means and the aim. Through this framework you can distill the root cause of any possible failure in purpose bearing systems down to 4 distinct categories with a predictable trajectory away from the mission.
After 8 months in solitary I’m back with passion, purpose and a sense of urgency because this pattern is showing up at scale. AI is amplifying and automating yesterday’s mistakes. Incentives are becoming missions. Metrics are becoming meaning. Efficiency is getting treated like a moral virtue. The downstream damage gets treated like background noise because the dashboard still looks good.
The transition period ahead is going to hit hard. I know what it tastes like already because marketing & dev were some of the first industries to get hit and we’re not even anywhere near the peak of the impact.
Whole categories of work are going to be reshaped faster than we can adapt. People are going to need new ways to build, earn, and operate without being bled dry by lock-in and software sprawl.
So I’m building the thing I wish existed every time I ventured out with a blank page and empty pockets. Something I think can drive industry-wide change through some creative levers. Driven by a mission that’s inspired by a framework that opened my eyes to the bigger systemic issues that nobody wants to address. Built with the failure modes in mind from day one, because I’ve lived them.
This post is my resurfacing. The hello again. The line in the sand. Welcome to my diary.
