5 Counter-Intuitive Lessons from a Year of Radical Reinvention
5 Counter-Intuitive Lessons from a Year of Radical Reinvention
What follows are the five most surprising principles from that year-long experiment. They offer a blueprint for building a more resilient, adaptable, and intentional way of living and working.
1. Your Identity Isn't a Job Title, It's an Operating System
The first principle required dismantling the static identity of a job title. Instead of "trainer," I defined myself by a dynamic operating system—a set of principles governing how I function, regardless of context. This 2025 identity was built on credos like, "I live in draft mode—always refining, always shipping, always learning in public."
This reframing provides a powerful model for career resilience. It detaches identity from a specific role, making it adaptable to the complex operational realities of modern work, like being a "bridge between factory, field, and fleet." By focusing on the process of how you work, think, and learn, your identity becomes an engine for growth rather than a label vulnerable to change.
This new operating system wasn't just philosophical; it manifested directly in how I approached professional work, starting with a complete teardown of traditional corporate training.
2. Stop "Doing Training." Start Building "Readiness Engines."
The conventional model of training—a one-time event focused on completion—was rejected in favor of building "readiness engines." This is not an event but a continuous improvement loop, a learning flywheel designed for a single purpose: measurable competence. It is a rigorous, data-driven engineering discipline.
The system is built on the premise of "mission definition before content," ensuring that every component serves an operational goal:
Within this model, competence is proven through observable behaviors, binary go/no-go criteria, and performance metrics. The goal is to achieve standards over vibes—verifiable skill, not just participation.
This shift transforms training from a cost center into a core operational driver. It becomes a system that doesn't just inform people but measurably improves how an organization functions and maintains its standards.
3. Treat Your Entire Life as a Deliberate Curriculum
Passive experience is fleeting, but structured learning endures. The "Life as Curriculum" framework treats all experiences with the intentionality of a syllabus, using the formula: Location → Lesson → Proof. Each place became a classroom for a specific theme, with the work produced serving as proof of learning.
The 2025 curriculum included:
- Gibraltar: The anchor for deep work, systems thinking, and writing discipline.
- Portsmouth: A lesson in transition planning, logistics, and "movement with intent."
- USA: Expansion of career narrative and testing the portability of readiness models across industries.
- Las Vegas: A "living lab" for real-world pressure testing of risk, judgment, and emotional regulation.
This approach turns life into an active, structured learning journey, ensuring that lessons are not just had, but are deliberately integrated and proven through tangible output.
4. Run Your Creative Work Like a "Catalog + Lab"
This model solves a core dilemma for modern knowledge workers: how to maintain authority with a proven portfolio while staying relevant and innovative through public experimentation. It treats creative production as two distinct but connected modes:
The "Catalog": The established, published body of work that acts as a stable foundation of authority—in this case, the 11 books on Amazon.
The "Lab": The space for active experimentation and in-progress builds, where new ideas are developed publicly. Projects included the Moonshot Poker Manifesto, Shift the Agency, The Authenticity Revolution, and the Skyelark memoir universe.
This dual-mode system provides the stability of a finished portfolio while actively encouraging continuous innovation and public learning. It creates a powerful engine for testing new concepts and developing the next generation of work that will eventually populate the catalog.
5. Engineer Your Decisions by Separating Quality from Outcome
Drawn from the Moonshot Poker Manifesto, this principle offers a profound mental model for navigating uncertainty. The core idea is to shift focus from results, which are influenced by luck, to the one thing you can control: the quality of your decisions. This philosophy treats life and business as an engineering problem where good systems and judgment are the goal, because luck is an uncontrollable variable.
This provides immense psychological freedom for any founder, creative, or project manager. It de-risks innovation by decoupling self-worth from market outcomes. When a sound process leads to a poor result, it can be analyzed without drama. As the principle states, Failure Is Data Not Drama. This builds resilience and ensures that learning, not regret, is the primary result of any setback.
What's Your Operating System?
Taken together, these five lessons synthesize into a single, powerful meta-lesson: a radical shift from an identity based on external validation (job titles, project outcomes) to one based on internal, process-driven systems (operating principles, readiness engines, decision quality). It's a move from chasing results to building an engine that reliably produces them.
This entire experiment was rooted in the shift from an external identity to an internal one. It prompts a vital question for anyone seeking meaningful growth:
If you had to describe your own personal operating system in a single sentence, what would it be?