My professional journey hasn't been a straight line dictated by corporate ladders; it has been an evolution driven by an underlying operating system. I focus on navigating my career through the intersection of curiosity, serendipity, and systemized thinking: aggressively investigating the fringes of technology, leaning into unexpected professional encounters, and treating every lesson learned as data to be religiously documented, tested, and scaled.
When I look back at the inflection points that truly redefined my trajectory, they didn't come from massive, planned corporate shifts. They came from tiny sparks—fringes, anomalies, and small habits that compounded over time.
Here are three moments where this philosophy proved itself in real life.
1. Curiosity: Change Starts at the Fringes
Years ago, long before it became an industry-standard behemoth, I had a brief interview with the GitLab data team. During that conversation, I believe Taylor A Murphy mentioned a relatively obscure open-source tool called dbt (data build tool). It wasn't standard practice yet, and it certainly wasn't a job requirement.
But it was a fringe signal.
Instead of treating the interview as a siloed event, I followed the curiosity. I dove down the rabbit hole, spent days and weeks self-learning the tool, and realized it solved a fundamental flaw in data architecture. Because I tuned my radar to the edge of the industry rather than the mainstream center, every single professional data and analytics role I have held since has been structurally impacted and accelerated by that single exposure. Change always starts at the fringes; your job is to pay attention.
2. Serendipity: Trust the Outliers
Not too far into my career, I spent a brief period working at a company called Lumi under Steph Ango, who is today the CEO of Obsidian. It was a short interaction in the grand scheme of a career, and at the time, the exposure to someone who cultivated deep practice on hyper-granular personal markdown notes might have seemed like an eccentric workflow choice rather than a foundational career pillar.
But I chose to sit with it. I trusted the serendipity of crossing paths with a visionary thinker and adopted my own version of the practice.
Over the years, that habit evolved into a massive, highly structured personal knowledge base. Today, that skillset and workflow exercises a muscle that we can now recognize under the label of "context engineering". Because I leaned into an unexpected encounter that didn't fit a standard career template, I am now able to leverage LLMs in a highly tailored, hyper-creative way that gives me a distinct technical edge. When an outlier crosses your path, don't dismiss it—sit with it.
3. Systemized Thinking: The Power of Working Out Loud
The third pillar is the mechanism that binds the first two together: strict, systemized execution. Influenced during my time at Deutsche Bank by John Stepper and his concept of Working Out Loud, I realized that building in secret is a wasted opportunity.
Treating execution as a broadcasted data stream started early. During down hours at Deutsche Bank, I wrote internal posts on the company intranet sharing my experiments. That habit of documenting out loud directly led to early connections in cryptocurrencies back in 2015.
Later, as an early employee at Finexio—where the entire company could fit in a single room—working out loud became a necessity. In a resource-constrained startup, collaboration is your greatest leverage, but you can only collaborate on what is visible. By bringing our work to the table and systemizing our efforts, we moved faster and solved harder problems together.
Finally, this philosophy underpins my work in open-source software, which is the ultimate expression of working out loud. Actively opening your work to public feedback and criticism can be uncomfortable, even awkward. But that vulnerability is incredibly powerful: it exposes your blind spots, highlights flaws, and uncovers features you might never have imagined on your own. When you systemize your thinking and broadcast it, you turn private effort into compounding luck.
The Blueprint
If you want to build a career that actively captures upside while remaining resilient to technological shifts, operationalize these three laws:
- Follow the Fringes. Mainstream knowledge keeps you average, but the edges of technology hold the future. Cultivate an aggressive curiosity for the emerging tools and ideas that others are dismissing as niche.
- Trust the Serendipity. Never minimize a short-lived project, a brief interview, or an unusual peer. Treat every unexpected professional intersection as a high-leverage seed that could completely shift your trajectory years down the road.
- Systemize and Broadcast. Document your thinking religiously, test your hypotheses like an engineer, and share your work out loud. Aggressive transparency turns private knowledge into compounding organizational luck.