For most of my professional life, I assumed I had a collection of unrelated careers.
Over the years I worked in politics, professional kitchens, construction, technical education, developer advocacy, and technology leadership. More recently, I’ve found myself spending time on institutional memory, provenance, AI architecture, museums, archives, and historical research.
Looking at that list on paper, it feels random. A career counselor might call it a lack of focus. An Applicant Tracking System would almost certainly struggle to figure out what box to put me in.
For a long time, I viewed it the same way. Every career change felt like starting over. Every transition came with the uncomfortable feeling that everyone else had chosen a lane and stayed in it while I was wandering between industries.
It wasn’t until recently, while working on the Sovereign Systems Specification and updating my personal website, that I began to notice something unexpected.
The industries had changed.
The questions had not.
The Same Questions in Different Places
When I worked in politics, information was everything. Every statement, every policy position, and every talking point ultimately came down to a simple question:
“According to whom?”
When I worked in professional kitchens, the same question appeared in a different form. Recipes, inventory, supplier relationships, food safety procedures, and training all depended on knowledge being documented, shared, and trusted. Making the same “house ranch” recipe from memory isn’t the same as having it written in a procedure.
Construction wasn’t much different. Plans, permits, change orders, inspections, and customer agreements all relied on accurate information and a clear understanding of where that information came from. A builder who’s working from memory instead of the stamped plans builds the wrong room. That’s not a rounding error — that’s a tear-out.
Technology brought the same challenges into a new domain. Documentation, system architecture, databases, APIs, observability, and developer education all revolve around helping people understand complex systems and trust the information they are using to make decisions.
More recently, my interests have expanded into museums, archives, historical research, and AI systems. Yet even there, the same themes continue to emerge.
The questions kept reappearing in different forms:
- How do people store knowledge?
- How do they trust knowledge?
- How do they lose knowledge?
- How do they pass knowledge to the next generation?
The technology changes. The industries change. The underlying questions remain remarkably consistent.
A Phrase That Refused to Stay in One Project
While writing the Sovereign Systems Specification, I coined a phrase that I initially thought was simply a good line:
Information without provenance is just gossip.
At first, it was intended as a commentary on AI systems. Large Language Models are increasingly capable of producing convincing answers, but confidence is not the same thing as evidence. If an answer cannot be traced back to a source, its reliability becomes difficult to evaluate.
The more I thought about it, however, the more I realized the phrase applied far beyond AI. Every field where trust matters has a provenance problem.
The phrase kept showing up because the principle kept showing up.
Eventually I stopped thinking of it as an AI concept and started viewing it as a general truth.
Maybe It Wasn’t Several Careers
For years I looked at my resume and saw a collection of disconnected experiences.
Politics, culinary arts, construction, technology, education, and research.
The assumption was that these represented different chapters of my life.
What I’m beginning to suspect is that they were all chapters in the same story.
The industries were different. The tools were different. The job titles were different.
What remained constant was an interest in understanding how knowledge is created, organized, trusted, preserved, and shared.
Seen through that lens, the transitions no longer look quite so random.
Politics was about information and trust.
Kitchens were about process and knowledge transfer.
Construction was about documentation and accountability.
Technology was about systems and understanding.
Museums and archives are about preservation.
AI is forcing us to revisit all of those questions at scale.
The Questions That Follow Us
One of the unexpected benefits of getting older is that you eventually accumulate enough experiences to identify patterns that were invisible while you were living through them.
In your twenties and thirties, careers often feel like a sequence of decisions.
In your forties and fifties, they sometimes start to look more like a sequence of questions.
The jobs change.
The industries change.
The technologies change.
The questions worth asking tend to remain remarkably consistent.
Looking back, I don’t think I’ve spent thirty-five years working in a series of unrelated professions.
I think I’ve spent thirty-five years exploring the same problem from different angles.
And perhaps that’s the lesson hidden inside a long and winding career:
The most important thing you carry from one job to the next isn’t a title, a skill, or a technology.
It’s the set of questions you never stop asking.
That’s the foundation the Sovereign Systems work is built on.
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That’s the foundation the Sovereign Systems work is built on.
for knowing that PyCon 2018 would be held in Cleveland, Ohio. Intel had several drawings for an 
, along with several other vendors actually. 
which I sadly wasn’t able to win.
, or Russell Keith-Magee of 