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Maps and models for Solo Chiefs navigating sole accountability in the age of AI.
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You’re the single wringable neck—sole accountability, all the fun and all the pain
This is a newsletter for solo chiefs carrying sole accountability: get strategic maps for AI orchestration, decision-making, and systems thinking when you’re the only one responsible.
A while back, I published a piece called The Solo Chief. It named something that had been crystalizing across every sector I watched: an entire class of workers finding themselves solely responsible for outcomes that used to require whole departments.
Creators masquerading as one-person “media companies.” AI-assisted solopreneurs building products with no co-founders. Intrapreneurs launching initiatives inside organizations all by themselves. Middle managers handed sole P&L responsibility while their teams get downsized and their targets get upsized.
Different job titles. Same fundamental condition: you’re the single wringable neck.
I called them Solo Chiefs. The reaction among readers told me I’d hit something real.
But naming a phenomenon and actually helping people navigate it are entirely different projects. So let me be direct about what this publication is about and why I’m the one writing it.
What The Maverick Mapmaker Actually Is
This is a newsletter for Solo Chiefs who need to make better decisions when they only have themselves to blame.
Twice a week, more or less, I publish essays that live in the space between Silicon Valley hype and apocalyptic hand-wringing. You won’t find breathless declarations about AI saving civilization or performative angst about robots stealing your livelihood. Just clear-eyed thinking about how work is actually changing and what that means when you can’t delegate the hard calls.
I offer maps, not recipes.
Maps show terrain. They help you orient yourself, spot hazards before you walk into them, identify possible routes forward. But they don’t dictate your exact path, because your situation isn’t copy-pasteable from someone else’s LinkedIn post. Recipes promise certainty if you just follow the steps. Maps promise clarity about the landscape. I’m in the clarity business, not the certainty racket.
“Maps show terrain. They help you orient yourself, spot hazards before you walk into them, identify possible routes forward.”
The core territory I explore:
AI orchestration — not the shallow “10 ChatGPT prompts to boost productivity” nonsense, but actually designing systems where humans and machines collaborate without you becoming the bottleneck or a glorified prompt monkey
Decision-making under sole accountability — when there’s no committee to diffuse responsibility and no boss to escalate to
Systems thinking for individuals — how to redesign your work instead of just grinding through it
The future of work and organization — separating actual shifts from LinkedIn influencer noise
Managing cognitive load — surviving the weight of sole accountability without surrendering the autonomy that makes it worthwhile in the first place
Why I’m The One Writing This
I’ve spent twenty years thinking about how work gets organized and how we could organize it better. Which is a polite way of saying I’ve spent two decades irritating people who prefer that things stay exactly as they are.
I’m also a solopreneur, serial solo founder, serial intrapreneur, and former middle manager whose head was always on the block. For thirty years, I’ve been the one person that everyone else could rightfully blame. And I happily signed up for that.
I got six books on the subject. Over 150,000 copies sold. More than a thousand speaking gigs across five continents. Built a global community around Management 3.0. Annoyed Silicon Valley techno-optimists and crusty Agile fundamentalists in roughly equal measure. I’ve burned so many conventional bridges that I had to build my own road.
Now I’m running a one-person, AI-orchestrated business—writing, advising, building tools—while attempting to practice what I’ve been preaching all along. This publication is where I think out loud about what’s actually working, what’s failing spectacularly, and what I’m still figuring out in real time.
I’m not an AI researcher with a PhD and a grant. I’m not a futurist with a crystal ball and a TED talk. I’m a practitioner who’s been obsessed with organization design and ways of working for several decades and who now finds himself navigating the same fundamental shift as everyone else.
That’s the angle: not “here’s what the experts in their ivory towers say” but “here’s what I’m learning while building in the trenches.”
The Questions I Keep Circling
This publication doesn’t have a fixed curriculum or a structured course outline. It has recurring questions—the kind that don’t have final answers but get sharper and more useful the more you wrestle with them:
How do you actually lead when your “team” includes AI agents as much as humans?
How do you stay viable as an ind