AI Transforms Each Worker Into a One-Person Business
From Substack creators to traditional middle managers, professionals across industries are turning into Solo Chiefs. As a single wringable neck, they orchestrate AI tools and automated systems with ever-smaller teams of humans.
Work has converged before, but never like this.
For most of the twentieth century, work converged around a building. Millions of workers shuffled out their doors each morning toward a designated location where productivity was supposed to happen by virtue of everyone showing up. Time got the same treatment. The 40-hour workweek flattened wildly different professions into a single, standardized cadence. Everyone in the same place, everyone on the same clock.
Accelerated by Covid-19, these convergences have been crumbling. Remote work, hybrid arrangements, gig work, fractional work—all of it has blown apart the fiction that value creation requires physical co-presence or synchronized schedules. Work is becoming distributed, asynchronous, and individualized. We're swinging back to an older norm where work bends around people's lives instead of the other way around.
But this age of work-life divergence is producing a new kind of convergence.
Across industries, roles, and employment models, more and more people find themselves accountable not just for executing tasks, but for designing, coordinating, and steering entire work systems. Tools, collaborators, workflows, priorities—all of it increasingly lands on the shoulders of one individual: the single wringable neck.
Tools, collaborators, workflows, priorities—all of it increasingly lands on the shoulders of one individual: the single wringable neck.
Out of this confluence emerges a new type of worker: the Solo Chief.
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The Creator as Solo Chief
Let's start with the content creators: Substack writers, podcasters, bloggers, vloggers. For years, this work lived in the scrappy hobbyist zone. One person writing, recording, publishing, promoting. Maybe a scheduling tool. Maybe a freelance editor when things got desperate. The ceiling was determined by how many hours you could stay awake and still form coherent sentences.
AI obliterated that ceiling.
Today, serious creators operate with an invisible staff. AI agents research topics, outline drafts, edit audio, generate visuals, translate content, optimize headlines, repurpose posts across platforms, and analyze what actually resonates with audiences. What used to require a small media company now runs through a carefully assembled stack of digital workers.
The creator isn't "doing everything" anymore. They're deciding what gets done, in what order, and to what standard. They design workflows, supervise output, and make any judgment calls that the machines can't. They're not merely scaling themselves; they're orchestrating entire systems.
Creators have become the Solo Chief of their business.
The Entrepreneur as Solo Chief
Or take entrepreneurs, that allegedly rugged breed of risk-takers.
For decades, the startup challenge came with a mandatory checklist: balanced founding team, complementary skill sets, relentless hunt for venture capital. One person was never enough. You needed a technical co-founder, a business lead, a product manager, a growth hacker, and a pitch deck polished until it could cut glass.
That model is quietly collapsing.
Today, single founders are building, testing, and launching products on their own terms. Vibe coding tools let them explore ideas at speed. No-code and low-code platforms turn prototypes into actual products without waiting for a dev team. AI handles research, copy, customer support, and iterative A/B-testing. Bootstrapping replaces fundraising, at least until someone has shown there's a real business with proven product/market fit to fund.
These founders aren't smaller versions of traditional startups. They're something else entirely—operators who design the system, direct the tools, and decide when to scale and when not to bother.
They call themselves solopreneurs. Functionally, they're Solo Chiefs.
The Intrapreneur as Solo Chief
And corporate walls don't keep this pattern out.
Within large organizations, intrapreneurs are experiencing the same shift. Traditionally, launching something new from within an enterprise required permission, budget, and headcount. You needed a formal project, cross-functional teams, steering committees, and months of alignment theater before anything consequential could happen. Innovation was a group sport, heavily supervised and painfully slow.
That logic is breaking down faster than most executives realize.
Today, a single employee can explore, prototype, and validate a new product or service with minimal institutional support. AI tools cover research, customer discovery, design, copy, and testing. Internal data is easier to wrangle. Low-code platforms turn ideas into working demos without waiting for IT tickets to age like bad wine.
The intrapreneur's role shifts accordingly. Less time coordinating people through endless meetings. More time orchestrating systems that actually produce results. The individual becomes the point where strategy, experimentation, and execution collide.
The intrapreneur might still sit within a hierarchy, but functionally they operate like a small organization of one.
In other words, a Solo Chief.
The Business Unit Manager as Solo Chief
Even the supposedly "traditional" roles are mutating beyond recognition.
Take business unit managers. On paper, they've long carried P&L responsibility. In practice, that responsibility was wrapped in layers of constraints: centralized functions, rigid processes, approval chains, shared services, brand rules, budgets decided three levels up. Sure, they were accountable, but they were rarely autonomous.
AI changes the competitive pressure entirely. These same business unit managers are now expected to compete with solopreneurs and small startups that look and behave professionally from day one. Marketing, analytics, customer support, even product development—none of it requires large teams or corporate infrastructure anymore. The external benchmark has shifted, and internal processes and checklists no longer land with anyone who matters.
To keep up, these managers must operate with fewer people, faster cycles, and looser dependence on headquarters. They assemble their own tool stacks, automate aggressively, and redesign workflows around outcomes instead of roles and org charts.
The job of the business manager quietly transforms. Less management of people, more orchestration of capabilities.
Whether they like it or not, they're becoming Solo Chiefs.
The Middle Manager as Solo Chief
The final example might be the greatest irony. The role that was never supposed to be autonomous is steadily becoming exactly that.
Middle managers have traditionally lived inside the tightest part of the organizational corset: the matrix structure. Reporting up, sideways, diagonally. Translating strategy into execution, execution back into slides, absorbing pressure and pushback from every direction. They were coordinators by necessity, not by choice, and definitely not by preference.
Now, enterprises are flattening structures and cutting management layers with remarkable enthusiasm and little self-awareness about what that actually means. The managers who still remain inherit broader scopes, sharper targets, and less support. The mandate is brutally clear: deliver more, faster, with higher quality, more automation, and … of course … fewer people.
What lands on their desk looks suspiciously like a full business. Priorities, resources, delivery, stakeholders, tooling, outcomes—all tied to one accountable individual: the single wringable neck.
To survive, these managers can't rely on hierarchy or headcount. They must design systems, automate relentlessly, orchestrate work across tools, vendors, and machines. Soon, AI isn't optional anymore. It will be the difference between drowning and floating.
Happily or reluctantly, the middle manager is turning into a Solo Chief.
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The Greatest Convergence: the Solo Chief
So here we are, watching business history repeat itself in a new costume.
Work keeps oscillating between convergence and divergence. For several years, we've been loosening the grip on place and time. Offices became optional, schedules negotiable. A real gain, worth defending, and one I have no intention of romanticizing away. But freedom in one dimension rarely comes free. It usually shows up elsewhere as a new accountability.
Across roles and sectors, the pattern is identical. Expectations rise while headcount shrinks. Automation accelerates. AI, software, and robots quietly absorb tasks that once justified entire teams. What remains is accountability: someone still has to decide and prioritize, connect the dots and own the outcomes.
More often than not, that someone is a single person, a single wringable neck—one individual orchestrating tools, agents, vendors, systems, workflows. Managing the work of a small organization. The Solo Chief.
In the age of AI, we're all trapped in the Red Queen Race: doing more, achieving more, with fewer brain cycles and less reliance on wetware, just to keep pace with everyone else who's doing the same. We all find ourselves orchestrating a plethora of workflows while trying not to get entangled and choked by our own automated systems.
This isn't a temporary phase or niche phenomenon. It's a structural shift in how work gets organized, executed, and evaluated. Whether you create, found, manage, or execute, the job increasingly looks the same.
You are the system designer and the bottleneck and the final authority. You're accountable for everything but in control of nothing, except your own work and your ability to orchestrate well. You are the Solo Chief.
You are the system designer and the bottleneck and the final authority. You're accountable for everything but in control of nothing, except your own work and your ability to orchestrate well. You are the Solo Chief.
And that convergence—that shared condition across every role—might be the most significant shift in work since we all agreed to show up at the same building every morning.
Welcome to the age of the Solo Chief.
