Jurgen Appelo
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Rethinking governance for the one-person business in the age of intelligent machines.
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Articles by Jurgen Appelo
Why Do Corporations Still Exist in the Age of AI?
As someone running a one-person business and often collaborating with other independent workers, I cannot help feeling amused when I see large, hierarchical enterprises struggling with artificial intelligence. The traditional firm doesn’t seem fit for the age of hyper-acceleration. Some authors even think multinational corporations are on their way out, to be replaced by networked agentic organizations (NAOs). Is that true? Or is it wishful thinking?
The Ultimate Framework Makes a Comeback
If you’re a leader or change-maker, you’ve probably got a graveyard of failed frameworks and org designs behind you. The scaling model that needed a 500-page manual. The organizational change model that only transformed cash into catastrophe. The agile framework rollout that made everyone busy and nobody happy. You want something that could actually work, not just another method.
Is the Age of AI a Golden Era for Neurodivergent Workers?
Last week, after a keynote I gave in Spain, I chatted with someone in the audience about neurodivergent people in the age of AI. He has ADHD, and he suggested that now might finally be the moment for people with neurodiverse minds to step forward and take charge. An ADHD diagnosis, he argued, might actually be a better fit for environments that demand constant exploration and context-switching. I nodded vigorously.
The Org Chart Is Choking Your Craft
I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. Sometimes you realize you’ve done no actual work today. You attended meetings. You replied to messages.
Building versus Buying AI Agents: Split Your Stack!
When deciding between outsourcing and do-it-yourself, rent the plumbing but keep the memory, logs, and control plane under your roof. When should you outsource the infrastructure for agentic workflows, and when should you build it all yourself? I felt conflicted. For the past year, I’ve outsourced the hosting of every technology that sits underneath my AI agents (with Fibery, Make, Google Drive, and the rest). I want everything running in the cloud, and I’m happy to pay for that.
Life Is Still Analog, Not Digital (For Now)
I sense an interesting paradox of technology. Let me give you some examples. I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month.
Articles, Not Posts, Win AI Citations
Your LinkedIn strategy for 2026 should stop chasing reach and start publishing citable articles that both people and AI can find. Are you sick of LinkedIn carousels and infographics? Join the club. LinkedIn influencers are like CEOs of broadcast stations, fighting over shrinking territory and optimizing their irrelevance. Every piece of LinkedIn advice I’ve read in 2026 tells solopreneurs the same things. Make better carousels. Sharpen your hooks. Avoid AI sludge. Comment more.
16 Second Brain Practices for Solo Operators (2026)
A map of 16 second brain practices to help solo operators remember decisions, recover context, and stop breaking their own systems. Just this morning, I spent several minutes looking for the official documents of the notary. And when I found them, I thought, “Why are they here, for God’s sake?” That was at least the fifth time I’ve been looking for those same documents. Most likely, I’ll be searching for them again next year. Last week I opened a Make scenario I’d built in February.
AI Creates More Businesses, Not Fewer Jobs
Widesizing means AI lets one capable person do what once took a team. The economy isn’t shrinking; it’s fragmenting into smaller, scrappier units. Large tech companies shed people with the same solemn theater used for royal funerals, and half the internet reacts as if paid work itself just fell off a cliff. Yes, Block cuts jobs. Oracle cuts jobs. Amazon cuts jobs. Every week another CEO waves some consultancy’s AI slide deck around and calls it their new strategy playbook.
Your Hyperdrive Advantage
While most people chat with bots, a few solopreneurs run autonomous AI agents that operate their businesses 24/7. That capability gap is your temporary window to build something competitors can’t replicate. You have no time to lose. I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always.
What Human Advisors Can Still Offer
I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. I wrote this piece for class 22 of ScaleUpNation‘s Board Program.
When Software Breaks Your Workflow
Solo operators pay the full cost of endless tool churn themselves. When vendors move the buttons, your leverage collapses back into hand work. I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always.
AI Agent Architecture for Solo Operators: A 3-Layer Stack
I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. Your overnight agentic hackathon is probably not a viable AI agent architecture.
8 Signals for Solopreneurs and Solo Founders
Eight concrete signals that tell you when to stop exploring and commit, or when to abandon execution and pivot to something new. There’s a particular kind of productive-feeling paralysis where you’re working hard, shipping things, and somehow going nowhere. You’re executing, but on the wrong thing. Or you’re exploring, but past the point where exploration is still honest. For years, I ran a company that was constantly half-exploring, half-executing, feeling vaguely but not entirely productive.
How to Build a Personal AI Agent Stack
Here's how I want to become an agent boss: by building and managing AI agents for real value, not meta-content recursion. It’s 4 AM. I’m staring at the ceiling again, and somewhere in the dark I’m doing the mental arithmetic of how many AI-generated playbooks some author on Substack sold this night while I was busy thinking about something more meaningful—and not getting anything done. The Solo Chief is a reader-supported publication.
Autism Is My Superpower—Oops, I'm on the Spectrum
Understanding your weird brain matters more than getting a certificate for it. My classmates were throwing my schoolbag around as if they were playing beach ball until one boy failed to catch it. My bag hit the street, the chocolate milk carton inside it burst open, and I spent the next hour in the changing room using napkins to wipe tears off my face and chocolate milk from my schoolbooks.
Why Solopreneurs Work Better Alone
You suffer the meetings, slackers, and conflicts. The business pockets the gains. Going solo work might be your better bet. ATTENTION: I celebrate the 100th post of this newsletter with a rebranding. The Maverick Mapmaker is now The Solo Chief. Different name, same obnoxious attitude! Some people should not join a team.
The Accelerometer Method
Technostress is a signal, not a disease. Pick one workflow, make it 10x faster, then move on. Are you suffering from technostress? Feeling anxious about the speed of change? Worried you can’t keep up? Good. That means you’re paying attention. You’re not ready for the age of AI if you don’t occasionally think, “My God, last week I was so slow.” When you look back at your earlier professional self and don’t see a snail struggling up the Burj Khalifa, you’re not improving.
AI Is Killing Creative Risk-Taking-And That's a Problem
Mostly, I just embarrassed myself. Occasionally, I struck gold. One of our national newspapers printed cartoons such as Garfield, Peanuts, and Hägar the Horrible, and I thought, “Hey, I can draw. I could do that too!” So I sat down one Sunday afternoon, rapidly produced six three-panel cartoons, and wrote a letter to the newspaper offering them my exclusive artwork and suggesting that I make these funnies for them daily—for a very reasonable fee.
Your Leaders Are Sleepwalking Into the Gorge
More output, less impact. Your company wants acceleration, but all you feel is desperation. You’ve probably seen this. Your executives are suddenly “all in on AI.” They’ve been to a conference. They’ve nodded at a keynote. They now use the term frontier organization in sentences where it has no business appearing. They don’t really understand the tech, but they absolutely understand the vibe. So now your team is “empowered” to use a tightly curated set of tools.
The Slopreneur Problem (and Why We Need Them)
Slopreneurs flood your feed with AI slop and zero critical thinking. But they’re doing exploratory work the rest of us won’t. Here’s how to survive their content (and learn from it). You probably know the type.
AI Raised the Bar for My Keynote Presentations
In the age of AI, building a quality keynote takes longer, not shorter. Strategic orchestration beats automation. Here’s what three days of work looks like. So, what does it take to build a keynote when you’re the only person accountable for every decision … from storyline to slide design to stage delivery? I could fire up Gamma, Canva, GenPPT, or Prezi AI and generate an entire slide deck in seconds. The technology exists. The button is right there. But who wants to sit through that crap? Not me.
Stop Chasing AI Tools
Technostress and FOBO aren’t helping you win. When Google launches 3 new tools tomorrow, your competitive advantage is calmness. So ... Anthropic came out with Claude 4.6 and OpenAI released GPT-5.3-Codex. This came just after a week of hype around Moltbook, the social media platform for AI agents, which followed the Clawdbot/Moltbot/OpenClaw phenomenon, the open source tool that got renamed twice during a coffee break.
The Tragedy of the Agents
The Tragedy of the Agents maps eight stages from human improvisation to machine alienation. Understanding where you are determines whether you keep agency or lose it. Last week I had eight conversations with readers of this Substack. Solo Chiefs, all of them, each carrying the single wringable neck in their own eclectic ways. My goal was to refine the Job-to-Be-Done for my writing: what problems they actually have, what they need, what keeps them up at night. The meetings were genuinely useful.
The Tragedy of the Agents
The Tragedy of the Agents maps eight stages from human improvisation to machine alienation. Understanding where you are determines whether you keep agency or lose it. Last week I had eight conversations with readers of this Substack. Solo Chiefs, all of them, each carrying the single wringable neck in their own eclectic ways. My goal was to refine the Job-to-Be-Done for my writing: what problems they actually have, what they need, what keeps them up at night. The meetings were genuinely useful.
Why Viability Overrides Agility
The agility versus viability comparison exposes a critical blind spot: agile methods optimize for short-term value, not long-term survival. I’m having fascinating conversations this week with solopreneurs, founders, intrapreneurs and other lone managers to better understand their concerns in the age of AI. And there was one thing Peter Bell told me that blew me away. “I want to have a cockroach business.
250+ Terms for the Future of Work
You've been nodding along in meetings pretending you know what "agentic AI" means. This glossary is your cheat sheet. I asked my team of AIs—ChatGPT, Claude, Gemini, and Perplexity—to perform deep research into the terminology around the future of work in the age of AI. What followed was something like a competitive sport. Each model seemed determined to outdo the others, and I ended up with more than 250 terms.
Choose Your Technology Adoption Strategy: When to Migrate
Five migration strategies reveal when to improve your technology adoption strategy and when to wait, helping Solo Chiefs choose deliberately instead of reactively. I’ve wasted an embarrassing amount of time these past few months exploring AI agent technologies. I’ve tested platforms that no longer exist, learned frameworks that pivoted into something unrecognizable, and built workflows on foundations that crumbled within weeks.
AI, Decision-Making & the Future of Work
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.
AI Rewrites the Advisory Playbook
If you're an advisor, consultant, or board member wondering whether AI just made your role obsolete—it didn't. But it did make the old version of it worthless. I lobbed a grenade at McKinsey yesterday. Not because I enjoy picking on consultants (though I’ll admit it has its charms), but because they’re the clearest example of a business model that’s entering its death rattle.
Clean Up Your Data
You're chatting with someone over coffee. Later, you discover they're one of your paying subscribers. You had no idea. 🤦🏻♂️ Imagine meeting someone at an event and when you get back to your hotel, you discover they were one of your crowdfunders. 😣 Imagine recognizing someone’s name and face but being completely oblivious that you’re facing one of your book reviewers. 🤷🏻♂️ I’m sure you recognize the problem. You have no fricking clue who is who.
You Are Worth More Than You Think
Imposter syndrome made me negotiate against myself for years. Then I asked four AI advisors what I was actually worth. The answer changed how I think about compensation. This Substack isn’t my day job. It barely covers caffeine expenses. Like you, I need actual income and somewhere to keep my brain engaged. For fifteen years, I made a living traveling the world, delivering keynotes, running workshops.
How Jobs-to-Be-Done Helped Me Find My Newsletter's Niche
Customers, suppliers, colleagues, shareholders, partners … They’re all looking at you. You are the single wringable neck. And you wouldn’t want it any other way. I gave myself a year to figure out what the hell I was doing on Substack. With two months left on the clock, I finally got clarity. When I landed on this platform (March last year), I gave myself a year to figure out what the hell I was doing. What topics to write about. Which audience to focus on.
The Solo Chief
From creators to middle managers, AI is turning every professional into a Solo Chief—one person orchestrating tools, agents, and entire work systems alone. You're the strategist, the operator, the content engine, and the customer support desk—all before lunch. Nobody hired you for this job. It just... became yours. Work has converged before, but never like this. For most of the twentieth century, work converged around a building.
Calm Down, Doomers. There Is No Sign of Cultural Decline.
Everything looks the same, but creativity isn’t dead. Systems theory reveals why cultural convergence and explosive innovation happen simultaneously. There’s a toxic idea floating through the intellectual corners of the internet. It’s not a meme or a virus, but more like a fatalistic mood: the sinking suspicion that human culture is in terminal decline. Don’t fall for it. The diagnosis is bleak: humanity has run out of creative ideas.
Is the Business Model Canvas Obsolete? AI Says Yes
The Business Model Canvas and its nine hundred clones are on their way out — not because they were bad ideas, but because AI just made all three of their benefits irrelevant. Like many sociotechnical innovations, it started with a good idea. Alexander Osterwalder, a Swiss business theorist and entrepreneur, created the Business Model Canvas as part of his PhD work on business model ontology in 2005.
A Map for Agentic Transformation
Five organizational archetypes reveal where you actually stand on the agentic transformation map—and why maturity ladders are lying to you. Most discussions about agentic organizations sound like bad self-help books: climb the linear ladder, reach enlightenment, achieve organizational nirvana. But organizations aren’t gyms where more reps equal better results. They’re complex, contradictory beasts that laugh at neat progression models.
Why AI Demands Honest Company Values, Mission, and Principles
As AI systems make more decisions on behalf of companies, vague mission statements and meaningless values become operational liabilities that expose the gap between what organizations claim to stand for and what they actually do. More than half of traditional corporate enterprises list “Integrity” as a corporate value. Beautiful. Makes the shareholders feel all warm inside.
AI Will Disrupt Consulting Like It Disrupted Travel Agencies
The consulting industry is heading for the same seismic disruption that transformed travel agencies over the past two decades. My husband’s AI-generated itinerary looked good on-screen: departing from Puno at Lake Titicaca and then driving through Peru’s spectacular southern terrain, with magnificent vistas across technicolor mountains and distant volcanoes.
When Both AI and Human Experts Got My Diagnosis Wrong
After 18 months of failed treatments and contradictory advice, I discovered something shocking: expert hallucination isn’t limited to artificial intelligence. Sometimes, human experts are even worse at seeing what isn’t there. For three years, I was a running machine. 2,500 kilometers per year, 50 kilometers per week … rain or shine. Consistent as the Swiss train schedule. Then, by the end of 2023, my body staged a coup.
The Ten Commandments of Viability in AI
For Solo Chiefs steering through the coming AI implosion: here are ten principles that give you a safe landing. I’ve been here before. In 1999, my first startup caught a brief ride on the dot-com rocket ship. For a few intoxicating months, I was headed for the stratosphere. Then the bubble burst in 2000, my rocket became a fireball, and I found myself free-falling with a parachute that wouldn’t deploy. The landing wasn’t graceful. The current AI boom seems to follow a similar playbook.
How to Cope with Uncertainty About the Future
I stopped making business plans and started building optionality instead. Here's why coping with uncertainty means growing your platform, not your PowerPoints. My accountant inquired about my business plans and revenue forecasts for the next three years. They “needed” this to create the annual reports. Are you kidding?” I replied. “I don’t even know what I’ll be doing next month!” Strategic planning is the business world’s favorite fortune-telling exercise.
Why Startup Playbooks and Business Frameworks Don't Work
You don’t need them until you’ve built something valuable. Not a day goes by without yet another playbook, framework, or roadmap being promoted by yet another author-entrepreneur on LinkedIn or Substack. Methods are like lawyers. They’re all trying to convince you that you need them. The startup industrial complex peddles a comforting lie: that success is formulaic.
Why Autonomous AI Demands Micromanagement
Will the shift to AI agents drag human management back to the dark ages of command and control? Or will it finally deliver on the promise of progress in team empowerment? I have my popcorn ready. AI agents need constant instruction, clear objectives, and micro-management to function. This shift threatens to drag human management back to the dark ages of command and control, potentially undoing decades of progress in team empowerment.
The Truth About Writing with AI (And Why Critics Are Missing the Point)
The reader's experience is more important than the writer's process. Some readers are calling out authors for using AI in their writing. It's all a bit silly because the only thing that matters is the experience. Yes, even those people who think they care about the writing process are just fooling themselves. It's all just reader experience. Do you think I wrote this piece with AI? I'll let you know at the end.
The Truth About Writing with AI (And Why Critics Are Missing the Point)
It's all a bit silly because the only thing that matters is the experience. Yes, even those people who think they care about the writing process are just fooling themselves. It's all just reader experience. Do you think I wrote this piece with AI? I'll let you know at the end. Bring up the topic of AI-assisted writing on Substack or in any writers' Facebook group and watch the pitchforks emerge.
I Started Drawing Maps Because M-Shaped Professionals Will Thrive in the AI Age
In a world where AI is devouring every professional skill, building depth across multiple domains is your best career insurance. The M-shaped professional: Someone with deep expertise in two or more unrelated domains, connected by cross-disciplinary thinking. You may have seen some drawings I posted earlier. Back in my teenage years, my creativity was all about cartoons and computers—until I hit the classic fork in the road. Two passions, one future: drawing or programming. Which one shall it be?
Don’t Panic! - The AI Job Apocalypse Is Coming (But Humans Will Always Have Work)
The greatest cataclysmic event on Earth happened two billion years ago. Our planet teemed with life in ways unimaginable today. Ancient seas churned with organisms that had thrived for eons in a methane-rich atmosphere. These early inhabitants had perfected their existence, efficiently processing nutrients and reproducing in a stable chemical environment that had sustained life since its very beginning. Then something changed.
Don't Panic!—The AI Job Apocalypse Is Coming (But Humans Will Always Have Work)
AI will kill millions of jobs. But eight forces—from creativity to consciousness—guarantee humans will always have work. Here's the evidence. The greatest cataclysmic event on Earth happened two billion years ago. Our planet teemed with life in ways unimaginable today. Ancient seas churned with organisms that had thrived for eons in a methane-rich atmosphere.
Why I Read 4 Hours Daily to Map the Future of Work
The former CEO of Haier read and reflected for four hours every day. He transformed a monolith into 3,000 micro-enterprises. I hope to do the same—and sharing what I find.
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