How to thrive as an Expert Generalist in the age of AI
A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.
Specialization is for insects.
— Robert A. Heinlein
When I read a recent article about Expert Generalists on Martin Fowler’s blog, I immediately changed my LinkedIn title. Finally, someone had named what I’d been doing for 27 years without realizing it!
Here’s why this matters to you, right now: In the age of AI, being an Expert Generalist isn’t just nice to have—it’s your career insurance policy.
The AI paradox nobody’s talking about
While people are panicking about AI supposedly taking their jobs, they’re missing the plot twist: AI is making humans more important—especially those who can see the big picture and guide AI toward what matters most.
Think about it. AI excels at narrow, well-defined tasks. But who decides which tasks matter? Who spots the connections between disciplines? Who asks the questions AI doesn’t ask?
As Ethan Mollick points out in The Cybernetic Teammate, AI can now give individuals the power of an entire team of specialists. But someone still needs to be the conductor of that orchestra.
That someone is the Expert Generalist.
The bridge only you can build
In the early days of cloud computing, I faced a roomful of enterprise executives who kept asking the wrong questions. They wanted SLAs, penalty clauses, unlimited liability—all the contractual safeguards they’d use with traditional outsourcers like IBM.
But cloud isn’t outsourcing. My background in traditional infrastructure, cloud architecture, and a bit of psychology (thanks, Robert Cialdini) helped me realize what they really wanted: control.
So I reframed the entire conversation. “Cloud isn’t a service provider you need to keep on a leash,” I explained. “It’s powerful, remote-controlled infrastructure. And with great power comes great responsibility.” By showing them how cloud gave them more control through automation—not less because of contracts—everything changed.
Making this connection required seeing the whole system: technical, business, and human.
The hidden path from specialist to Expert Generalist
Here’s the thing: every specialist is sitting on a goldmine of transferable principles.
My former expertise in Solaris, ZFS, and SPARC microprocessor architecture might seem obsolete today. But those “narrow” subjects taught me universal principles: systems design, storage architecture, distributed systems, out-of-order processing pipelines. These fundamentals later resurfaced in cloud storage, GPU computing for AI/ML, and modern cloud architecture.
The trap isn’t specialization itself—it’s thinking your knowledge is limited to one domain. The most experienced specialists naturally evolve toward Expert Generalist thinking as they recognize these deeper patterns.
Building an antifragile career
In Antifragile, Nassim Taleb tells a story about taxi drivers being more resilient in their jobs than corporate employees. When business is bad, taxi drivers naturally adapt to changing business conditions and simply pick a different neighborhood. Corporate employees? They get laid off.
I experienced this firsthand. When I left Oracle for AWS in 2012, my former colleagues saw my move into cloud computing as risky. A year later, Oracle announced another round of layoffs. I like to think my flexibility and willingness to explore a new field altogether helped me actually reduce job risk.
Expert Generalists build antifragility into their careers. We don’t just survive change—we thrive on it.
The hidden costs (and why they’re worth it)
To be honest, being an Expert Generalist isn’t always easy.
You never quite fit in. My job titles never really reflected what I did. As a “Solutions Architect” at AWS, I was doing completely different things every year—different expertise areas, different customer verticals, different challenges. Great for someone who loves variety, tough for someone who wants clear expectations.
You plant seeds you may never see bloom. Years after a Big Data workshop I gave, I ran into a customer at a conference. “That workshop changed everything!” they said. “We built an entire ML team and revolutionized our cyber-defense.” As an Expert Generalist, you point others in the right direction but rarely see the fruits of your labor.
Your imposter syndrome will be constant. When you see how vast each field is, you’ll always feel like you don’t know enough. But that humility keeps you learning.
The turning point
Early in my career, I dreaded annual goal-setting. Instead of picking a narrow track, I explained my approach to my then managers as a three-step, repeating cycle:
- Find cool things
- Learn as much as possible about them
- Help customers with what I learned
Initially driven by ”ooh, shiny!” moments (like 3D graphics at Sun), I gradually learned to balance passion with market needs. From 3D chips to microprocessors to HPC to server architecture, enterprise operating systems to Web 2.0, the relevance of what I learned grew. When I discovered cloud computing in 2008, I organized Munich’s first CloudCamp—combining my technical knowledge, community-building skills, and employer resources.
Little did I know my future AWS manager was in that audience. Bridge-building creates unexpected opportunities.
The Symphony advantage
As Dan Pink predicted in A Whole New Mind back in 2006, the future belongs to those who master six essential aptitudes: Design, Story, Symphony, Empathy, Play, and Meaning.
Symphony—the ability to see connections and patterns across disciplines—is the Expert Generalist’s superpower. Like when I helped automotive executives realize they were treating every decision like an irreversible “one-way door”, paralyzing their organization. That insight came from understanding systems thinking, enterprise organizational patterns, and Amazon’s Leadership Principles.
Being an Expert Generalist doesn’t mean abandoning depth for breadth. It means:
- Deep expertise in fundamentals that cross boundaries
- Multiple areas of genuine depth (the many-legged “T” shape)
- The meta-skill of learning new domains quickly
- A sense of knowing when to dive deep on your own and when to collaborate
As Martin Fowler’s article notes, teams need both Expert Generalists and specialists working together. We’re orchestrators, not soloists.
The future needs bridge-builders
Organizations are drowning in silos that can’t communicate. Projects fail not because of technical problems, but because nobody sees the whole system.
I’ve run countless innovation workshops where executives from different departments met for the first time. My role boiled down to helping them see how their decisions ripple across the entire organization. When they realize they’ve been treating their company like separate islands instead of an integrated system, transformation begins.
Expert Generalists are the antidote to organizational blindness. In a world of increasing complexity, that’s not just valuable—it’s essential.
Your journey starts here
Before you think “this only works for privileged tech workers”, consider this: Harrison Ford was a carpenter on the Star Wars set before becoming an actor. The world is full of Expert Generalists from every background—from Benjamin Franklin (printer turned inventor-diplomat-scientist) to Mayim Bialik (neuroscientist, “Big Bang Theory” star, author, podcaster) to Bruce Dickinson (heavy metal singer, airline pilot, fencer).
The principles of building bridges between disciplines work whether you’re connecting cloud with business, acting with neuroscience, or airplanes with rock concerts.
So how do you start building your Expert Generalist capabilities? How do you create a career that’s antifragile, fulfilling, and genuinely valuable?
Choose a subject. Learn as much as you can. Build bridges. Repeat.
This flywheel spins faster with each revolution, as your accumulated knowledge makes learning new domains easier and bridge-building more natural.
Here’s your homework:
Make a list of all your skills and areas of expertise—everything from your formal education to your hobbies. Don’t filter. Include that photography course, your knowledge of Italian cooking, your experience with Excel macros, your understanding of your kid’s school system.
Look for patterns and connections. What principles unite your diverse knowledge? What problems could you solve by combining skills others see as unrelated? Where might your unique combination of experiences provide unexpected value?
This exercise isn’t just self-reflection—it’s the first step in seeing yourself as more than your job title.
The good news? If you’re reading this thinking “finally, someone put a name to what I’ve been doing,” you’re already on the path. If you’re thinking “I want that,” you’re ready to begin.
What connections could you make between your different areas of knowledge that nobody else can see?
That’s where your journey as an Expert Generalist begins.
Want to dive deeper into becoming an Expert Generalist? I’ll be sharing more insights, including my framework for choosing what to learn next. Follow me on LinkedIn, Bluesky, or subscribe to my RSS feed to continue the journey.