My career has looked all over the place at times.
Honestly, my life has too.
WordPress. Design. Marketing. Operations. Trades. Agency work. Client work. AI systems. Family pressure. Health stuff. Constant rebuilding.
A lot of it probably looked scattered from the outside.
For a long time, I might have seen that as a liability.
Now I think it may be the thing that trained me for this moment.
Because when people say “generalist,” they usually mean something shallow. Someone who knows a little about a lot. Someone curious, maybe useful in a meeting, but not deep enough to trust when the work gets serious.
That is not what I mean.
I am not talking about the shallow journalist version of a generalist. I am not talking about the person who reads a few summaries, picks up the vocabulary, and suddenly has opinions about every field.
When I say I am a generalist, I mean I am broad because my life forced me to be broad.
But I am also deep on the work.
That combination is the whole point.
There is a casual generalist, and there is a deep generalist. Confusing the two is where the whole conversation goes sideways.
Key takeaways
- Generalist does not have to mean shallow. It can mean range built through real work.
- The scattered path was expensive, but it trained pattern recognition across code, design, marketing, operations, trades, and AI.
- AI makes output cheaper, which makes judgment more important.
- Deep generalists can connect rooms that usually talk past each other.
Generalist is too vague
The word “generalist” is almost useless by itself.
It can mean someone with range. It can mean someone without depth. It can mean a person who connects departments. It can mean a person who never stayed with anything long enough to get good.
That is the problem.
People hear “generalist” and bring their own baggage to it.
Some people picture the dilettante: a person with surface-level opinions on everything and earned judgment on nothing. The kind of person who can talk about strategy, design, code, marketing, AI, business, and operations, but cannot actually carry the work when it gets heavy.
I get why people are allergic to that version.
I am too.
But there is another version.
The deep generalist has range, but the range is not decorative. It comes from doing real work across different domains long enough to understand the tradeoffs. It comes from building things, breaking things, fixing things, explaining things, selling things, and living with the consequences.
The distinction is not generalist vs. specialist. The distinction is shallow breadth vs. deep range.
The scattered path was not wasted
This is the part I am starting to understand differently.
My career and life have been nothing short of all over the place at times, but it has served me well in the long run.
Not because chaos is noble. It is not. A scattered path can cost you time, money, focus, momentum, and peace. I am not turning it into a motivational poster.
But when you have lived in enough worlds, you start to see patterns other people miss.
You hear a business owner describe a marketing problem and you know it is really an operations problem. You look at a website and know the issue is not the design, it is the offer. You watch someone use an AI tool and can tell the problem is not the prompt, it is that they do not know what good output looks like.
That kind of judgment does not come from dabbling.
It comes from getting deep enough in enough places that the connections start showing up.
Broad does not mean floating above the work
This is the line I care about.
A shallow generalist floats above the work.
A deep generalist gets dirty.
I have spent years inside WordPress, not reading about it from a distance. I have worked on design, copy, client strategy, operations, systems, and implementation. I have dealt with real clients, real constraints, real budgets, real deadlines, and real cleanup when something did not work.
Now I am in the trades world too, learning work that does not care how clever your abstract thinking is. Plumbing is physical. It has consequences. If you are wrong, something leaks.
That kind of work changes how you think.
It makes you respect reality.
And that matters when you are using AI, because AI can make unreality look polished.
Range only matters if it stays attached to reality. Broad knowledge without hands-on judgment turns into confident noise.
AI makes this more valuable
Dan Shipper had a useful line: models make yesterday’s human competence cheap.
That sounds threatening at first.
But it also clarifies the job.
If AI can execute faster, the bottleneck moves. The valuable skill becomes knowing what should be built, what should be ignored, what is missing, what is wrong, and whether the output fits the real situation.
AI is good at producing.
It is not good at caring whether the production matters.
That is where deep generalists get dangerous.
They can move between layers. They can understand the technical side without forgetting the customer. They can talk to the business owner without losing the implementation details. They can see when the code is fine but the strategy is weak. They can see when the copy sounds good but the offer is muddy.
They know enough about each room to hear when something is off.
Credentials miss this kind of depth
A lot of systems reward narrow depth.
That makes sense. Credentials need categories. Resumes need labels. Companies need job descriptions. Schools need departments. People need some way to sort the world.
But real work does not respect those boxes.
A business problem rarely arrives as one clean category. It shows up tangled. The website is tied to the offer. The offer is tied to the operations. The operations are tied to the people. The people are tied to the incentives. The incentives are tied to the money.
That is why a purely narrow view can miss the actual problem.
Specialists matter. I am not arguing against specialists. Deep expertise is real, and pretending otherwise is stupid.
But the person who can connect specialists, challenge assumptions, and understand enough of each domain to keep the work honest has a different kind of value.
That value is harder to measure.
It is also harder to fake.
The deep generalist is not avoiding expertise. He is carrying expertise across more than one room.
This is not about being interesting
I have always liked the Renaissance man idea.
But that can get romantic fast.
This is not about being interesting at dinner. It is not about collecting hobbies. It is not about sounding smart across a bunch of topics. Nobody needs another person with ten opinions and zero receipts.
The point is practical.
Can you diagnose messy reality?
Can you see the connection between the tool, the customer, the business, the system, and the person doing the work?
Can you use AI without outsourcing your judgment to it?
Can you go deep enough to be useful, then wide enough to connect what other people leave separated?
That is the version of generalist I care about.
The casual version will get exposed
AI is going to make shallow generalists louder for a while.
They will sound more informed. They will produce cleaner documents. They will use better vocabulary. They will have more polished answers to questions they still do not understand.
That is going to create noise.
But over time, the difference will show.
The casual generalist can generate output. The deep generalist can judge it. The casual generalist can summarize a field. The deep generalist knows where the summary breaks. The casual generalist can talk across domains. The deep generalist can build across them.
That gap matters.
Especially now.
What I am betting on
I am not betting on being the smartest person in every room.
That is not realistic, and it is not the point.
I am betting on range plus depth. I am betting on the ability to connect domains without floating above the work. I am betting that the messy path, the weird career turns, the constant rebuilding, and the pressure to figure things out were not wasted.
AI makes execution cheaper.
It does not make judgment cheap.
And the more output floods the world, the more valuable it becomes to know what is real, what is useful, and what is bullshit.
That is where the deep generalist wins.
