Jack of All Trades, Master of Something

... for there is an upstart Crow, beautified with our feathers, that with his Tygers hart wrapt in a Players hyde, supposes he is as well able to bombast out a blanke verse as the best of you: and being an absolute Johannes fac totum, is in his owne conceit the onely Shake-scene in a countrey.

— Robert Greene, established dramatist, about upstart William Shakespeare, 1592

The common thinking about generalists (Johannes factotum, i.e. "John do-it-all" or Jack of all trades) is that they may able to do various things, but they're not very good at any of them. The reason for this seems self-evident: if you have time to learn the basics of many different fields, you don't have time to learn any of their finer nuances.

People use the expression "Jack of all trades, master of none" in a dismissive way, implying that not being specialized in anything is undesirable or embarrassing in some way. Yet generalists are chosen for many important roles in society. When one talks of a "family doctor", they usually mean a general practitioner with some level of understanding of most disciplines of medicine. Many CEOs, managers, and facilitators in business and tech tend to be generalists, too. Clearly society has special spots for these people which it claims are really good at nothing.

At the evolutionary level, "specialist species" are the first to go extinct when the environment has an abrupt shift. The "generalist species" are the adaptable ones, those that can pivot to different diets, different hunting and foraging strategies, and different climates when the need arises. Consider raccoons, cockroaches, and... humans. Whether we realize it or not, we owe our world-bullying success to being natural Jacks of all trades, not specialists.

That's the easy case in favor of those with eggs in many baskets. One basket crashes to the ground—no problem, because you have others. But individual humans aren't the same as species: Darwinian adaptation is a multi-generational affair based on innate traits, whereas people aren't randomly born with an excess of disparate skills.

In people, being a generalist seems to be, first and foremost, about a certain attitude or process, the variety of skills a secondary perk that comes with time. Generalists may appear to know "all trades", but they usually acquire that know-how just in time for it to be useful.

All this considered, the "master of none" bit sounds a little off. Something is missing. Why would society reward being mediocre at everything? Why aren't all generalists outcasts, at least for the first several years it takes them to build up a large toolbox of skills?

At this point in the discussion some people end up mentioning how fast-changing today's world is, and how flexibility and adaptability are more important than ever. Others recommend becoming "T-shaped" instead, i.e. generalists who have both breadth and depth by becoming experts in one field. I will discuss neither of those things, though, because I'm interested in something else.

I think "master of none" is wrong, not because it is used dismissively, but because it is false.

If generalists are given the key roles they do, it's because they're really good at some non-obvious skill that the specialists lack or avoid practicing. Generalists must be masters of something—something other than the typical specialization. My question is, what are they masters of?

Quick Learning

To return to my previous point, to be a generalist you must be, at the very least, a quick learner.

By "quick learner" I don't mean someone who memorizes a lot of information fast—a skill equally valued by specialists—but someone who can grok, in a short time, things that take place in very different contexts. That's not a complete answer yet, but a hint: generalists excel at something related to context-switching.

The first step we humans take to understand the world is to frame things—we mentally segment the continuous, seamless network of interactions around us into named black boxes like "car", "society", or "Jonathan". These mental black boxes, in turn, become the building blocks for the second step, the creation of the mental models we need to simulate the world and make predictions about what will happen.

Suppose you're trying to learn computer programming for the first time. You begin by learning what's what, build a new ontology. You're told that there are things like "variables", "functions", "expressions", "loops", and "branching". If you're a beginner, you don't need to know how each of these things works inside, the mechanisms that make them behave the way they do. They're just black boxes to you: they have a defined behavior and rules of application, and that's all you need to know. For example, a for loop is a black box concept, an object that simply repeats its contents a designated number of times.

This naming of the important moving parts, or ontology-building, is what I'm calling framing the task.

Then you move on to learn how those elements can work together to produce more complex results. If you take the for loop object and put an expression object inside it which adds the number 1 to the variable object called x, you'll get an ever-increasing number: the for loop repeats this x+1 operation over and over. This simple mechanism may not be useful on its own, but you can combine it with other mechanisms to make useful programs. You could add another expression inside the loop—say, multiply a variable y by itself—and stop the loop when x has reached the value N. In this way (you learn to predict) the program will compute $y^N$, the N-th power of y.

The process of learning to put those building blocks (e.g. for loops, expressions, variables) together in specific ways with outcomes you can predict (e.g. computing y to the Nth) is what I'm calling creating a mental model of computer programming.

If you've never done anything similar to computer programming before, this work of framing and model-building can be slow and difficult.

You'll need to forget some previous beliefs you had, like the fact that a loop is something that looks circular in shape. And you'll need to learn new ways of thinking, such as the fact that the computer will do exactly what you tell it to do, with no regard whatsoever for what you want it to do. Different context have different laws of interaction.

Here is where the generalists seem to excel. Being a "quick learner" must involve being nimbler at reframing and mental model-building tasks. This could be partly due to innate mental faculties, but I think it also has a lot to do with the approach and attitude towards the new areas of study.

The Mastery

No field of knowledge is completely unrelated to all others. There is always some overlap, either in the objects defined in two separate framings or in the ways multiple objects interact in those framings. This creates a pretty evident self-reinforcing effect wherein knowing more disparate fields makes it gradually easier to learn even more.

But there is more to it than simple accumulation. A good generalist is necessarily good at spotting patterns: even if a model is different—different labels, different ways to clump things together—it might be fully or partly equivalent to other models in different disciplines in subtle ways.

Many processes are context-independent, amenable to powerful analogies. The ability to recognize a familiar pattern in what looks, at first glance, like an alien world opens up shortcuts to understanding. And even when the pattern is similar but not identical to one previously known, spotting the bits that differ helps you cut to the chase and focus your learning.

Thus, if you're very good at cooking, with its complex recipes and accurate procedures, some parts of programming might feel more natural to you; and the art of balancing the organic and the methodical that you learn in a project management job might give you insights about how to maintain a thriving garden.

Another skill required of a true Jack of all trades is traveling light. Things like tradition and "common sense" are heavy mental baggage. Carry it with you for too long, and you'll even forget it's there to bog you down. To quickly learn a new skill or area of expertise, one needs to drop the baggage and be ready to start from scratch. Empty the Lego bucket on the floor and start playing with a brick at a time. Some call this "thinking from first principles", but it's only part of the story.

In any project and group of people, there are usually many separate goals that co-exist, sometimes in harmony and sometimes in competition with each other. As far as I can tell, generalists tend to be better at navigating those trade-offs. A specialist easily falls into a kind of "tunnel vision", becoming blind to all but a small set of standard goals, like corporate KPIs or completing a prescribed sequence of steps well. A generalist is never immune to the same pitfalls, but tends to be better at avoiding them. This is helped by the fact that, by definition, they come to each field with fresh eyes, but it's still a muscle they get exercise regularly.

A generalist also needs to be good at some form of systemic thinking—a kind of meta-framing—where the focus is on the structure of the problem and of the relationships at play, rather than predefined procedures and fixed categories.

A specialist can live within one framing their whole life: the ontology is relatively static, and the same kinds of things happen over and over. This allows them to focus on the fine-tuning of those processes, without worrying about cataclysmic changes. But a generalist needs to think about those same topics very differently. Every moving part might move any time, and no process is taken for granted.

Instead of focusing on how any given process could vary, a generalist needs to see how different processes arise from the system's interactions. It's a slower and coarser way to look at the same field, but it gives them a lot more agility when the basic assumptions change.

The last ability I notice in every generalist is that they get a kick out of reframing and remodeling reality. If you dread the sense of confusion and ineptitude that pervades the initial phases of learning, you won't get far as a generalist.

The young William Shakespeare, to whom Robert Greene (presumably) refers in the opening quote, was an actor, but he threw himself into playwriting with a passion that, it seems, irritated the incumbent specialists. He then branched out to poetry, theater management, real estate, and mentoring.

But this isn't just a matter of preference, a hobby or quirk that can be safely ignored by all others with different interests. Often you're forced to learn new things, even if you're a specialist. Welcoming the new, rather than resisting it, is going to make anyone's life easier.

The Something

To sum up, a generalist is someone who knows how to

• recycle existing framings,
• spot analogies and deviations from known patterns,
• think from first principles,
• apply a systemic meta-framing,
• balance trade-offs, and
• enjoy the learning process.

I'm not sure this list is complete, and not all generalists are amazing at all these things. But all of these skills can be trained, learned, and mastered with enough time. You can't become a generalist overnight. It's a gradual process that takes years of practice to excel at.

Even veteran generalists fall into generalist-specific pitfalls sometimes: dipping one's feet in too many fields at once, tumbling down rabbit holes, impostor syndrome, and so on. Avoiding these takes dedication, focus, and practice.

In other words, generalists are specialists, too. They are experts at... I'll call it "generalism".

The only difference generalism has from other specializations is that it isn't a neatly-defined field with sharp boundaries. Generalism is a meta-specialization, something more universal than anything you can call a "field". And for this reason, unlike most specialties, it's an expertise that you can recommend everyone learns.

Given how fundamental it is, it's surprising that, as far as I can tell, no school has a curriculum for anything like generalism yet. There are no generalism teachers in high school, nor a Generalism Department in university, nor job descriptions saying "must have at least 3 years in generalism".

Of course, some of these abilities are taught in school in one form or another—today's generalists learn them somewhere, after all. But this learning seems to happen almost by accident, a side effect of doing things like extra-curricular activities and group projects. Instead, school seems to be designed for the opposite effect: try many disconnected disciplines, then pick one and go as deep as you can in that. That's the only way, they claim, to be "job-ready".

The result, I think, is that those lucky enough to have a natural tendency for it, or to have the right teachers and environments, are the only ones who can hope to "specialize in generalism". I believe it doesn't have to be this way.

Not everyone needs to become a professional generalist, but everyone can benefit from learning a bit—or a lot—more of that skill set. For specialists in other sectors, this would allow them a flexibility and a perspective useful in tearing down those tunnel-vision walls and bridging the gaps between silos. And, very often, being "good enough" at a task, as opposed to being a specialist, is actually enough.

Unlike most other disciplines, I imagine no one would ever call the time spent being taught generalism a waste. ●