The Creative Case for Cross-Training—or Why Jack-of-All-Trades Has It Better

Whether we admit it or not, we love human extremes.

Think about common heroes. Many of them are known for being the BEST at something.

Muhammad Ali is known primarily for being the Best Boxer (potentially also best shit-talker).

William Shakespeare is (in English, anyway) something like Original Best Writer, Father of Puns and Innuendo.

Paul Bunyan is Best Lumberjack slash Tamer of Blue Oxen.

You get it. All of them are beast-mode at something in particular, and THAT is what everyone knows. The rest is trivia for cocktail parties.

But what happens to people who are—you know—pretty good at, like, a bunch of things? Do they ever win stuff? Do they ever get famous?

The term for this kind of person is “jack of all trades,” and you’ll often hear the reminder: jack of all trades, master of none.

But most people have forgotten the end of the original proverb. Jack of all trades, master of none—but better than master of one.

Robert Heinlein put it more bluntly and more concretely: "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.

At Code&Quill, we prefer to be Jack if we have to choose. Because that way, we’re flexible and ready for more of whatever's coming. Because creativity is (in many ways) about drawing unexpected connections—and a wider pool of experience means more room for connections. (And yes, because specialization is for insects.)

Here’s a case in five arguments: why creative, cross-trained, Jack-of-All-Trades people have it better, in life if not also in work.


1. In direct competition, there will always be someone better than you.

For our immediate purpose, an "expert" is someone who chooses primarily to specialize, to deepen an already-deep skill or talent.

Let's be clear: the world NEEDS experts. We're not about to bitch about smarty-pants people when some of them are curing cancer. Plus, there's the tried-and-sometimes-still-true "go to college and get a real job" case for expertise, since experts are likelier to have real-world perks like: 

  • Job security
  • Health benefits
  • Fewer questions at family dinners

But experts—be they scientists, competitive runners, or rock stars—are also putting a LOT of eggs in their one basket. And if what's most important to them is becoming The Best (as is more common for athletes), their margin for success is razor-thin. (Not to mention: think of how much opportunity some people sacrifice to do that one thing.)

Even if you are the bona-fide Best at something in your lifetime, that sacred standing may not last long. What makes a legacy is everything around that monolithic talent, and that's where some of the brightest stars of history have truly succeeded.


2. People who combine talents are automatically more interesting.

Now think about the (Dos Equis) Most Interesting Man in the World. A recent example:



Aside from his pleasing masculine voice and unbelievable good looks, consider this possibility: he is The Most Interesting Man in the World because of his insane range of talents. (It's fun to notice that he's doing completely-separate, unnarrated feats in the ads, like stealing foxes and airlifting grand pianos into the desert.)

But seriously. In real life, some of the most interesting people (past and present) are polymaths, people who were known for a variety of different accomplishments.

Common examples from history include Leonardo da Vinci, Ben Franklin, and Thomas Jefferson. (The links are Wiki pages... just skim each article intro and you'll see what we mean.)

Contemporary examples include James Cameron, Richard Branson, and—of course—Elon Musk. (Again, just skim the start of the linked Wikipedia pages to feel instantly inferior.)


3. Learning many things makes you better at learning.

Stephen Hawking once claimed that "intelligence is the ability to adapt to change."

For adaptation, a larger body of knowledge (i.e. information) is certainly useful for adapting to a larger variety of situations. But equally useful, if not more so, is the flexibility to learn new things quickly—and with minimal pain or personal damage in the course of failure.

Over time, educated people begin to understand the "meta" of learning: that there are certain patterns and rules which govern (or at least describe) all teaching and learning, all forms of skill mastery, all types of subject-matter understanding. We do, in fact, "learn how to learn" at a deeper level.

People being educated process information; educated people process how information works and thus give deeper analysis to each piece of the information with which they're provided.

Sure, expertise is exclusive; if you understand ONE thing better than anyone else on the planet, you might be Grandmaster of that subject. But unless you're a master (or at least proficient) in multiple subjects, you won't be able to explain possible solutions to complex interdisciplinary problems—or even properly describe the problems themselves.


4. You don't know (what you don't know) until you have experience.

Here's a simple (and slightly embarrassing) example of what we mean.

Kevin, our Customer Service Chief, likes Mexican food. So far as he remembers, he always has. But for the longest time, he avoided guacamole. One fateful day in college, when he finally tried it, the taste of guacamole about blew his brain out of his skull.

Maybe you're wondering: what was Kevin's silly reason for avoiding guacamole?

Because guacamole looks (sort of) like spinach soufflé, which Kevin has hated all 40 of the times he's tried it from a young age. But only experience could teach him the real, emotional difference between guac and the SS. (One is avocado ambrosia while the other is green demon vomit.)

As oddly-specific as that example might be, it explains a LOT. You don't truly know things (including your own emotional reactions) until you have seen, heard, felt, tasted, or smelled the difference. And then, once you have experienced something, you can speak with authority on that difference because you remember it in a way that's bigger than logic.

Even limited experience—like one bite of a new food—is a kind of pure and unadulterated knowledge. In a small way, even that tiny experience changes you (since you can't untaste or un-experience something).

Best of all, that kind of experiential knowledge can be yours for incredibly cheap: just the time and risk required to take a single bite. 


5. Mastery is expensive, familiarity is cheap. Both get stuff done.

Imagine you could be expert in everything. You have an entire encyclopedia's knowledge in your head, and you're proficient or better at every skill imaginable.

Theoretically, you could do nearly anything yourself—even complex, intricate tasks like (A) performing surgery or (B) building a two-story house.

But there's still one problem: you're still just one person who, for all your brilliance, does not have superpowers. You could do any one thing (at a time) well—but you can't do everything well all the time.

In the case of performing surgery: You can't perform (most kinds) of surgery on yourself. (Sure, you could remove your own appendix like this guy had to, but good luck doing brain or bypass surgery on your own.)

In the case of building a house: Plenty of people have built their own houses. In fact, there's a guy who's (almost) finished a whole cathedral by himself. But it's probably gonna take a LONG time—and especially if you're doing literally everything yourself, you probably can't do much else with your life while you're building that house.

For projects of any size and seriousness, there's just no replacing extra hands. Even if some people are "less trained" than others (nurses assisting doctors, foremen directing carpenters, etc.), some things are only possible when people work together.

This is why, in virtually any leadership role, cross-training and communication skills are so important: you have to understand people's jobs AND have the ability to communicate with those people in ways that help them do those jobs, even if they're not specialists in the same things.

Even if you're no longer Expert in Everything—and you're back to being a regular "jack of all trades"—familiarity with a subject means that you can get good help from an expert. And in the reality we inhabit, where you were never Expert in Everything and you'll inevitably need others' help, communication as a skill has power that even omniscience doesn't.


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  • Robert

    This was a fantastic article that just made me feel great about myself. Friends call me a Jack of all trades. Though a part of me has been interested at being the best at something…I never have been able to keep my passion for any one thing. See, touch, taste many things…and DO even more!! I have C&Q notebooks to help me organize and jot down good and even great ideas. I do recommend people to try out their notebooks!! I, for one, am satisfied!

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