Jack of All Trades, Master of None

...is often better than a master of one

Originally posted on Medium in 2017 and, personally, I think one of my better writings ever.

I’ve been having this conversation a lot all across the spectrum of people in careers / art / schooling / etc. so I wanted to lay it out more centrally and try to describe is a broadly as possible for everyone.

The above chart is how I feel whenever anyone uses any of these terms.

One caveat is that this chart is more like a two-axis spectrum — while there’s quadrants, you can have people closer and further from the lines as they get better / worse in each axis and so on, nothing here is inherently binary.

Mostly it comes back to a) kids who are in school now and looking forward to their careers and b) peers of mine who are in the process of hiring people and seem to also misunderstand these quadrants when they’re talking about people they’ve interviewed.

‘Jack of all trades’ is a terribly broad category, in truth, and it’s used to describe anyone who isn’t a deep specialist in a field, but doesn’t describe how good they are at multiple things.

The problem is, we can’t necessarily condense this into one value unit. We have to be a little bit smarter and more contextual than that.

Kids are trying to grow up to become as valuable as possible and prioritize their future learnings / activities to optimize that. Bosses are trying to hire the most valuable employees and get the most utility out of any given hire. Makes sense from both sides, so we can talk to them both at the same time when we describe any given person’s value (which is reductive, but here we are).

General rules of thumb as I see them:

• a generalist is more valuable than a specialist in a world of increasing change and demanding resiliency / flexibility; specializations go out of style / usage really quickly. A top tier Flash artist a decade ago is almost certainly doing something else today because they’ve adapted or died.

• Ideally you’d be a top tier person in multiple useful mediums (multi-expert) instead of jumping from one dead specialization to a new specialization because…

• You are the most powerful when you can combine things together. The sum of your skills is greater than the parts. If you can code AND design, you’re more valuable than both a coder + a designer would be. This multiplies even further if you can, say, code AND design AND write.

• Ideally you would learn mediums that never get replaced. Writing has been around as a communication tool forever. They can’t make, you know, Writing 2.0 and suddenly kill your skill set. Telling stories and engaging people is itself a skill that you will likely adapt to mediums (say, prose into social media) but never fully need to re-tool from scratch. This is good.

• Multi-experts are generally strong because they can be top tier in 1–3 things and mediocre in a dozen more, and that sum-of-parts multiplier will still work in their benefit. The trick is weeding these people out from the generalists who are just genuinely mediocre in a dozen things.

• Being a generalist will help you learn core skills faster. It’s that Steve Jobs dot collection analogy. For me personally, 3D rendering skills taught me to draw better, photography taught me framing and lighting, making videos taught me pacing and story, writing taught me introspection — for Jobs he cites taking that typography class as a source for Macs having fonts. We never know where these things will line up, so trying and doing as much as possible comes back to that multiplier of output ability; value.

• Anything specialized will be replaced by robots. This one is a future-facing idea, but with the exception of research and exploratory human-y type specializations I would be worried that any activity too specific can be taught to machines and codified into procedures. Multiplying mediums creates serendipity and permutations of options for you and your craft.

• Finally, and this one is maybe a personality thing: learning a lot about a lot is just more fun. I get bored easily, so jumping between mediums and finding ways to be valuable by combining things that people have never seen / never would have connected before is super fulfilling for me.

Some cons to / for generalists:

• Proving your value requires effort. Being a boss who can’t easily reduce your skill to one axis is effort. In the old days of assembly-line style businesses, you either did your specific activity well, or not. But it gets infinitely ambiguous when your activity isn’t one quantifiable thing. Unfortunately, getting hired by these old bosses is an uphill battle of showing them how combining different mediums (maybe some they had never even heard or thought of) can be beneficial to their business. But! This is also where you can provide the most value. If they aren’t utilizing these combinations and you can multiply their output, it’s a huge win.

• Knowing what to do is hard and often basically random. You can never tell what is or isn’t a good dot to collect until after you’ve seen it be useful / useless (and sometimes you won’t use certain dots for years after you’ve collected them — sometimes the solution to a modern problem is a weird magazine you read in the 90’s and triggered some idea in you)

• Proving that you’re a multi-expert is nearly impossible in a world where most people don’t believe that exists. The idea that someone can be top tier in multiple categories is incompatible with a world generally mediocre in every category. It’s funny sometimes that tech talks about unicorns as being this magical person who can do two things when multi-experts exist who roll in a half dozen mediums with industry leading skills. Most people believe in the generalist-specialist binary. You’re either good at one thing, or half good at multiple things. You’re never allowed to be fully good at multiple things.

But, they exist. You can exist.

A final parting thought: you can also ignore all of this when branding yourself. No one really likes to read “polymath” in a resume. I roll my eyes when I come across them too, let’s be honest.

When it comes down to it, the modern scheme of being a good worker is having the reputation for getting stuff done well. No one cares how you did it, no one other than your ego is interested in being a multi-expert or how you suddenly connected obscure things into a cool one. They just see the finished product — was that advertisement cool? Did it sell well? What’s the ROI? Good. Quantifiable numbers. Let’s hire him again.

In the end, this is an internal measure more than anything. Providing value is the output, being a valuable person comes back to that chart, but that chart isn’t in itself a measure of value. Execution is. Combinations are. Multiplication of skillsets is.

Make good work, however you do it.

Go. Fight. Win.