The Hidden Danger of Knowing What You’re Doing...

My parents built their own houses. They also designed and built a small hydroelectric dam, canned bears and constructed an arctic runway large enough (barely) to land C130s. My parents weren't engineers or contractors or food scientists. My mother's PhD was in the History of the Philosophy of Science and my father's was in Operations Research. Their lives and experiences were enriched by a simple belief: if you have a good enough liberal arts education, you can learn to do anything from a book.

In a way, my parents turned back time. When anthropologists study the development of human society they often to turn to specialization and hierarchy as key signs of civilizational maturity. With specialization, families stop having to do everything from hunting to basic tool building. Instead, each person can focus on one activity and exchange the benefits of their efforts with those who focus on other activities. Blacksmiths can excel at making tools, farmers at making food and so on. In our modern era, this concept of specialization has become ever more critical. There are degrees and certifications that cover almost every possible human activity - from bricklaying to computer programming to astrobiology. It is only by gathering together in a vast online community that we can assemble the enormous array of specialists necessary for modern culture and industry to flourish.

My parents moved in exactly the opposite direction. In order to survive, they had to become far more self-sufficient than is normal in modern times. They engaged in small-scale farming, they hunted and canned animals, they built homes, dammed streams, and harvested honey. My great uncle, who lived alongside them, worked with iron, copper, ivory, and wood to create artistic and practical masterpieces.

One of my great-uncle's creations - a samovar

My parents weren't truly self-sufficient. When they could get out of the river canyon they lived in, they purchased industrially-produced food, clothing and materials like piping. My father made the money necessary for these items trading mining company shares via ship-to-shore radio. Despite these concessions to the modern world, they engaged in a far broader range of activities than is normal today.

Their stories are great (and sometimes horrifying), but is there value in what they did? Given that human society advances through the process of specialization, were they achieving anything at all?

Oddly, the answer is in the question itself. The process of specialization, after all, is only a symptom of development. It is not its cause. The process of ever-greater specialization is often driven by people who step outside the constraints of pre-existing specialties.

Today machine-learning specialists are all the rage. They are only the rage because people who studied the intersection of neural processing, language learning and computer science — effectively non-specialists — managed to create a new specialty. The mass manufactured clothing my parents purchased only became a reality because of people who combined knowledge of materials (namely cotton and wool) with that of mechanics and pre-electric hydropower. They reached across specializations to see new possibilities.

In our modern age, we elevate one particular kind of generalist: entrepreneurs. Invariably, successful entrepreneurs see what didn't exist before and then make it a reality. Whether they are filling an existing market need or creating an entirely new market, they can step outside pre-defined boundaries.

Today, every effort is being made to make the act of creating new specialties into its own specialty. There are books that guide you through the process of market definition, funding, human resources management and exits. In fact, since the boom of venture capital in the late 1990s, the process of developing a company has become increasingly standardized and specialized. Being able to work within that standardized reality can yield significant benefits - most critically by enabling the startup company to focus on a much narrower problem set. Instead of every entrepreneur having to essentially reinvent how companies are built, there are increasingly standardized ways of doing most everything. As a result, the roles of Founders, Chief Marketing Officers, Chief Technology Officers, Heads of Product etc... have become increasingly specialized and standardized.

The entrepreneur relies on a multi-specialist’s skill in their moment of insight. Afterwards, though, they become company-building specialists. The best of them have started multiple companies — making a career of building new entities. The entrepreneur’s characteristics of risk tolerance, confidence, salesmanship, management talent and a desire for a big payday easily eclipse that of being able to see beyond our existing reality.

In fact, even their moment of insight often has to be firmly grounded in what people already know. For example, when raising money, it is always best to describe your company as combining pre-existing concepts (e.g. "this is the Netflix of Kitty Litter").

I wonder how Netflix described itself?

In 2018, the DuffleBlog (a military-focused satire site) published a piece titled: Army standardizes 'thinking outside the box' procedures. Today, I have numerous friends who specialize in just this: they help organizations and companies develop standardized procedures for encouraging innovation.

The world of hiring, driven by machine-based analysis, reinforces a reality in which the true generalist, with his or her highly unusual capability for systemic innovation, is largely unseen. There are no computer programs that find people who can see what doesn't yet exist.

Just try searching LinkedIn for somebody who can deliver unexpected value.

Despite all of this, we haven't yet reached the point where the true generalist has no part to play. A lack of awareness — reinforced by our desire to quantify and standardize everything — is not the same thing as a lack of need. To see the part the generalist still has to play, we just have to look past the entrepreneur. Instead of focusing on the attributes of risk tolerance, financial ambition or salesmanship, we need to focus on creativity itself. This process will lead us to discover the deployment of generalized skills in far more mundane places. A classic, but limited, example is in car manufacturing. Toyota started with an inefficient process and enabled their production-workers (very few of whom had degrees in industrial process engineering) to suggest small improvements to that process. Before long these specialists in screwing in bolts or painting metal had delivered one of the highest quality and most efficient systems in the world.

They worked beyond their specialty to deliver unpredictable value.

While their example is quite limited (they were coming up with better ways of doing jobs they were already doing), it is still illustrative.

Now, imagine filling a role in quality control, finance, computer programming or market analysis with a generalist who has a strong capability for learning. If you do this, and empower them as Toyota empowered its workers, something unexpected will happen. Your hire, who often won’t have the risk tolerance or financial ambition of an entrepreneur, will address a wide range of needs in inherently innovative ways that yield unexpected — and unpredictable — value.

The attempt to systemize innovation itself reminds me of the reactions to the mechanical clock as it spread across Europe. In many places, the clock was associated with the divine, giving order and structure to life. This reflects a determinist world view, where every human gear has its place.

However, reactions to the clock were not always positive. In a motif that would truly resonate in the age of industry, the Devil was seen enslaving humanity through the measurement of time.

This conception argues that humans should not be gears — even if we are able to make them so.

When I think about the future of society, I hope room will remain for the generalist. This is not simply to satisfy my own professional ambitions (I am an extreme generalist), it is also because I am sympathetic to that Scottish vision of the Devil.

Healthy human organizations, whether they are individual businesses or the manifestation of our global culture, are not simply made up of cogs. Instead, healthy human organizations are defined by constant, organic and unpredictable change. That change is often enabled by those who do not specialize.

In other words, by working with generalists, you will make room for realities you cannot yet imagine.

The results are almost guaranteed to surprise you.