The Crow and the Cave Dweller

The Short, Brutish Life of a Web Professional

In 1996, I landed my first paid web project. And even though I was midway through a post-grad program I’d worked very hard to get into, I knew that web, not the other thing, was what I wanted to do. Learning and consulting, designing and developing, repeating. All of it. That’s what I wanted to do.

Knowing what I wanted to do and being able to make a career out of it, though, were two separate things. It didn’t take long to learn there’s a surprising amount of business that goes along with turning a passion into a profession. Some of it clicked into place and felt at home, some of it didn’t. At least not at the same pace as my feel for the craft itself.

It would be eight years before I’d find any real balance between the two.


In Architecture (the career I spurned), there’s a widely discussed concept of designing Ducks or Decorated Sheds. A Duck – which is a reference to an actual building shaped like a duck that sold, you guessed it, ducks – is a building designed in a way that informs its purpose innately. A Decorated Shed, on the other hand, requires signage to inform its purpose.

Coming up through an Architecture program, all you want to do is design Ducks. You want to do it in new and clever ways, though. You don’t want to be too overt or obvious. You can’t just design a library that looks like a stack of books. You need to use Jedi mindtrick level persuasions. “You are looking at a duck.” “I am looking at a duck.”

The reality, however, is that the closer you get to the logistical aspects of your creation, the less chance your decisions come up Duck. At some point, it hits you: you’re probably looking at a lifetime of designing Decorated Sheds. Maybe you’ll french in the occasional Easter egg to make you feel like you still have it, but the magic will be gone. You’re going to make Sheds. For a living.

This is a long way of opening your mind to the idea that stranger analogies than the one I’m about to make exist.


The Crow and the Cave Dweller

In the creative services industry you operate in one of two ways. You eat what you can kill, often working linearly and focusing on one aspect of the cycle at a time, or you raise a village, creating systems and workflows that allow multiple disciplines to operate in tandem. In the first method, you gain efficiency through focus. In the second, you gain efficiency through process.

Most freelancers live in the first camp. Focus on the sale, then on production. Repeat. Agencies almost always operate in a village model. Standardized processes. Specialization of labor.

Web largely follows these traditional models, either because we’ve modeled bits of our own businesses after the old-guard or simply because we’ve made many of the same guesses and gambles.

Web has its own permutations, though. I know web freelancers who operate more like a village and web agencies who eat what they kill. These are the wonderful misfits who’ve studied or stumbled their way into something better. Freelancers who’ve picked up processes from agencies. Agencies who’ve learned to hustle or pivot watching freelancers.

The distinction between the two is less about their size and specialization of labor and more about the way they think.

Which brings me to my new classifications, my ode to the Duck and the Decorated Shed. The Crow and the Cave Dweller.

I won’t claim a favorite – both subjects are destined to live short, brutish lives – but I’ll tell you after nearly two decades of being in business, one will be far less stressful in the long-run. I’ll let you guess which one.

The Cave Dweller

Cave Dwellers fall into the Eat What You Can Kill camp. You will know them by their wild revenue swings and general distaste for the business aspects of the profession. You’ll also spot intense focus and skill and would probably find many of the most recognized and well-regarded individuals in our field among its ranks.

Why Cave Dweller? It seems so negative. I’ve been making this analogy since I set out. The cave is the craft. We leave it to hunt for new business. The bigger the hunt, the more time we spend outside the cave, out of our element, away from our craft.

I’ve never actually thought of cavemen / Neanderthals as being unintelligent, though. I’ve always thought of them as badasses. Stubborn badasses, maybe, but I’ve never met a real one. This is just a tribute.

People who operate primarily inside their cave learn to hustle. Or they starve.

I gravitate toward the cave life. There are no phones in my cave. But it’s hard to stay there forever.

The Crow

It takes a crow only a small part of the day to gather what it needs to survive. The crow’s resourcefulness and adaptability allow it to do more than simply survive.

Did you know crows are one of the few non-human animals to play? Well, they are. I don’t know which came first, but for the sake of this writing, we’re going to assume the Crow plays because it has time to. Why does it have time? Stay with me.

Crows are able to make tools and solve complex problems and puzzles. Here’s a crow making a hook to get a tiny bucket of food. Here’s a crow solving an 8-stage puzzle in about a minute. Here’s a crow eating walnuts. Here’s a crow fishing with breadcrumbs. The stories and videos go on. You get it, though. Most birds would just eat those breadcrumbs and spend the rest of the day looking for more.

It’s pretty clear how this applies to professional web humans. Some of us spend the day searching for crumbs.

At the individual level, thinking like a crow might mean setting up a system for recurring revenue. Becoming a hosting reseller. Creating a product. Getting listed as a development partner of a popular platform. WordPress VIP. Magento. Shopify. Whatever.

Similar patterns apply at the agency level, but now we include business systems. Maybe it’s creating organizational structures to allow greater specialization of work. A project manager, a designer, a front-end dev, a back-end programmer. Repeat.

Did you know too that crows can actually tell humans apart? They recognize facial features. They remember behavior. This human is okay. That human is bad.

I couldn’t even make up a better analogy for how you need to pattern your client profiling. “You’re going to get a huge amount of visibility working with us. Take that into account when you put together your proposal.” The crow wouldn’t fall for that. The crow would move on.

As fascinated as I am with crows, though, it’s hard to call them a sexy bird. They’re certainly no Peregrine Falcon. And just as the young Architect from our story only wants to design Ducks, I’d prefer greatly to stay in my cave, focusing on my craft. Venturing out and thinking like a Crow sometimes feels like selling out.

I have a complicated relationship with business. I feel like it’s healthy to go back and forth between the Crow and the Cave Dweller. After 19 years in the industry, though, I’ve found that if you don’t upstream your business systems, you’re in for a horribly stressful life. Having time to play is incredibly important, and having a family multiplies that need.

Somewhere earlier in the script I mentioned I wasn’t going to claim a favorite. It depends on so many things. If you’re a starving artist / struggling freelancer wondering why everything is so damn hard, go find some Crows. Pay attention to them. If you’ve fallen out of touch with your work, go find your Cave.

Sometimes it’s that simple.