The Cliffs Of Insanity

I seem to be in the metaphor business lately. 

First there were rabbit holes. Now we have cliffs. Big, steep ones with ominous and foreboding names.

Anyone of a certain age remembers where they were (and very likely who they were with) when they first saw The Princess Bride. In my humble opinion, everyone regardless of age should see this movie. It’s wonderfully well written, delightfully performed, downright witty and an incredibly good way to spend an evening. But I speak today not of the whole movie, but of one fundamental part of it.

The Cliffs of Insanity show up relatively early in the movie. They were the first major hurdle in a long odyssey of obstacles and innuendo. Theoretically insurmountable, they were nonetheless scaled by the character played by André the Giant (while carrying three others, just for good measure) and quickly followed by the mysterious masked man. It is a scene that gifts us with one (of many) of the more memorable lines of the movie. Despite cutting the rope from the top of the cliffs, when the man in black is inconsiderate enough not to die, Vizzini exclaims “He didn’t fall? Inconceivable!” To which Inigo Montoya replies “You keep using that word. I do not think it means what you think it means.”

Obstacles and thinking are at the forefront of my existence right now. I’ve had some deep and intense technical work that I’ve needed to focus on this week. While I can be technical (please don’t tell anyone, though; it’s an extremely well kept secret) I have my limits. I have to do work on several of my web sites that are increasing the geek factor to exponential levels beyond where I normally function. This is taking a lot of effort and concentration, and resulting in no small amount of consternation to boot.

This is pretty much the point where this particular metaphor kicked in. While the cliffs of insanity may not have been as insurmountable as claimed in the movie, no one said scaling them was easy. And so it has been for me.

When we are faced with obstacles, there can be a very strong temptation to look away. To find the easy way. To take a shortcut. The cliffs don’t offer one; you have to go hours out of your way, or you have to confront and scale them head on. Those are your options. In the lead up to this challenge, I’ve been trying to do the next best thing and pretend they are not there. It’s a hard thing to ignore looming cliffs, but I’ve certainly given it my best shot.

That the cliffs are a metaphor is obvious. It is helpful and important to explore just what the cliffs are being used to represent, though. For me, here and now, it’s the process of learning.

We learn on different scales, at different paces and in different ways. Growing up, we progressively accumulate an understanding of the way of the world and our place in it. Learning feels natural, because it’s the only way forward. At the outset, everything is a challenge and each circumstance is a learning opportunity. We are progressively learning through most of our teen years, until we miraculously reach a point where two things happen: we stop learning, and we hold the opinion that we know everything there is to know about just about everything. Such is the confidence of hitting your twenties.

Push through that period of overconfidence, encounter a few setbacks along the way, and you might come to appreciate that there are still areas in which you are not expert, and learning opportunities that are still available to you. We don’t approach those opportunities in the same way, however. Now there is choice involved. Learning isn’t the default going-in position; we can choose to learn, or we can choose to avoid.

The reason that we wrestle with this choice is a profound one. We have ego in play. We struggle with our idealized view of our potential selves. We are confronted with the fact that learning means that we are not expert, and that there are areas where we are not competent. The further away from expert that we find ourselves, the more insurmountable the hurdle before us appears, until the cliff soars above us, imposing and daunting. 

Where my current challenge lies is in a realm of technology which up until now I have had only passing familiarity. That familiarity has been sufficient. I knew what I knew, and while I was the first to admit that I wasn’t expert, I at least had adequate skill and ability to function. I knew what I needed to, I could get the essentials done, and I tended to leave everything else to the experts who have far more geek cred than I do.

The challenge is that, in the time that I have been navigating my way around web sites and server technology, the state of the art has advanced considerably. There was a time that you needed a passing familiarity with HTML and some reasonable graphic design abilities and you were good to go (and if you really liked the work, you could make a tidy fortune as one of the early web developers). Java and Javascript aren’t necessarily new, but they’ve been joined by PHP, Ruby, CSS, SEO, CMS, Apache, responsive design, user experience and a host of other acronyms and concepts.

Building a competent web site has always involved measured contributions of technology, design, programming, marketing, empathy and magic. Each of those areas have progressively ratcheted their capabilities ever upwards. It is progressively harder to be a master of all of them, and significant work to attain mastery in any one discipline. To be a journeyman dilettante is to court disaster. Enter me.

In an effort to keep pace with where the technology finds itself today, I’ve had to confront my lack of knowledge on several fronts. I can navigate around the front end of a web site just fine. Graphic design, image manipulation, copy editing and overall structure is something I don’t particularly find intimidating. Over the last few years, I have been confidently doing what I know how to do, while accumulating a significant technical debt on multiple fronts. Search engines don’t work they way they used to. Web design is more complex, and also now looks a whole lot like programming. Usability and site optimization is frequently presented as a black art of structuring content in ways that both site visitors and search engines think. Designing for desktop browsers first and mobile as an afterthought has been turned on its head. 

The consequence is that things I thought I was relatively proficient in I no longer have mastery of. I arguably barely qualify as journeyman. The technology has advanced on several fronts enough that I’m in many instances starting over. This reality is both overwhelming and frustrating. It is no less a product of ego, mind you. In this instance, the consequence is that I’ve theoretically not avoided learning. I’ve just avoided realizing that the current state of learning has passed me by, and if I still want to play in this game I am going to need to catch up quickly.

I have long had a strong sense of how I best learn. What does not work for me is rote memorization. Telling me exactly what to do and how to do it is the surest shortcut to rebellion. I will find a different way to do it just effectively. Part of the reason of that is sheer obstinancy, I suspect. The other part is that in finding a different way I am working my way back to first principles, and forward from there into a new and still serviceable way of getting it done.

What is fundamental here is, well, what’s fundamental. I need to understand. I need to know why. Once I’ve got the conceptual understanding, then I can work out the details of how to actually function. Without that understanding, though, I am flailing. I’m dangling on a rope over the cliff, with a sneaking suspicion that someone at the top is trying to cut me loose.

The interesting thing we are all wrestling with now is the interconnectedness of things. This is where I think the challenge for many of us lies. It is one thing to be grappling with understanding, competence and confidence on one front. It is an altogether different thing to be working out several things on several fronts at the same time. It was this reality for me that took me over the edge just yesterday. Once challenge led to another. Fixing the second challenge in turn revealed several more. Resolution of each of them required skills that I don’t currently possess, in several different domains. That is an easy short circuit to overwhelm.

This feeling isn’t new. It also likely isn’t going away. The trick is knowing what to do when we experience it. It means needing to have a strategy to work through and keep on climbing.

Where this starts is a willingness to recognize that you are venturing (or have already ventured) past your comfort zone. What will make you successful going forward is not going to be what got you here. Different strategies are going to be needed, built upon new and different levels of understanding.

That means being willing to go back to basics, and letting go of—or at least augmenting—what you currently know. This is possibly the hardest part of learning: accepting that a preferred and privileged view of the world no longer works, and we’re going to need to rebuild and reframe how we think and act. Getting stuck in “this has always worked for me in the past” (a personal variation of “this is how we’ve always done things around here”) is a level of denial that will not serve us.

From there, you need to find reliable sources you can draw on in reorienting your understanding. Going back to my current personal journey, that has been an interesting exercise all on its own. On the topics that I am exploring, there is no shortage of opinion and there are multitudes of self-described experts offering a modicum of insight to entice me to pony up and buy their product, their training or their services. It would be one thing if you could triangulate across multiple perspectives to figure out what is true, but many of those perspectives actually conflict. This has required a refined level of discriminating expertise and insight, and identifying those who are genuinely trying to help and educate from those who are simply trying to sell something.

What makes this very complex is when you find yourself open to multiple avenues of learning at the same time. Very often, these are in some way connected and supportive of each other, but approaching this from the outside in a learning mode, it can be difficult to ascertain just how one domain influences another. Bottom line, you need to start somewhere. Hopefully, this choice is somewhat informed and educated. Regardless, you need to make a call, with the willingness to retrace your steps as necessary.

Last night, I found myself pretty close to overwhelm. I had three different domains of exploration to tackle, all of which in some way related to each other, and no clear sense of where to begin. Chaotically moving from one to the next might feel like action (in the same way as playing whack-a-mole at least expends energy) but isn’t necessarily a productive path forward. In this, I once again found stepping away to be the most valuable thing to do. I went to sleep, let my subconscious noodle away on the problem, and woke up in the morning with clear set of actions and a rough strategy and sequence  for handling them.

Learning is not inconceivable. Nor is progress impossible. The cliffs are not insurmountable. You need to put one foot in front of the other, lay one hand over the next, and keep on climbing. That requires willpower, it requires a level of adaptability and it requires the humility to recognize that what you thought you knew is insufficient in comparison to what you need to know now. Keep learning, keep growing, keep striving, and there is no end to what you can accomplish.