It used to be that airliners broke up in the sky because of small cracks in the window frames. So we fixed that. It used to be that aircraft crashed because of outward opening doors. So we fixed that. Aircraft used to fall out of the sky from urine corrosion, so we fixed that with encapsulated plastic lavatories. The list goes on and on. And we fixed them all.

So what are we left with?

As we find more rules to fix more things we are encountering tail events. We fixed all the main reasons aircraft crash a long time ago. Sometimes a long, long time ago. So, we are left with the less and less probable events.

We invented the checklist. That alone probably fixed 80% of fatalities in aircraft. We’ve been hammering away at the remaining 20% for 50 years or so by creating more and more rules.

We’ve reached the end of the useful life of that strategy and have hit severely diminishing returns. As illustration, we created rules to make sure people can’t get in to cockpits to kill the pilots and fly the plane in to buildings. That looked like a good rule. But, it’s created the downside that pilots can now lock out their colleagues and fly it in to a mountain instead.

From a great piece by Steve Coast on why the world is getting weirder. Follow the Pareto Principle long enough and you fix all the low-hanging fruit with a whole bunch of rules, leaving just the black swans unaccounted for.

Anyone who has worked on any tech product or service long enough, through many cycles, knows you can end up working on just edge cases. Often, when you hit this point, you're listening to a sliver of power users and are at the point of such diminishing returns that accommodating them might be counterproductive as a whole. All you do by adding that random feature they want is add some interface overhead and friction for majority of your users, whose problems you already solved.

At this point, if the user base is large and healthy enough, most smart and ambitious companies move on to launching new products and services with higher marginal returns on their resources ³. The resource vacuum is often exacerbated by the fact that the most ambitious employees would rather work on the new new thing. So they move on to the latest hot top secret project, leaving the former product or service in a maintenance mode, with minimal oversight.

Large and successful multi-product companies that reach this point often just kill off the product or service if the user base isn't large enough. Think Google Reader or Apple's Ping. A startup that reaches that point often pivots, sells themselves, or folds. ↩

It's usually the right near-term economic thing to do, but it can also leave some widely used products or services with chronic issues or imperfections that puzzle users and outsiders. How, they wonder, can a company with thousands of employees not bother to fix such longstanding and seemingly trivial issues? This is why competition is healthy, even if sometimes it seems like we have too many redundant products/services in tech.

Coast's post also includes some good career advice.

On a personal level we should probably work in areas where there are few rules.

To paraphrase Peter Thiel, new technology is probably so fertile and productive simply because there are so few rules. It’s essentially illegal for you to build anything physical these days from a toothbrush (FDA regulates that) to a skyscraper, but there’s zero restriction on creating a website. Hence, that’s where all the value is today.

If we can measure economic value as a function of transactional volume (the velocity of money for example), which appears reasonable, then fewer rules will mean more volume, which means better economics for everyone.