This is a legitimate way to analyze things, and you're effectively analyzing the relative entropy of outcomes.

This is why for instance, strings will naturally tangle when exposed to random movement. There is a only a single configuration that is untangled and infinite tangled configurations, so given enough random energy will always tend towards a tangled outcome.

You just discovered entropy!

This is why I hate linear planning. Pick an end goal and devise a process for approaching said goal. Correct the process as needed along the way.

Doesn't fit in a gant chart, though, so my boss never listens.

Well, that's just plain statistics of entropy: if there are two possible outcomes, there is a 95% chance of it being the wrong outcome. :D

Throw in some Sturgeon's Law (90% of everything is shit), and we are all running to stand still.

Entropy, like dropping a box of spoons. But in your life you can just shift your view of what's right and wrong. People act like there's one right path - go to school, get a job, get married, have kids,... There are a billion right paths and you can choose any of them. And if you choose not to decide...

Anna Karenina principle

"for success to occur in a complex endeavor, all key factors must be present and work correctly. The endeavor does not succeed when even one essential element is missing, meaning there are many different ways to fail"

"Society is doomed for one very simple reason: it takes dozens of men working months with millions of dollars in material to build a building, but only one dumb-ass with a bomb to bring it down." – Jason Pargin, John Dies at the End

Tangled Cord Theory

I’m stuck in the definition of what is right and wrong?

Almost every mistake in history can be traced back to somebody abandoning reality in favor of their own.

The more general statement is it's harder to build something than it is to destroy it. There are limited paths that will reach a given goal, but nearly unlimited paths to undo that accomplishment.

Things don't actually go wrong they just don't go right.

A corollary to this thought is the so-called [persistent] "attacker's advantage": attackers need to do stuff just right only once to be successful, while the defender must do always, everything right to be successful at defending.

That depends upon how narrow your definition of "right" is. Sort of reminds me of this parable.

This is called Entropy

The specific type of entropy you’re describing is called “Social Entropy” but in all cases entropy is simply the fact that there are (usually) more disordered states for a system to be in than ordered ones. So if a system can undergo any sort of change, it is just generally more likely to become less-ordered than more-ordered.