"Older versions are more stable"

The whole concept of LTS in development pisses me off.

Delayed upgrading, whether it's the language itself, dependencies or tooling, does just one thing: It makes future upgrading way more difficult, often to the point where the company eventually runs into this maintainability wall, and gets stuck in old, unsupported versions.

"But... stability!" — The tiny chance that the newer version has such serious stability regressions that it negatively impacts your own product doesn't weigh up against the clusterfuck you fall into if you push the task too far into the future.

You can relatively easily assess a new major language version using benchmarks and unit tests. Predicting the repercussions of staying on PHP 5.4 or Python 2.7 for another year, predicting the impact of upgrading the codebase later, that is almost impossible.

I'm not saying you should live on the bleeding edge in production, but as soon as a new stable version of a core technology is released, just fucking drop everything you're doing and port those deprecated methods!

I created some test entities specifically for our staging site. Written in all capitalized letters in the BIG TITLE of the entity I included DO NOT DELETE. This is very clearly visible in the CMS. What's the first thing the content managers do?

You guessed it.

I guess if plain English doesn't work, I'll have to use Kindergarten rules and put a custom lock on them so they can never be deleted.

Muad'Dib fullstackchris can already predict the future, in a few weeks: "hey!!!! fullstackchris, I can't delete these test entities!!!!! whats wrong with the system?!?!"

sigh...

First, realize that trying to accurately estimate how much time something is going to take is akin to accurately predicting the future and that people who ask you to do it are stupid. Then realize that sales-oriented deadlines are the source of all that is evil. Then shift away from sales oriented software. Instead focus on selling existing features and new features on the roadmap have no deadlines, they're done when they're done. Then realize almost no workplace will let you truly do that because chasing the sale is all that matters despite the latest buzz word rhetoric. Then estimate enough buffer to give you a reasonable time to complete it without calling your abilities into question. Then finish it faster so you score points with management, but not every time because then they'll begin to expect it. Now you have leveled up in mind games, an unfortunate but necessary tool in the tool belt. Then hate on sales oriented software some more, rinse and repeat.

Predicting the future can be tough