> I'm always thinking about "Can I (or anyone) get back into this easily 6 months from now?"

People I work with get very annoyed with me because of this, but I am obsessive about documentation for this reason. Sure, it requires a lot of tedious writing and screenshots, etc., but it has saved me countless times. I still can easily get back into things years later thanks to documentation.

The caveat is that when people who are not as passionate as you maintain a product and seemingly forget about documentation.

In the old days, documentation was a very strict requirement on many of projects I was involved with. Now, in modern agile projects, it’s an afterthought at best, despite having amazing documentation tools that we’ve never had before.