I think it’s easy to exaggerate how often updates are regressions, because the ones that don’t turn out so well are going to sit in our memory more strongly than all the other ones that worked fine.
It’s like if you go to Starbucks every day, and in 20 visits your coffee was prepared correctly. Then on the 21st visit, something was messed up.
Which experience would be most memorable? The one where they messed up, not the 20 other experiences where everything was fine.
Most updates to most software
are made in good faith. Companies (at least, the ones not in a complete monopoly) don’t try to scam their customers, they want to keep you happy so you keep buying. They’re not trying to mess up your workflow.
And this is why resistance to change is such an unattractive trait to me: if you’re learning every day like you’re supposed to, having to re-learn something shouldn’t be such a big deal, and it’s not like most software updates are going to just completely change how everything works (especially when they’re frequent and incremental). I think boxed software is actually worse in this regard. I always hated having to shell out a bunch of money all at once for the next version and then go through a more jarring migration process, because each update contained years of changes all at once.
Arguably, Microsoft’s ribbon interface in Office would never had happened if Office 365 existed at the time. They needed a big visual change they could show off in screenshots to stimulate discrete sales.
Apple managed to do something as extreme as changing the underlying file system of my computer with a routine update, no clean install or data migration required. If I wasn’t a tech enthusiast, I would have had no idea it even happened! Can you imagine how mind-blowing it would have been if we could have had that experience in 1998? For most people in the 90s, upgrading your OS meant buying an entirely new computer because it was just that difficult.
I’d personally rather not sit around being bitter and cynical about things being different now, maximizing the bad and minimizing the good.