I agree with this in general but it can be tough for financial/business/order workflows where an irreversible change may be initiated. From the software perspective an audit log or Git-like history would easily mitigate these concerns but they usually don't exist. And "non-technical" users often just want to "know what buttons to click" to do their job.
To the point of the main article don't think I ever had the opportunity of using Windows 2000. Remember jumping from 98 to XP? Not sure about ME/Millennium either and if it's the same or a variant of 2000.
Yeah, and this is definitely a big reason why people are afraid to click and explore.
I still don't understand why big enterprise software still lacks any kind of version control. AUdit logs, yeah, but most big ERPs and other similar products don't have an easy "roll back this change" feature.
I think users knowing that they could immediately undo whatever they did and get back to a safe and known state would do a lot to encourage exploration and learning.
I don't know if there's ever going to be a suitable environment to have this conversation, but many people in any society are just not smart enough to experiment with things especially if those things are non-physical or abstract.