This was my experience even in the Windows NT/upcomming 95 days. Even my dad fought my love for computers every step of the way because all he ever saw them do was play games and sit on the desk of receptionists.
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If you aren't aware of how slowly some people pick up on the changing world around them, I can tell you that I've experienced some award winning ignorance. A work-acquaintance, probably approaching 50 at the time, saw me using a MacBook. He said "Apples? I haven't seen on of those in a long time. What's so special about them?" I went on to describe how easy the UI is and how the machines are always so thin and minimal with top-shelf quality batteries and displays. His eyes glazed over before responding, "Oh hey, don't they have that problem where they can only do one thing at a time?" I almost couldn't believe what he was saying so I clarified, "You mean no multi-tasking like in the 80's?" "Yeah". This was around 2008...
I get it. I worked with one ad rep from 2004 to 2018 and she was willfully ignorant of technology. Her primary mantra and one which she issued proudly was "I do not DO computers!" When I first started working with her she had to be in her early 60s.
It was extremely frustrating because she was also a pathological liar and narcissist. The only person she cared about was herself. So for the first few years, I actually had to handle her email. This was eventually reduced to three times a day and eventually my weak-kneed coward of a boss shoved a computer in her office over a weekend.
Oh, the knockdown-drag out fight that ensued between them over that!
About this time you're wondering why she was never fired, especially for treating the boss like her vassal. Essentially that was because she brought in the majority of the profit for the business, but there were some other things that over time we employees reasonably made assumptions on.
She did manage to change, but only because it was forced on her. Now, you're probably thinking this supports your last paragraph and in a way it does. But part of my job was also as IT for the company. In her case, this meant her making the same mistakes and my fixing those mistakes over and over and OVER again for 14 years. She may have been forced to use technology but no one could force her to remember how to use it. I could explain something to her, and then in five minutes I'd have to explain the same thing again.
She absolutely refused to retain anything that was taught or shown to her. It wasn't because she was dumb, it was simply because she didn't want to learn it - any of it.
And why not? All of us working for the company were there to serve her and her alone. We were all her servants and would all do what we were told. At least this is the conclusion everyone eventually reached about her. It never changed because my boss was too much of a coward to fire her.
I know there are others like her out there - she can't be the only one.