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My older relative is complaining that their working life roughly coincided with the time where computers became mainstream but were still hard to use, and now that computers have become easy to use (think smartphones and tablets) their (the relative’s) productive days are more or less over and all their hard-earned difficult computer knowledge is becoming obsolete. So they were the generation that had it hardest, because they had to deal with computers (unlike earlier generations) but had to do so before computers became easy to use (unlike later generations).