I dunno about even that. Forgive my example (though I love bringing it up, since so few people seemed to have grokked it in the time since initial release): in the video game Bioshock: Infinite, one of the later levels sees you transported into the far future of 1984. The game's setting, a flying city named Columbia, which was characterized by its almost cartoonish levels of capital-A capital-P American Patriotism, had featured in its original Gilded Age incarnation many of the ills of turn-of-the-century American society, including racism, an exploited working class, religion-driven insularity, and a predilection for violence. However, it had also presented an enthusiasm for the new and curious, an ambition for high living standards, and other cultural accoutrements that are usually associated with forward-thinking societies.
By this late-game level, however, the city has descended into dystopia. Why? Well, a three-quarter century game of telephone. The ideals of the city's original founder, already imperfect, were further transmitted imperfectly to his successor and her charges, whose personal traumas further warped their interpretation of Columbia's intended values, and the actions taken in their name. That repentant successor, having lost control of the city's populace to a revolutionary fever, sends you back to the past just as Columbia's weapons begin to level New York City (a caricature of America destroying its real-life historical "center").
It's a metaphor, of course.
It's easy for the soul of an idea to get lost in translation. It's easy for principles of one era to be an ill fit for another. It's easy for the original ideas and principles to be fundamentally flawed in ways that no one could or was willing to admit to.
"Running with it" can be dangerous. (Ask us how well Cold War politicking has worked out for us post-9/11.)
I think, at all turns, you must be asking yourself why you're doing what you're doing, and if it's actually effective. If it's actually good. I don't know that Jobs ever predicted that the bicycle for the mind would be beholden to OTA updates or have a commensurate attack surface exposure, but we have to deal with that reality, regardless.