Alan Kay has agreed to do an AMA today

I'm not Alan, but I saw one of his talks[1] about how they did invent all those things we're using now, which you are very much referring to.

What he said was important was to have a big horizon, at least 10 years. Anything less would not do.

Then envision what should be possible in that time. "It would be ridiculous if $X wasn't possible in $Y years" and then backtrack on what would technically be required to make that happen.

Rinse repeat. He said that with good company support and a good team, you often found yourself delivering at half that time none the less (but again, you should never constrain yourself to that little, or else you will stress towards performing, instead of thinking properly about the problems needing to be solved).

Alan: Hope I didn't butcher your message too much :)

[1] I think it might be this one, but I honestly haven't checked. See it anyway. It's a good talk. https://www.youtube.com/watch?v=NdSD07U5uBs

Seems like a good a strategy as any. :) Thanks for the pointer!

10 years is too close -- 30 years out will generally lose the pernicious connection to the present and "how do we get there?". The idea is to "go out there and bring the ideas back" rather than try to go from the present to the future.