The future is going to be new, and different, and it is hard to predict. Your phone (for some definition of phone) can give you answer to nearly any fact based question you can imagine. Right now, in under 500 mSec. The future doesn't look different when its entered into gradually, it looks hugely different when it is punctuated.
So if Taleb really wanted to 'check' on his futurist mantra, he should pick a number, 10 years, 25 years, 50 years. And then 'spend a day' in that time by removing everything in his possessions, environment, and activities that were not created or possible at that previous time.
I would predict that its a matter of opinion as to whether the future is or is not 'cool', most people would agree that the past sucks. :-)