Love your list! Have only read about a third of these. The rest go on my to read list. Meanwhile, let me add three more (with my comments) that I think should be on your list:

Understanding Media: The Extensions of Man by Marshall McLuhan. If you want to know the future of communication, learning, and work, this amazing book published in 1964, can open up new windows of understanding.

The Fountainhead by Ayn Rand. What is the source (or fountainhead) of human creativity? Although this is a novel, I consider it the best self-help book ever written. Continues to inspire to this day.

Atlas Shrugged by Ayn Rand. What would happen if man’s creative ability were to disappear? Rand’s seminal work gives the answer, plus an amazing, page-turning solution.