Knuth's "The Art of Computer Programming" - linked lists, state machines.
Carlos Castenada's Don Juan series (yes, I know it was fiction) - "one has no choice but to believe. What matters is what you believe".
John C. Lilly's "Center of the Cyclone".
These three, all around early-mid 70's, ended up moving me from the UK to Los Angeles. Strangely, each adds a different understanding to the others. Together, I guess it just makes me a bit strange. But it works.
The Black Swan (anything by Taleb really), Meditations by Marcus Aurelius, Letters from a Stoic by Seneca, Epictetus' Discourses, Fish that ate the whale by Rich Cohen, Man's Search for Meaning, Titan, Principles by Ray Dalio (not really a book, but really worth reading, plus it's free), 4HW by Tim Ferris, The Strategy Paradox.
Also Teddy Roosevelt's biography has been very influential.
A rather unfortunate title for an amazing book. You might think most of what it says is common sense, but in reality, ever since I read it, I've been far more cognizant of relationships with people & despite being a talkative extrovert, I have tried my best to shut the hell up and listen :)
I believe the title is even better now than when it was written in the 1930s; the fact that when most people hear it they think of Machiavellian back-stabbing is evidence how important its lessons are today.
On Being Free by Frithjof Bergmann changed my perspective on what work should be for an individual in a society. It's not very analytically heavy and is definitely a great read. I also met him and what he is doing around the world is pretty amazing.
I still remember how he told me in 2005-06 that 3d printing is going to usher in a whole new idea of what work should actually be. I was a engineering student at the time, quite obsessed with the room-sized 3d printer and could not fathom exactly how that would happen. Well I guess it is starting to at least.
The 4-Hour Workweek by Timothy Ferriss. He is some weird combination of crazy person, scummy used-car salesman, and genius. The best idea from the book is his "dreamline" idea, and I have been doing it since around 2009. It really helps you focus your effort, and get rid of tasks that don't accomplish your goals.
I know you mentioned that he's part scummy, used car salesman, but when does that part go away? You really shouldn't open a book that you actually want people to finish with 50 pages of boasting about how naturally awesome you are at literally everything, and how your life is a perpetual cycle of falling ass-backwards into giant piles of money and women. There are actually a ton of books that start like this and most of them don't contain anything of value, so I assumed that this one was the same.
I don't read nonfiction the same way most people do. I do multi-pass. I first read the table of contents, then skim the intro pages for each chapter, then skim the whole book, and then finally actually "read" the book. It is weird to people who are used to only the last part, but it lets you see the whole picture beforehand and most importantly it lets you know where to pay attention the most.
Ferriss does that stuff because he wanted to sell books as much as possible. He even chose the name of the book by a/b testing. That stuff is line noise, and I am sure he knows that it is, but it sells millions more copies because of it.
So I would say try the reading approach I mentioned. There is a lot of filler, but there is a lot of good content. I would say the most useful thing is the dreamline idea, it a good approach to goal definition, a lot better than any sort of bucket list and such. I do it somewhat differently than he outlines in the book, but I still do it every month, and it has helped me accomplish a lot more.
"Four-Hour Body" is also very much worth a read. Both the methodology he uses and the ideas themselves are useful - and our bodies are a pretty big part of our lives.
Haven't read "Four-Hour Chef" yet, but people have recommended it for the stuff on learning.
ActionScript programming (2004?). My first programming book. Why ActionScript? I can't remember. But being introduced to OOP in my early teen years was fuuun.
The Lean Startup. I just randomly got it and read it. I was going to go into game development then after reading it I totally changed what I was going to do.
untethered soul - after 15 years of reading about meditation and "inner freedom" this book explains things so clearly, direct and obvious that I feel I have made an important step forward. Right after finishing it I re-read most parts again. It was the right book at the right time for me. I guess many readers might find it indeed too simple but for me that's the strength.
Carlos Castenada's Don Juan series (yes, I know it was fiction) - "one has no choice but to believe. What matters is what you believe".
John C. Lilly's "Center of the Cyclone".
These three, all around early-mid 70's, ended up moving me from the UK to Los Angeles. Strangely, each adds a different understanding to the others. Together, I guess it just makes me a bit strange. But it works.