Best Book on Strategy

I would like to get your feedback on which positional book to tackle first:

Silman's How to Reassess your Chess or Nimzowhich's My System

How to Reassess Your Chess was pretty highly acclaimed when it first came out.  I'm not sure it accomplishes everything it set out to accomplish, but it does have many things to recommend it.  The central themes seems to be the creation of imbalances (and chosing the correct imbalances to create) and the visualization of achievable and favorable positions (and finding ways to create those vision, or fantasies).  Beyond that, it's the standard fare of static vs. dynamic advantages, space considerations, initiative, weak squares, weak pawns, etc. .. not much on over-protection though :-)

It's a good book, but not a light read.

I guess both are fairly advanced (I'm about 1600 ICC). I know Dan Heisman recommends reading the Amateur's Mind before reading Reassess your Chess...so I might start there.

Neither. Simple Chess by Michael Stean is the best. It's actually not 'simple' like 1200 level, but it's  the clearest, best explanation of strategic ideas with the best examples. 

I looked and saw your standard rating on here was in the upper 1600s.  That's usually about the equivalent to someone that would be about 1800 over the board (chess ratings here tend to be lower than actual over the board ratings).

That said, don't let the title scare you.  The book is really written for someone about 1400 to maybe 2200 (Jeremy Silman gives those numbers in his review of the book, it's not me making up those numbers).  It's called "Grandmaster Chess Strategy", which in essence is a book on middlegame ideas from Ulf Andersson's games.

It should immediately help your game.  For example, the first half-a-dozen to ten games or so talk about a concept that many players don't seem to pick up on until they are over 2000 and really should.  The concept of two weaknesses.  If a player has a single weakness, he can usually defend that weakness.  He may only draw rather than win, but when you are defending, a draw is satisfactory (knowing when to play for a draw instead of a win is a totally different issue).

However, once you have created two weaknesses, and especially if those two weaknesses are far apart, like say, weak dark squares on g5 and h6 around the Black King, and a backwards isolated b-pawn for Black.  Now you are spreading your opponent's defenses thin, and can often pull of a tactic based on overworked pieces in your opponent's camp.  If the Queen is the only thing holding the position together, then offering a trade, or forcing it to move to a different square so that it can't cover both weaknesses any more, could be the key to winning instead of a full-blown blast at the king!

Worth taking a look at in your case!

https://web.archive.org/web/20140708095832/http://www.chesscafe.com/text/review769.pdf

https://web.archive.org/web/20140708105648/http://www.chesscafe.com/text/review600.pdf

https://web.archive.org/web/20140708094414/http://www.chesscafe.com/text/smcs.pdf

https://web.archive.org/web/20140708094419/http://www.chesscafe.com/text/ammind.pdf

https://web.archive.org/web/20140708104258/http://www.chesscafe.com/text/review400.pdf

https://web.archive.org/web/20140708093410/http://www.chesscafe.com/text/review812.pdf

I think Reassess is the #1 most overrated book out there. PARTICULARLY the early edition which got a lot of good press. 

Seriously, he starts off the book with the Lucena position, and says beginners should learn it. Are you serious?!

Then he doesn't warn that his book is really aimed at 1800+ level players, and says beginners will learn a lot from it, and then goes into quite a few complex positional (not tactical) variations to illustrated some points. I was UCSF 1450 at the time, and despite hammering at that book for several weeks, I got almost nothing out of it. Too advanced. 

I understand he's revised it to make it more beginner-friendly, but if the content is similar, it was definitely NOT for beginners, or even 1400 level UCSF rated players. 

Simple Chess by Michael Stean is so much better for a new budding positional player (like myself). He avoids wasting time on crazy complicated sidelines, and gets right to the point, and it's very clear. Covers a lot of the same stuff, but much, much more elegantly.

The book has been substantially revised since then. I think that, somewhere along the way, he decided to put the endgame stuff in a separate book.