How did Black lose the initiative? What are some key factors I mis-evaluated, or failed to notice?

This was a correspondence game I played (I don't use opening databases, or analysis boards. I prefer to test my calculation ability and simulate OTB games if possible). I was Black and I felt a bit clueless at at few points in the game. Where could I improve and where did Black's play go? I didn't feel I had enough compensation for my material deficit. Any analysis, or thoughts, would be appreciated

(Starting from 12...Rc8 ) .

12...Rc8 dont seems bad actually.

Point of 12...Ng4 13.h3 Nh6 is white lose some tempos due to knight on g5 . After 14. Ne4 f5 , black can use their center and pieces to organize an attack, probably on kingside. 14.h4?! Seems bad in spite of 14...Ng4 , followed by h6 and f5 (pawn on h4 is target , too ) 

After 12...Rc8 13.Nc3, the reason Ng4 being better is it conserve pieces on the board.  White more or less is forced to play Nge4 , and now f5 is playable w/o exchanging knights. (It is important because black has some attack chances on kingside and white has some space problems) 

16...Rc6 and  18...Re6 had same idea: Rg6 . In 18...Re6 , Rg6 is already a threat , though white is probably already better . 16... Rc6 if black can play Rg6 attack gives a great iniative: h3 is en prise,  Bc6 is a threat  , not enough defenders etc etc. For example, let's look what happens after 16...Rc6 17.Qxe5 (no mark because I didnt analyzed it yet, though It seems bad on first glance ) 

17...Rg6 18.Kh1 (18.Qe3 lose after 18...Qa8 19.f3 Bxh3 20.Qf2 Rxg2) Bc6 19.f3 Bd6 and qg5-qf4's are coming , I am unsure about final evaluation of that position though black definitely have more than actuel game.

I think your main mistake was approaching that position like Benki gambit , or any other variation that black only lose 1 pawn . At there , if black have some pressure and iniative , or some positional advantages,  it could be enough to keep balance. But you were 2 pawn behind,  and need to be more ambitious, you know that iniative would be enough to keep balance by heart, and you should have search of ways to show them instead being satisfied with small positional advantages.

EDIT:typo fixed.

I studied the analysis from above and covered my mouth, because my observations are insignificant in comparison with it

13...h6 and 14...Re8 felt really slow. You're two pawns down so you don't have this luxury.

Ng4 is the same idea as your h6... it kicks the knight. But Ng4 is more active because you're getting out of the way of both your f pawn and bishop.

Yeah, Rc6 for Rg6.

That's my impression. You gambited some material, then played slowly so you had little compensation.

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13... h6? In these kinds of positions, Black usually wants to kick the White Knight back. The computer believed this was a mistake and that ...Ng4 was preferred. Could anyone be so kind to explain the reasoning to me. The move ...Ng4 looks weird to me: it looks like I am prematurely attacking with the lone Knight.

White Ng5 don't put any danger and could be targeted by Be7 and the Queen. Why spending a move to help white re-group with Ng5-e4? I would play Bc6 and if Cg5-e4, then Cf6xe4 and f7-f5. Also interesting it seems to me 13...Rc8-c4 with the ideea Bc6 and Rg4. Agree that you should speed up things a bit.

I agree with the post above. To me the natural continuation to develop the initiative is 13... Bc6.

Check out Tal's games.  You can learn so much just from analyzing each move. It's a dance. If he sacrificed three pawns and pulled his queen out that early, he would keep up the attack full speed. 

It seemed like you attacked and then retreated. 

I love studying his games. 

Obviously a more seasoned player can give you a more detailed instruction,  like SpaceySmile, for example. I always learn so much from his forum analysis sharings. 

And great personal annotations on your games. They're priceless in learning! Cheers. 

I think your main issue is you don't understand the principal of maximum effectiveness. Generally speaking, the more useful thing a move accomplishes, the better it is. Useful could be in making threats, improving your piece activity, or preventing your opponent from fixing a defect in his position. 

For example what did Rf8-e8 accomplish? What did 11... O_O do? What did Be7-c5 accomplish?  None of these moves threatened anything. All of these moves were the equivalent of saying "I pass" and let White catch up in development. There's a great blog post on this principal here:

https://www.mark-weeks.com/aboutcom/aa06b18.htm

Second, you didn't have a plan. Ask yourself, "How am I going to win this game? What are the imbalances in the position that favor me and how can I use them. 

After White's 11th move you have open lines, a lead in development and more space. Your opponent's king is temporarily unsafe in the center, his knight and queen are both misplaced and subject to attack,

Your plan should be to keep making threats on every move, to keep him occupied and prevent him from gaining the time he needs to complete his development. It is especially effective to exchange off his active pieces, if you can do it with tempos.  You have already invested some material, this is the time to invest more. The first move to consider has to 11....  e5-e4.  After 12. Ne4 Ne4  13. Qe4 O-O you have open lines for two bishops a queen and a both rooks to attack his virtually undefended kingside. After 14. O-O  Re* is going to come with tempo, due to discovered threats on the queen when the bishop moves. Black has open lines for ALL FIVE of his pieces  You just keep kicking the queen as you move your pieces into  position to attack his king. This game is basically over. 

You might want to look at some of Paul Morphy's games to see how to play when you are so far ahead in development.

Good luck.

Thank you for taking the time to share your expertise. 😊

I was just looking at a Tal game, in detail, just last week. I agree, Tal has an instructional style. What impresses me time and time again is Tal's calculation ability; it is often overlooked by his sparkling combinations and deep positional moves, but they are all connected.

Thank you for the feedback on the game and especially the article link on "Principle of Maximum Effectiveness." Similarly, I've known (for a while now) some of the benefits of remaining flexible in a position, but this "principle" takes this concept in a slightly different direction I hadn't heard before.

And yes, perhaps I should study Morphy's games a bit deeper. Admitting, I am familiar with only a few of his games. Funny because a chess buddy of mine is fascinated with Paul Morphy's games and Morphy has always been his favorite player. Maybe I should look into it some more too  

Tal himself says that not all his combination moves are based on calculation; sometimes he go by instinct. You want to improve? Not only watch the games, but train yourself. Find a suitable combinations book and solve it. Btw, no need to thank me..

Here is one patzer's view. I think the reason 13....Ng4 is better than 13...h6 is that pushing f5 is an important strategic goal, and 13...Ng4 lets you achieve it efficiently.  Although you have a development advantage for your pawns, White is castled and has no glaring weaknesses, so you are not going to mate him with some Morphy-style piece attack.  You need to use your pawns to grab space and open lines for your bishops and rook. After 13...Ng4 14.Ne4 f5 15. Ng3 e4 I think you have a terrific initiative. 

Your compensation is of a temporary nature, and if White is able to develop successfully his two pawns will win. In fact, after 15.d3 I strongly prefer White

The difference between tactics and strategy is instinct. I came to learn this myself, but when I lived near Bruce Pandolfini in NYC (he introduced me to chess after I was hit by a car and lost my professional music and photography career). Bruce and I used to talk about the game; it's similarity to in depth music theory theory:  students who have no natural insight nor instinct will have a much harder time excelling... at anything that requires use of intellect. Tal's talks about this in his autobiography. It's universal. But with regard to chess,  instinct is a must. Intuition comes into play,  too, but that's on a much more visceral level. 

As far as books go,  I'm confused (not really, just making a point), yesterday you were getting on my case about how you taught yourself and didn't need any outside help., including books.  I mentioned studying Chernev's timeless tome on positional play,  and you got on my case about that. Bruce gave me several of his puzzle / tactics books, as well as Josh's, which I studied and completed just for fun (I enjoyed the challenge  of solving the puzzles and challenges while going through 4 years of PT and surgeries). Plus,  an important thing Bruce said was solve them without a board; in your mind. (Coincidentally, this is how im still able to write instrumental music without touching an instrument. You have to know your "instrument", in this case,  chessboard, before studying positional play or games, e.t.c. )

And just because I don't play other people yet,  as I've stated,  chess.com has my rating listed as too high. It's not fair to another player to expect a good match and then just obliterate me in 20 moves.

It's the difference between studying music (which I did without a teacher when I was a child) and then knowing when you're ready to start your first band or quartet or whatever. 

Just because Im not there yet does not mean I can't comment on this thread. You said you weren't talking to me; there's no one else you could have been talking to. 

@keSatoKaiba is a published writer in the chess genre. His website is lovely and has wonderful material to help one learn the infinite and lifelong approach to studying and self analyzing one's games, and other's. (The Analysis Board is absolutely not  a waste of time. I just plugged in a game I played 7 weeks ago vis the Dutch Opening. I've practiced so many puzzles, which,  of course,  help one recognize patterns [just like studying chord variations and inversions as a part of a student's time in the Woodshed (practice room), help them pick appropriate and fascinating choices while improvising in a jazz quartet or whatever, without having to think. It's ingrained in their minds. This gets back to instinct, and,  as you say,  why it's so important to have books at the ready to tactics, strategy, e.t.c. I found Bruce's books to be helpful. Now I still do puzzles, tests,  and challenges, daily,  but Chernev's books,  as stated two days ago,  help with understanding positional play/analysis. 

I was I suppose pleasantly surprised that when I plugged the PGN into the Analysis Board this evening,  I finally discovered how I achieved checkmate so swiftly-- not fast, but before I had expected:  I employed the tactics and patterns I had ingrained in my brain for years--I had four pieces attacking the King, and I knew I had check in 4, but there was something about that game I always wanted to study, which was beyond my personal knowledge. So I compared my notes to the board's and, again, was pleasantly surprised at how much more I knew but didn't realize. It's a learning curve. For you to say , as you did,  that I'm not learning the right... ha!  Bruce and Garry are no slouches. I think I'll take their advice and my instinct... and plus the main reason I study:  because I've always been an autodidact and I love studying chess as much as I love playing. 

@keSatoSaiba Studying Tal's games in depth, chronologically,  is actually what made me decide to plug in one of my first "good" games (ha! relatively speaking)  into the Analysis Board. I wanted to double check my own analysis. I discovered so much about my playing. What I need to work on, but also, continue going in the direction Im going in on my endgames.

Thank you for that brilliant link to the positional play article.

Thank you for inviting me to your club; I look forward to learning much and enjoying the process fully! 

Stay strong, everyone! 

(Please excuse any typos; I'm only on my one using one finger. Tried my best.)

Optimissed writes

"On general principles black shouldn't give up the second pawn. .... When you give up a second pawn it improves white's options. For instance, he can give up a piece for the third pawn and the initiative." 

In general you're right BUT In the opening, and especially when attacking a compromised king position.. giving up multiple pawns for rapid development and OPEN LINES  is FREQUENTLY the right idea. This opening is a classic example.