Struggling to evaluate positions!

I'm really frustrated because I feel like I'm doing everything right and (think) my positions are great but when I analyse later with stockfish, I see my position was NEVER better in the first place. Its annoying because if I can't even tell the difference between a good position and bad one after a year of playing, how can I possibly improve? Even seemingly simple positions I seem to evaluate wrongly and I don't know why.

Take the following position, for example:

To me, it seems like black SHOULD be better slightly. Black's bishop is eyeing a lot of squares. Black has far more space with their pawns that are all defended in a chain. Black has an open file for their rook.

White, on the other hand seems to be a little "stuck" with their bishop as it doesn't have many squares and has far LESS space on the board. The only advantage is maybe that white is castled and (perhaps) black's doubled pawns are bad?

Regardless, it seems like black is better or at least equal, so why is white +1 here? What am I missing when evaluating simple positions?

Ok I'm not going to give you a detailed analysis of the position, because it's actually beyond my (2000+lichess) pay grade. A couple of pointers to your thought process though:

Why would you assume it's a simple position in the first place? Something you can easily work out? I can't, and I'm quite a bit higher rated. It's a middlegame position that's about to get messy in the center. Chess is a complex game.

You generally focus too much on the static side of things. You notice black has the h file, fine, but is that rook going anywhere? What's there to attack?

As you pointed out, black didn't castle yet. Now, go one step further. Is black castling short or long? In both cases, how does your perception of that pawn chain change? Is that kingside stable enough for short castling? What'd white do? If 0-0-0, is black able to start rolling the e f g pawns down the board and crush white OR is the d4 pawn actually more mobile? Is it safe for white to play c4 at some point?

There are always many things to consider, and I'm sure a stronger player would come up with more and better questions.

This is not an easy position to assess. When I saw e4 I knew it was dubious but I struggled to find a clear-cut explanation, this was just an intuition provided by years of experience in similar situations. After five years of competitive chess I would not have been able to assess this position correctly.
Also the lichess engine paints a slightly dark picture; Stockfish 15 at depth +30 gives e4 as 0.6; only 0-0-0 is better but still not completely equal.
The best explanation I can give is that e4 rigidifies the pawn majority on the kingside, and with the given piece placement and pawn structure it is a problem. The Be3 controls solidly the f4 and g5 squares and White will play g3 and h4 next to prevent any pawn advance. As Black has doubled pawns, the plan h6-g5 then f4 is not available anymore, and when the pawn is at h4 the open h file is quite useless. Meanwhile White has a mobile majority and will play c4 and d5 at the right time to get an advantage in the center.

One thing you're not evaluating is king proximity. Black might have more space, but it's far away from the White king. What attack can Black generate from here? Whereas White has a queen on the Black king's file; a simple f3 creates a king attack. Without a means of creating an attack, I think Black is actually pretty cramped.

Defense-wise, Black's pawns are weak on both corners, the bishop and queen can attack the b and a pawn, and the g pawn is hard to defend long-term. White has pawn weaknesses as well, but the g side can't be reached by anything Black has, and the a pawn is soon defended by the king, with no easy way for Black to create heavy pressure.

Pawns know no true allegiance; that Black pawn chain may well work in White's favor if they plant their bishop on g5, preventing the long castle. You're looking at a bishop trade.

There's also tempo. Nc4 attacks the Black bishop, and where does it go? It can't stay on the h2 diagonal, so it either leaves it or dies. Once it leaves e5, the knight can jump there, attacking the queen and demanding a trade that will get White's pawn to e5 and open up the d rook, again cutting off the long castle.

For general improvement tips, I always recommend watching Titled players explain positions in Grandmaster games, they're very good at saying why positions are good or bad. There's also ChessNetwork's instructional video on Chess Holes; he's kind of hard to listen to but he's got good advice.

Thanks @Nerwal and @ShiningDrongo and @dnowmects, it makes me feel a lot better that positions like this can be tricky for higher rated players as well. I also really appreciate your detailed feedback and interesting insights into where white's advantage may be coming from.

You guys are great enjoy your week

@basmik said in #1:
>after a year of playing, how can I possibly improve?

lol Hey, this ain't tic-tac-toe. It takes years and years to develop any great proficiency at the game.

Assuming white doesn't have anything better, at the very least 1.f3 will make it impossible for black to maintain a pawn on e4. There are no pieces for black to defend it with and many for white to attack it with! The uncastled black king prevents the otherwise strong response 1..f4.

The engine suggests that 1.Kb1 and 1.Nc4 are ways to maintain an advantage, though. It's hard for me to see why. It looks like one idea after O-O-O is d5, kicking the knight, and maybe Bxa7 b6?? Qa6#.

So, for a start, I'd like to say that I think that +1 is a bit too much for this position. If you click around some more and let the engine play a couple more moves, it tends to dip down to somewhere around +0.5 to +0.7 .

More importantly, for someone who is a relative beginner, I'd recommend not focusing on engine evaluations too much. When two players play over the board, neither of them know the engine evaluation (unless of them is called Hans) and what matters are the practical aspects of the position. Which side is easier to play. Many "dubious" openings like the Benoni, the Dutch or even the King's Gambit are perfectly playable at every level except the very highest, despite the fact that if two engines were playing, every game would be lost with such an opening.

Now, when it comes to evaluating positions, this is a difficult question even for extremely strong players to answer. I've been playing chess for almost 20 years, so at this point, I don't break a position down step-by-step and assess each factor. It comes naturally to me. I stare at a position for 5 to 30 seconds and my instincts give me a rough evaluation.
While you're still learning though, there are key factors to keep in mind, such as:

-King safety
-Piece activity
-Pawn structure
-Space advantage
-Bishop pair

And I gave this in a rough order of importance, highest to lowest, although, this can vary wildly depending on the position and is in no way a definitive list.

Some positions simply can't be evaluated by the "naked eye" method of staring at it and letting your instincts tell you the eval. Some simply require calculation, because in order to reach a definitive conclusion you have to see not only what is but what will be.
For example, in the position you gave, you say how Black has an active bishop, and they do. However, Nc4 is coming and the bishop will be under fire. If it moves, say to e7, then d4-d5 will create a large problem for Black's knight on c6, which will be very short on good squares. And if it doesn't move, which it shouldn't, then it gets traded off, White still pushes d4-d5 and brings their bishop to the beautiful d4 square. Based on this development, we can conclude that Black will be more or less forced to castle kingside, after which their far-advanced pawns will be more of a weakness, and a hook for White to launch an attack (with f3 or h4-h5 for example) rather than an asset in gaining a space advantage.

This is indeed quite a tricky position and I can easily imagine even grandmasters misplaying it, so don't feel too bad about not understanding it immediately. Chess is a learning experience and things that feel like a struggle now will eventually be second nature to you.

Good luck!

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