Thinking more like Nimzowistch

Whilst we read many times in other people's game the importance of prophylaxis, it's not till we experience it ourselves that we appreciate the necessity. Playing on the Black side of an Advanced Caro Kann, I reached the following position with Black to move.

As Black, I have achieved been able to exchange off my bad light squared bishop, control the c-file and am looking to exploit White's advanced Kingside pawns.

I did not want to commit with ... Ned6, as I saw the possibility of ... Nc4, Nxc4 dc which would create an outpost on d5 and a Queenside pawn majority. I chose this, not thinking Qa4+ and Qxa7 was possible due to the trapped piece. However, I missed White's move.

The Right Endgame plan?

In the following endgame position it is Black to move. I played 39. ... g5 and my opponent resigned. Interestingly, when I put this through Fritz, it assesses the position as level. If 40. hg fg then Black obtains a passed Kingside pawn, coupled with his passed d-pawn and the advance of the b-pawn. Black's bishop can not be evicted from f8 and I think White is clearly lost.

My Game Annotations and Analysis