How do you get a positional feeling?

Hey guys,
I'm wondering how to improve my positional feeling. When I play a chess game, I calculate very machine-like, sometimes including moves in my calculations which are completely ludicrous but I just want to find out why they don't work. Also, I very rarely see a position and immediately say : "Of course, this is the right plan here!". Do you acquire this feeling for a position just by playing lots of OTB games or do books help? I asked a friend of mine and he said those concepts should be taught by a trainer, because you then can ask questions and understand certain concepts more deeply.

It takes time to develop a position feeling. But you can make it easier for yourself by asking simple guiding questions. Like: "What pieces are good in this position?", "Where do my pieces want to be in this position"?, "How would a potential endgame look for me?" and so on.

Basically a trainer or a much stronger player who will patiently explain things is optimal.

A lot of people praise the Chessbase DVDs by Mikalchishin. Maybe I'll try them again myself. Last time I tried watching them I fell asleep, because of the boring presentation.

At your playing strength you probably won't get out much that you don't already know from the (german) Chessbase DVDs Planfindung and Variantenberechnung by Michael Richter. They are good for inexperienced, weaker players though. I found them valuable and think they helped me get above 1800 FIDE Elo.

But I still think that basically it is the right approach. Assessment and evaluation of the position. Identifying strength and weaknesses. And perhaps studying in depth the pawn structures relevant to your opening repertoire.

PS: I just started working with John Nunn, Das Verständnis des Mittelspiels im Schach. (Understanding Chess Middlegames) ISBN 9781906454388 (german) or 9781906454272 (english). Looks good too!

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Another good idea is to study high-level games featuring openings you play so you can see how middle game ideas plans evolve from the first 10-20 moves. Even playing through a lot of games quickly can be helpful. Of course you will encounter unfamiliar positions in your games sometimes, but if you play the same openings a lot, typical themes will tend to arise repeatedly.

#2 "How would a potential endgame look for me?"
Positional feeling comes from endgame knowledge.