If you have the drive to learn about planning and judging positions, and if you have the time, please check the videos here
http://www.chess.com/blog/bladezii/my-annotated-games-and-my-chess-videos
This is based from my games and not planning for all positions. What plans you make and how to judge will depend on the type of positions you are likely to encounter based on what you play from the opening. That is just one aspect.
I hope I can help.
It's a hard question and books are written about these things. The simplest answer I think is that a plan is created based on the location and quality of pieces on the board. However to be able to make plans at some proficiency requires you to learn how to weigh these things. People usually read chessbooks about the different phases of the game to get better at this.
You can also watch games, lectures and look at games annotated by strong players. People usually reccomend middlegame books like "My System." I'm reading Lasker's manual of chess and I think it's good for beginners.
Here is an annotated game by two masters that might help you to see what they think about:
http://dadianchess.blogspot.com/2009/09/alekhine-on-new-york-1927.html
A)
This just takes experience in the middlegames that arise out of your openings and strategy/middlegame study. A lot can be read from the pawn structure. I recommend the books Pachman's Modern Chess Strategy and Soltis' Pawn Structure Chess. Although depending on how good you are (how good are you?) you may want to wait a bit. In general you try to seek play in the area of the board where you have chances. Biggest common factors are space and number of developed/useful pieces in an area. Thus the advice of centralization, development being so important, and attacking where your pawn chain "points."
B)
Not sure what you're thinking of when you say plan. But I always try to answer the questions, what are white's trumps / how can he play for a win and same for black before I do anything else. Forced re-captures you can't help it, but the idea is to foresee the forced moves and not allow any forced moves that undermine your trumps while highlighting your opponent's. IMO it's never too soon in the game to start asking these questions.
Plans may be very long in the endgame but in the middlegame they're usually short term or very general and are subject to change. Often an advantage transitions from one idea to another. A simple example would be the idea of pressuring his weak pawn turns into convert my material advantage (after you win the weak pawn).
C)
Ah yes, the infamous "need to do something" that so often entices less experienced players to self destruct their own position. Some ideas on what to do when feeling lost. Find the piece doing least for you (especially undeveloped or passive pieces) and improve its position. Find the pawn breaks and work toward playing one. If your position looks great and you don't want to change anything try making a plan based purely on what your opponent wants. Look only at his side... what does he want? Then make it difficult.
In any case don't take unnecessary risks. Keep your pieces centralized and active and king safe. Avoid the temptation of making (what amounts to random) pawn moves just to force something to happen.
"Biggest question")
I both deliberately think about planning and plans also come naturally. It's a bit like asking if tactics come naturally or if you think about them... it depends how difficult the position is! Sometimes I know exactly what my position needs to do, and sometimes I'm struggling to hit on the right idea. Sometimes the right idea is too difficult for me to find even if I had 100 hours for every move.
Oh, by the way, I have another thing I want to mention. I'm familiar with the "attack where your pawn structure points" advice, but sometimes it points toward the queenside, away from the king, and I don't get why I would attack when there's no king there. Also, how would I go about attacking that? What would be the goal of this?
Have you taken a look at some of the things suggested? Studied annotated games? Taken a look at the videos? Anything ?
Oh, by the way, I have another thing I want to mention. I'm familiar with the "attack where your pawn structure points" advice, but sometimes it points toward the queenside, away from the king, and I don't get why I would attack when there's no king there. Also, how would I go about attacking that? What would be the goal of this?
That's kind of like saying my opponent's pawn is weak, but why would I spend time attacking it if it's not near the king?
Queenside attacks aim to eventually win material. Sometimes you infiltrate / tie them to defense first.
bladezii wrote:
Have you taken a look at some of the things suggested? Studied annotated games? Taken a look at the videos? Anything ?
Yes, and you don't talk about formulating plans. Sometimes you talk about plans, but never how you arrived at them. I still don't understand what the goal of attacking on the queenside would be if it's away from the king. I don't think I've ever had a plan in a chess game to attack on the other side of the board just to do it. I don't get why you would do it or how you would go about doing it.
That's how you learn. A queenside attack is usually made to create pawn weaknesses on the queenside and attack them. Of course if you don't know what makes a pawn weak then such a plan would never really make any sense to you. Videos and annotated games can show you variables like these and other things you can take into account to make a plan. A Plan is based on many factors like king safety and pawn structure that I already noted. Learning about things like this will help you get better at making plans.
Maybe this will be helpful in learning about such things.
Both. It depends on the familiarity with the position. Usually it starts with a positional evaluation ("I'm slightly worse because my king is exposed", "His development is lagging", "this piece is doing nothing") and then it translates into a general objective and one or a couple of mini-plans.
But to find the details of the mini-plan(s), some calculations are usually required.
Sometimes, the evaluation and the general objective phase are skipped, and some mini-plan just jumps to your face because you've recognized some tactical/positional pattern.
And sometimes, the pattern thing is inconclusive, and you go into 'evaluation mode' again.
I like Silman's explaining of formulating plans, you need to find the differences in each camp, the "imbalances". If your opponent's king is out there in the open, your plan will be to attack it and remove its defenders. If your opponent has a hole in d5, your plan is to manouver your knight there. If all his pawns are in light squares, you should get rid of his dark squared bishop etc. If you can find these "imbalances" in a position, they will show you the way.
A) I can't tell what constitutes a reasonable plan. I don't know how to go about finding what my plan should be. How do you create different plans based on the situation?
B) I don't understand when you are supposed to use a plan. Some people say right when the middlegame starts, but often when that happens you are engaged in trading or forced responses to your opponent that take precedence at that moment. Do you wait to form your plan or do you form it first regardless of what is happening?
You plan right from the very beginning of a game you must have a clear direction and a roadmap in your mind of where your going if your not playing according to a plan the wheels will fly off your go kart and it's all over.
Recommended:
Find the Right Plan by Anatoly Karpov
http://www.amazon.com/Find-Right-Plan-Anatoly-Karpov/dp/1906388687/ref=sr_1_1?ie=UTF8&qid=1370979202&sr=8-1&keywords=karpov+planning
Everybody has a plan until they get punched in the face.
- Garry Kasparov -
Your "plan" can be to simplify through exchanges, and play for win via pawn promotion in the endgame, NOT checkmate in the middlegame.
That greatly cuts down on any "planning" required, to a very large extent. 
Otherwise, (as mentioned above), just find your weakest piece and try to improve its postion. In any case, (as a practical matter), plans will be forced upon you as the game unfolds.
Or play the Hippo. That opening "plans" is quite simple. But be prepared for crazy and seemingly clogged middlegames to ensue.
Around move 20, I started having no idea what to do and I did something stupid by pushing my pawn like that.
...Or play the Hippo. That opening "plans" is quite simple. But be prepared for crazy and seemingly clogged middlegames to ensue.
Firstly, as a hippo player, I am compelled to disagree. The opening does not actually have a "plan" except to turtle and wait for an appropriate counterattack. This means that my strategy will vary according to the opponent's moves, and I need to be ready for any pawn break (c5 against kingside storms/white d4-e5 setups, f5 against Austrian Attack/e4-d5 setups, b5-b4-N(d)f6 against long castling) or queen placement (I've deployed her to e7, c7, b6, c8 and a8 in various cases.)
My advice is use the hippo only if you know exactly what you can be doing in any white structure, and can formulate appropriate plans quickly.
OK. dpnorman's game. After 20. Qe2, let's look at the position. I'll try to write down my thought process.
Pawn breaks? ...c4. Looks hard to prepare, and doesn't do much. f5 is coming eventually. g4-g5 if white is brave.
Weaknesses? Back rank, e6 may be subject to lever. c2 is weak but hard to get to. Nd2 is for now sad and could be improved.
Pieces that could be improved? Nf6 is defending. Qc6 looks fine, but I wouldn't like trading after Qf3. White's pawns make the d8-rook look useless. No prospects on the kingside, so queenside? Double on the a-file, invade on the queenside.
Plan: Ra6, double on the a-file. If Rxa6, Qxa6-Qa2. If Qf3, Qb6 keeping the queens (esp. as white kingside may become weaker.) If Ne4, trade knights (and queens if allowed) then Rda8 with a likely R+P v R+P endgame that looks (cursory inspection) on the weaker side of a draw.
Mind you, this is only one plan. Basically, analyse the position's static features, think of some likely continuations and improvements, then evaluate the results. Pick the sequence that looks best for you, and that is your plan.
Plan when there's nothing to do.Now you can apply those strategy books you read at leisure.
Ok I will try to note things that I think are important at move 20.
White's king safety looks pretty bad due to the weak dark squares around the king made by playing the move h3. In fact White has dark squared weaknesses everywhere. All but one of his pawns are on light squares. Black's king has to watch out for backrank tricks.
Black has a 4 vs 3 pawn majority on the kingside and White has a 3 vs 2 but pushing the d pawn forward might be hard because it requires White to play a move like c3 which makes the d3 pawn a little weaker.
The a-file is open but I don't know how useful it is for either side, White's d-pawn is on a semi-open file and Black's e-pawn is on a semi open file. Both sides have two pawn islands.
Both Black's knight and queen are better placed but I don't think they are working well together while White may be able to get his pieces working well with ideas like Nf3-e5 and f4-f5. Then the knight will be protected by the queen and the knight and rook come together to pressure the f-file. I don't see any way for Black to improve his knight but the queen can be improved. I am not sure about the situation of the rooks on the a-file but my idea about them getting easier to see now.
Nothing is hanging.
White's weak squares seem to be the dark squares but Black has a problem on e5. This is a good outpost for an enemy piece as a move like f6 has dangers.
With all this I think I have White's plan.
White would like to improve the position of his pieces. An old Russian rule is that if there are no threats in the position then you take your worst placed piece and improve it. So a good plan is Nf3-e5. The knight would be well placed on that weak e5 square and there it targets f7. And White just happens to have a rook on the f-file! With this plan White's pieces become better placed and he starts working on Black's weaknesses and his own strengths. So if it were White to move Rxa8! would look good to me. This prevents Black from screwing with the f-file plan and the rook on a8 i think has no real threats. This would even decrease Black's piece coordination. Next White would play Nf3 which for the time being covers those weak dark squares. But it's Black's move.
It is hard for me to find anything fantastic for Black other than the idea of improving the pieces. One thought is to put the queen on d5. The queen is more active here and there is the threat of Qd4+ attacking the dark squares and that rook on a1. Black has to be careful because this move leaves the b5 pawn hanging. But I also want to stop White's plan of making Black's pieces worse and improvng his own. So 20...Rxa8 21.Rxa8 Qd5 is my idea. Then White will probably play 22.Nf3 continuing with the plan at a slower rate or maybe even a better move like 22.Qe3 covering the dark squares and the hanging f-pawn with the queen. That move has a plus of eyeing the c5 pawn. After either of these moves a continuation like 23.Ra5 looks dangerous as it's hard to defend that b5 pawn.
So I kinda give up and think 20...Qd5 is the way to go. Although Black's rook has no possible threats on the a-file White's rook does.
After 20...Qd5 21.Rxa8 Rxa8 22.Nf3 I'm out of active ideas. So here I think that a continuation like 22...Rc2 is good waiting for something like 23.Ne5 Qd4+ 24.Kh2! Ra1 when Black can attempt to trade rooks and head for the endgame where White's knight won't be as dangerous. But even then White might try 25.Rf3 so the whole thing looks complicated to me.
I don't know how accurate all of this is but hopefully it was helpful.
Learning how to plan is a complex topic that many books have been written about. My advice is that you take a look at some of them. A basic place to start though is thinking about where your pieces are placed. Find your worst piece and put it somewhere better. Another idea is to look at the imbalances in a position. Jeremy Silman wrote a fairly big book just about this that I would recommend.
I read your earlier post about not understanding the purpose of attacking where there isn't a king, and I think this mentality of always needing to get at the opposing king is stopping your ability to formulate plans and assess the positions on the board. There can be different reasons for a queenside attack, but the most simple would be winning material. Winning a pawn or two can lead to a winning endgame. You don't need to checkmate in the middle game to win a game.
Finally, while I'm not quite 1800+ (as of posting this my rating on this site is 1704), I think that whether plans come naturally or If I have to think about them depends on the position. If I'm familiar with that type of position I usually have an idea of what to do already. Other times even if the position is unfamiliar certain ideas such as open files, weak pawns, and knight outposts stand out and I can make plans easily. Some positions I really have to think about what to do, and even then I might be clueless. It all depends on where the pieces are on the board.
It will be difficult to answer my questions because planning a general idea, not a concrete concept, but I hope you guys can help me a bit.
A) I can't tell what constitutes a reasonable plan. I don't know how to go about finding what my plan should be. How do you create different plans based on the situation?
B) I don't understand when you are supposed to use a plan. Some people say right when the middlegame starts, but often when that happens you are engaged in trading or forced responses to your opponent that take precedence at that moment. Do you wait to form your plan or do you form it first regardless of what is happening?
C) I will show a concrete example later of a real game where this happened, but I often have positions where nothing seems obvious and the only things I can seem to do either wouldn't gain me anything or risk too much. This happened to me today. I had no idea what to do in one of my games and I just kind of waited for my opponent to do something since I couldn't do anything. Finally, out of a desire to do something, I decided to try a cheap tactic which would gain me a lot if successful but ended up losing me a pawn and the game. I didn't know what else to do in that situation; the game wasn't going to suggest a plan itself.
I guess my biggest question is, to you 1800+ players out there, do you cognitively think about planning or do plans just naturally come from the board? Is it obvious what plan you should have for each side or do you have to think about it a lot first?
I can't post the game yet since I'm on an iPad but it was a loss that was directly related to this. In the meantime, please answer the questions and I thank you for your help :)