The Basics of Planning

 There are few things more frustrating in chess than not knowing what to do.  Take this position:

We're Black and we have a nice position: White's played a non-critical line, we have the two Bishops, equal space and no real weaknesses... but what do we do next?  Maybe ...Bg4?  But after White plays h3, we either exchange, losing the Two Bishop advantage, or retreat and likely end up on g6, where we stare at White's pawn wall.

That's not great.  Maybe ...Be6?  Okay, definitely a better spot for that Bishop, but now our Rook is blocked and our Bd6 is stuck defending e5 like a pawn.  That's not ideal, either.

Hmm, maybe we can ask a different question: which side of the board should we plan on?  We have more space on the Queenside, so maybe we keep pushing those pawns.  That looks decent.  The Kingside might also be an option: ...Nh4 and ...Bc5 create pressure, and maybe ...Bg4 now provokes some weaknesses.  That also looks tempting... but should I be doing any of these while most of my pieces are undeveloped?

This thought process goes round and round.  It's easy to get bogged down and never get anywhere.  We have an abundance of options that all look equally plausible.  Sometime we don't even recognize the options and we draw complete blanks. We stare at the board and nothing comes up.  We have no plan.

I would like to offer a solution, or at least a partial one.  When in doubt, focus on the most essential things.  These might not be "perfect" but are very rarely wrong.  From there, we can slowly add in more complex concepts.  Treat this as a basic introduction to planning.

The Prime Directives

What do you do in the opening?  If you've followed me for any length of time, you know the answer: develop your pieces.  Attacking, winning material, getting a better pawn structure, these are all nice things, but they are secondary to development.  In the opening, it's never a mistake to develop your pieces.  That's your prime directive.

Yes, "prime directive" is just an excuse to reference Star Trek.  I'm not ashamed to admit that.

Each phase of the game has a similar prime directive.  The opening is about development, the endgame is about promotion, and the middlegame is about attacking weaknesses.  This is a simplification, but it's a useful one.  If you played a game where you developed your pieces in the opening, used them to create weaknesses and attack them in the middlegame, and then focused on promoting your passed pawns in the endgame, that is a perfectly logical game of chess.

If you don't know what to do in a position, start there.  Let's apply it to our position.  The best move, according to Stockfish 16 at depth 40, is a -0.4 evaluation.  I'll come to that later.  For now, we have a piece that is not developed, so let's develop it.  10...Be6 is evaluated at -0.2, and so is 10...Bg4.  They aren't the "best" moves, but they aren't mistakes.

Now that we are fully developed, we can probe for weaknesses.  Nh5-f4 makes a lot of sense, especially if we provoke h3 from White.  We likely force White to exchange his Bc1 for our Nf4, and then powers up our dark-square Bishop.  Maybe a Kingside attack could come.

Is this the "best" plan?  Objectively, no, says the computer.  Is it easily understandable and we could come up with it quickly, only looking at a few concepts?  Yes.  Mission accomplished, in my eyes.

Going Deeper: Improving Pieces

We can add a further layer to our analysis.  In his books, Fred Reinfeld often listed the best squares for each piece and the roles they would play in the coming middlegame.  We can copy that approach and use a very simple itinerary:

• Rooks need open lines
• Bishops want open diagonals
• Knights do best on outposts
• The Queen feasts on weaknesses
  
• The King should be kept safe

We have two ways of using this information.  First, we can think conceptually and ask, "If I could place this piece anywhere on the board, where would it be?" Here, there are no true outposts for our Knight, but both d4 and f4 look strong.  Our Bishops probably want to go to e6 and c5.  Our Queen doesn't have any weaknesses to attack yet, so she probably stays put for a bit.  Similarly, we only have half-open files, so our Rooks will either go to the center (e- and d-file) or keep one on the a-file in case that opens up.

That is an excellent first step.  Second, we can use these same ideas to figure out how to further improve our pieces.  If we can provoke White to play c4, for example, then the d4-square becomes a great outpost.  If we exchange pawns, we get open files for our Rook: that's likely possible by playing either ...f5 or, more likely, ...b5-b4, perhaps with ...a4 played first.

This, then, gives us a pretty decent plan: put our pieces on these squares and then push the Queenside pawns.  That's the best plan, says Stockfish.  We still need to find the best way to do that, the concrete move order, but at least we have a plan.  We are no longer staring at the board blindly.

Speaking of staring blindly, this position is taken from a blindfold game I played against Stockfish lvl2, and I more or less followed a version of this planning procedure to reach this decision.  You can watch the game below, where the first 12min or so leads up to this position.  Interestingly, the computer played a very early h3, which caused me to change plans and immediately induce a blunder. I don't know how interesting this is, and I did not record this as instructive content, but it's a real-world, unfiltered example.

Going Further: Next Steps

The above is an excellent foundation for planning, and it's probably sufficient for anyone under 1600 or so.  The basics are the basics for a reason: they work in the majority of positions, so you can rely on them for a long time.  That said, if you want to go further, I'd suggest looking at the following.

First, pawn structures and common plans.  The two are basically the same, as certain plans (eg, pawn storms) are associated and work best in certain structures (eg, opposite-side castling).  Some pawn structures, like the Carlsbad or the Isolated Queen's Pawn, have entire books written on them.  These positions are especially interesting because both sides have very different plans, leading to rich positions.  The better you understand these, the better you will play them.

Second, deeper positional concepts.  Prophylaxis, blockades, good knights vs bad bishops, etc.  We can incorporate these ideas into our planning, getting more nuanced and really engaging with the strategical intricacies of the position.  

Third, imbalances. IM Silman famously endorsed this view, where you look at the imbalances, or differences, in the position and use that to formulate a plan.  In our example, we have the Two Bishops but our pawn structure is slightly worse.  We can thus try to maximize our strength imbalance (open the position for our Bishops) while minimizing our weakness (exchange or otherwise fix the pawn structure).

A lot of people really like Silman's work... and a lot of people don't.  Honestly, I've never read it, so I can't give an opinion.  I certainly like playing with imbalances, and I find it an interesting concept, but I'm not sure if I use the concept much in my games.  Definitely something to look into, though.

Conclusion

In chess, all the emphasis is on calculation, and rightly so.  That's the most important skill, but it runs contrary to basic planning.  Notice here that we were not calculating individual variations but rather taking a step back and noticing the general themes.  From there we conceptualized a plan and then used that to finally find the right idea.... which we can then calculate to see if it works.

It's a different process, and I think that's why people struggle.  They are trying to calculate a plan, if that makes sense.  If that's you, I'd suggest taking a step back and trying to look at these general principles and common factors first.  That should help guide you to a decent plan in most situations, and once you get some practice with it, you can explore some of the further steps mentioned above.