Is Chess Coaching Worth It?

I thought about titling this article "How to study chess middlegames" to fit into the series I started with Openings and Tactics, but I wanted something a bit more clickbaity. If you're confused why both those titles could work for this article, keep reading, all will be revealed soon...

The following is my own answer to the title question of this article, based on countless hours spent staring at the ceiling thinking about the best ways to improve at chess (I'm very fun at parties).

So, is chess coaching worth it?

My hot take: Yes, but mainly for helping you understand your early strategic mistakes in the middlegame.

Oddly specific, I know. Hear me out...

Let's say you want to improve on one of the following aspects of chess below:

Openings:
-> Compared to a coach, openings courses are much higher value per $ invested (basically semi-private, asynchronous coaching that ends up much cheaper because the author provides the analysis to many students at once).

Tactics:
-> Tactics trainers are usually free (ahem, looking at you, chess mafia).

Calculation:
-> Calculation is about practice, discipline, deep thinking, and correcting bad habits and mistakes in your thinking (coaches can encourage this but it's a deeply reflective process, and there's always something lost in translation when explaining your thought process to a coach).

White to move and win. See solution at the end.

Endings:
-> There's a wealth of books about endings, as well as free trainers, Lichess articles, studies etc.

Strategy:
-> Lot's of great books, videos, exercises etc. (when it comes to general guidance on strategic and positional play).

So, there are many good resources out there for most aspects of the game.

But what about the first mistakes you make after you leave your Opening repertoire? When you run out of moves you memorized or your opponent surprises you? The first point in a game when you're "on your own"?

Who's gonna help you with that?!?

Enter: "The Chess Coach"
An engine can help flag the mistakes, but it can only take you so far with understanding them. It works well for the blunders and obvious tactics.

But for the subtle positional nuances of the early middlegame, engines (especially for beginners) and AI/LLM explanations (currently as of August 2026, especially for stronger players) are not very helpful.

Why "the first mistake"?
The first mistake (i.e. strategic / positional mistake, not tactical blunder) after you leave theory is pretty dang high ROI (Return on investment) to fix with a coach's help.
Why?

1. You may reach the exact same position again (assuming you don't constantly switch up your openings, which you shouldn't!).

2. You will more than likely reach a similar position again. Even if you don't reach the exact same position, different lines in the same opening tend to repeat certain positional themes and plans.

3. If you don’t make the same first mistake again you’ll never see the same positions again where you made your second and third mistakes, etc.

4. As you fix more and more of these early middlegame mistakes, your first mistake will happen later and later in the game, and you'll start feeling the progress you're making.

5. Most people like to play chess more than they like deeply analyzing all their mistakes, especially from a casual blitz or rapid game. One key high ROI takeaway from each game feels less daunting. If you're the type who's more disciplined and wants to get the most out of your training, it goes for you as well, you're able to spend more time on the important mistakes in your games.

Why revisit your mistakes at all?
6. Mistakes from your own games are salient moments with personal meaning, so you'll be more likely to remember the idea when a coach explains it than you would for a random position from a book. This is called the self-reference effect: people encode and recall information tied to their own experience far better than generic examples.

7. Even if you don't ever see the same mistake or a similar mistake, the coach's feedback will help improve your overall positional understanding.

My hot take within a hot take:
Life is short. And chess is hard.

Studying game collections, the classics, or even the latest top-level games may not be the best use of your time in my opinion, especially as an adult improver with a busy life.

I think you can get far more ROI from analyzing your own mistakes, with a coach's help, in the openings you actually play.

Trying to understand every structure under the sun, every positional concept from every opening, and moves from other people's games you have no real stake in is a less effective way to improve.

That said, if you enjoy game collections and following the games of top players in detail, don't let me stop you. It's fun and it keeps you plugged into chess culture. I think there's also two exceptions to my advice: kids soak up everything so it's more worth it to go broad since they will likely switch up their openings a fair bit anyways if they stick with chess a long time. And pros need to stay on top of theory and their rivals' games regardless and tend to be able to compare and understand these nuances from different openings and structures more quickly, so it's lower effort to try to learn many ideas and structures from many different openings. The pros also benefit more from a broader repertoire where they are less predictable.

Still, this goes against what a lot of coaches say, to start with the classics and that game collections are a great way to study... Ok, it's getting too hot in here, I'll try to make my next blog a more lukewarm take. Moving on...

Putting it into practice:

Step 1:
Learn the Opening in depth:
-> If you haven't already done this, build an opening repertoire for both sides, or buy a few openings courses, and learn your repertoire inside and out.
-> Be sure to understand the ideas behind the moves and not just memorize.

Step 2a:
Practice the middlegames against an engine:
-> You'll want to play an engine a bit above your level, so you're losing slightly more than you're winning, giving you incentive to try hard to focus and win, but ensuring it's not so easy where you won't be facing the critical moves that you may see in your games.
-> The benefit of playing vs an engine is that it will be happy to play you over and over and over again in the lines from your course, whereas your friend Jimmy may get tired of doing this, or feel like you're just using him, and wish you'd help him study his openings for a change.
-> An engine like Maia plays more human-like moves, which can be especially helpful for training.

Step 2b:
Get some practice playing against real human opponents:
-> A sparring partner like Jimmy is a great option, so you can drill your lines and have him follow along your course lines, and then see how it feels once you're on your own. Most likely you'll have to do the same for Jimmy though. If you scratch his back, he'll scratch yours.
-> Failing that, playing in a Lichess pool for example (or anywhere your games are saved and so gathering the critical first mistakes from each game is easy), will show you how people actually play in the lines you're learning.

Step 3:
Review your first mistakes after you leave your opening, from step 2a and 2b.
-> Take a look at the engine analysis and think through the variations.
-> Make your own notes on what you missed, why you think you made the mistake, etc.
-> Triage your mistakes: Blunder? Don't need to revisit it, just stop blundering. Less obvious tactic? Make a flashcard to revisit it. Positional mistake / don't understand engine analysis? Move to step 4.

Step 4:
Now comes the moment you've all been waiting for when you clicked my clickbait title:
-> Have the coach explain the mistake.
-> Either live over a call, or it could be done asynchronously, written, audio, or video.
-> Attach the explanation to the flashcard.
-> Revisit it at optimal intervals using spaced repetition to ensure that you don't forget the idea, and that you never make the same mistake!

Summary:
There you have it:

- High ROI chess coaching, synchronous (live) or asynchronous.
- Frictionless connecting with a coach or student, without cancellations or rescheduling.
- On demand feedback on your mistakes instead of waiting for the next lesson.
- Revisiting the feedback with reviews at optimal intervals through flashcards.
- One key takeaway from all the blitz & rapid games you plan online.
... and playing early middlegames with confidence once you leave theory and you're on your own.

P.s. We make this whole end to end process frictionless for you on ChessFlow.org. Our first coach is IM Lawrence Trent and we're currently open for coach applications.

Anyways, I'll be the guy in the corner at the party staring at the ceiling if you have any questions. Now go play chess and go make some mistakes!

Calculation puzzle, solution:
1. Rf6+ Kb5 2. Rb7+ Ka5 3. b4+! cxb4 (3...Ka4 4. Ra6#) 4. Nb3+ Ka4 5. Ra6#