Top 5 Mistakes in Chess: #1 Building a Redwood

Whether you’re brand new to chess or have played many tournaments, improving often comes down to fixing the simple, avoidable mistakes we all make—but don’t always recognize. Over the years as a coach and player, I’ve seen certain habits pop up again and again, no matter a player’s age or experience level. 

In this series, we’ll break down the Top 5 Chess Mistakes that hold players back, and more importantly, how to fix them. If you’ve ever felt stuck in your progress, one of these could be the reason why.

1. Building a Redwood

I recently asked a student to work through the basic chess thinking model (Candidates --> Calculation --> Evaluation) in this position. They identified correct candidate moves in Ne4, Nb5, and Bb5. Then they proceeded to calculate the following variation:

From a distance, this seems to be pretty solid calculation. They looked at very forcing critical moves and saw what kind of positions that would lead them to. The issue with their calculation is that they are building a redwood. 

Calculation in chess is often referred to as a tree, as introduced by Kotov in "Think Like a Grandmaster". Each variation or deviation creates a new branch for your tree. When people are calculating, the issue I see a lot is that instead of making a tree or even what I call a shrub (a lot of smaller variations). People spend oodles of time on one variation. This method of calculation will inevitably fail because a) you are neglecting a host of other options and branches, and b) you are human and bound to miscalculate something the longer the variation goes.

Richard Réti was once asked how far ahead he had to calculate in a tournament. He quipped, “Only two moves!” He was likely exaggerating, but there is some serious truth to that. Calculating a variation should rarely be lengthy, what makes calculating time-consuming is the quantity of variations/branches, not the depth of them. Looking back to the example, my student's redwood did not hold up to further analysis.

I am absolutely victim to this mistake, as is almost every chess player. Here is an example from a recent classical tournament I played against none other than GM Awonder Liang (2700 FIDE, 33rd in the world). I ended up spending roughly 20 minutes in the position below (I was black, he was white) calculating all the complications because my gut was telling me that e5 was the right idea, I just had to make sure it worked. This is roughly what my calculation looked like (Black to move):

Granted, this position is quite complex and is worth spending a good chunk of time calculating. However, my fatal error was that a) I didn't look at 3-5 candidate moves, I just jumped straight into calculating my first instinct and b) I miscalculated in the mess of calculations following e5

Here is how the game transpired following this miscalculation:

It turns out, your gut can be wrong sometimes. The big problem was that because I hadn't even considered Bc5 and I already spent 20 minutes calculating e5, I was stuck in a fresh position I didn't understand and couldn't afford to go into the tank again to figure it out. So, as you saw, that one mistake or inaccuracy led to another and another. He outplayed me for another hour or so before I resigned. Building a redwood is scary! The tree can easily topple over and kill you(r chances of winning).

Let's look at a good calculation tree which is more tree or shrub-like might have looked like in that position:

Based on these new and improved calculations which are more balanced and shorter, take some time to use your evaluating and decision-making skills to figure out which move black should play.

Note: These are just my calculations (I didn't check with an engine). There could very well be errors in them, but they should suffice to get the correct answer. You may also notice that there are still some 4-5 move long variations, but only when there are very forcing variations with a lot of captures. Those variations are exceptions. 

The answer is ... Rc8! Everything else weakens black's position in some way. e5 weakens the d5 pawn, moving the knight can open up lines to e6 or h7. Rc8 is just a good improving move. There is no need to do anything crazy. As Awonder told me after the game, there is only one weakness in the position (e6) and generally if you only have one weakness, you can defend that weakness without too many issues. I spent 20 minutes calculating complicated variations, and the best move was the simplest of them all.

Overall, this same principle of looking at all your options before starting down a path is not just important in chess, but also in life. For example, when an engineer does a bad job on a project, it isn't usually because they are bad at engineering. It is often because they have a vision for the project, and they never stray from that vision. They fail to consider the other options or possibilities. In this way, chess is great for teaching problem-solving skills.

Everyone makes mistakes in chess and life—that’s how we learn. The key is to slow down, reflect/recognize patterns, and build habits that will lead to long-term improvement. So make sure that you are looking at more than one option every time you are about to make a move!

Stay tuned for the next post coming soon!

If you're looking for more chess guidance and a fun, growth-focused community to sharpen your game, check out Thunder Chess Academy.