The Chess Cookie Jar

When you sit down for an important game, what does your brain remind you of? If you’re like most chess players, it helpfully replays that time you hung a piece in a winning position. Or when you lost on time with mate in two. Or that embarrassing loss to someone 300 points lower rated.

Thanks, brain. Very helpful.

Here’s the problem. We remember our blunders in high definition and our brilliancies in low resolution. One missed tactic can live rent-free in your head for weeks, while a clean positional squeeze against a stronger opponent gets forgotten by the next round.

That bias quickly destroys our confidence.

The solution is not fake positivity or telling yourself you are better than you are. That never works. What does work is evidence-based self-trust. This is where the “Chess Cookie Jar” comes in.

What the Chess Cookie Jar Actually Is

The concept comes from David Goggins, the ultramarathon runner and former Navy SEAL known for pushing through impossible challenges. His idea is simple: keep a record of your toughest moments and greatest victories. When adversity hits, you reach into that jar and remind yourself what you’re capable of.

For chess players, this translates beautifully.

Your Chess Cookie Jar is a personal archive of breakthrough moments. Not your entire game history. Just a curated collection of moments that demonstrate competence, growth, and resilience.

This includes games where you beat higher-rated players. Positions where you found a strong tactical or positional idea. Endgames you converted despite time trouble or complexity. Tournaments where you exceeded your rating expectations. Moments where you stayed composed instead of collapsing.

These are not random highlights. They are proof.

When confidence dips, you do not argue with emotions. You present evidence.

Why This Works in Chess

Chess players are brutally self-critical. That can be an advantage for improvement, but it becomes a liability before competition. Negativity bias hits chess players particularly hard because the game provides such clear, undeniable feedback. When you blunder a piece, there’s no ambiguity. You made a mistake, you lost material, and the position collapsed. That moment burns itself into your memory.

Meanwhile, your good moves often feel invisible. A well-timed prophylactic move that prevented your opponent’s idea never gets celebrated because the threat never materialized. A solid positional squeeze that led to a resignation can feel like your opponent simply played poorly rather than you playing well. The brilliancy that won you the game fades from memory within days, but that one missed tactic from three months ago still makes you wince.

This creates a distorted mental record. Your brain focuses more on failures and less on successes, so when you sit down for an important game, your internal narrative skews negative. You remember the times you cracked under pressure more vividly than the times you held firm. You recall the upsets you suffered more easily than the upsets you caused.

The practical effect is that your subjective sense of your own ability drifts below your actual level. You might be a 1600 player who has beaten 1800s multiple times, but when you sit across from an 1800, your brain whispers that you don’t belong there. It conveniently forgets the evidence that says otherwise.

The Chess Cookie Jar works because it forces you to store that evidence somewhere you can actually find it when doubt shows up.

You are not trying to convince yourself you will win. You are reminding yourself that you have handled similar situations before. That you have calculated under pressure. That you have defended worse positions. That you have earned your rating.

Confidence is not blind optimism. It comes from knowing you have handled hard things before and can handle them again.

How to Build Your Chess Cookie Jar

Start small and be selective. Quality matters more than quantity.

Create a dedicated folder, digital or physical. I recommend a ChessBase database or lichess study. Inside that area, store annotated PGN files of your best games with practical annotations. Screenshots of critical positions with a short note on what you found and why it mattered. Rating graphs showing upward trends or recovery after slumps. Tournament crosstables from events where you outperformed expectations.

Part of my personal cookie jar in a ChessBase database

A screenshot of my best tournament performance (so far)

A nice calculation sequence I did: 1. Rxd7! Qxd7 2. Nf6+! gxf6 3. exf6 Qd3 4. Be4!! 1-0

Add brief context to each item. One or two sentences is enough. What was the situation? Why did this moment matter? What does it proves about you as a player?

If it does not reinforce competence, resilience, or growth, it does not belong in the jar.

Pairing Analysis with Cookie Collection

The Chess Cookie Jar isn't a replacement for rigorous game analysis. It's the other half of the equation.

When you analyze games with engines, coaches, or tools like Chessalyz.ai that help you understand the thought patterns behind your mistakes, you're doing essential work. But here's the habit most players skip: after every analysis session, identify at least one thing you did well in that same game and add it to your Cookie Jar.

Maybe it's strong calculation right before your blunder. Maybe it's a defensive resource you found. These moments exist in every game, but we miss them while focusing on errors.

Make it a rule: one analysis session, one cookie added.

Your analysis database shows where to improve. Your Cookie Jar reminds you what you're capable of.

How to Use It Properly

The Chess Cookie Jar is not something you scroll through daily. Use it strategically.

Before a high-stakes game, spend three to five minutes reviewing two or three entries. Not analyzing them deeply. Just reminding yourself they exist. That you did those things. That the person who found that brilliant move is the same person about to sit down at the board.

When you see a scary pairing, recall the time you beat someone similar. After a bad loss, revisit your proof that the loss does not define your level. During a slump, remind yourself that progress is not linear.

This is strategic preparation, not self-soothing. You are calibrating your mindset to reality with evidence.

Build Your Own Mini Cookie Jar Today

Ask yourself these questions and write the answers down:

• What is one game I am genuinely proud of and why?
• What position do I remember solving correctly under pressure?
• When did I keep fighting instead of mentally resigning?
• What result surprised me in a positive way?
• What improvement over the past year is objectively measurable?

That alone puts you ahead of most players. The jar grows one cookie at a time.

If you want to take it further, I’ve built a complete fillable Chess Cookie Jar Template to help you build your own Chess Cookie Jar systematically.

Paid Substack subscribers can download the template below.

Final Thought

Strong players prepare openings. Serious players prepare their mindset.

The Chess Cookie Jar does not replace calculation, study, or endgame work. It supports them. When pressure hits, skill matters more when confidence is present.

You already have more proof than you think. You just need to store it where you can find it. Start building your jar today, and the next time doubt shows up, you’ll have the evidence.

I’ve created a fillable PDF template to help you build your own Chess Cookie Jar systematically. It includes structured sections for every type of confidence-building moment, space for PGN notation, and a quick-reference page for your top five moments to review before important games. Print it or fill it out digitally.

If you want to download the Chess Cookie Jar Template, go to the bottom of the page here: https://chesschatter.substack.com/p/the-chess-cookie-jar and become a paid subscriber to my "Chess Chatter" substack newsletter.

Paid subscribers also get access to all the digital downloads in the posts listed here: https://chesschatter.substack.com/t/paid-resources