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Meeting a chess master - and 7 lessons chess can teach us ♟
Meeting a chess master - and 7 lessons chess can teach us ♟

It was a Friday morning like any other... Well, except for the 16 chessboards lined up and ready for battle in the cafeteria.

Alex avatar
Written by Alex
Updated over 6 months ago

It was a Friday morning like any other... Well, except for the 16 chessboards lined up and ready for battle in the cafeteria. The tables were arranged in a horseshoe configuration, ready to be navigated by a chess master. Members of the different departments at Syft were gearing up for a Queen's Gambit-style match – 16 of us vs. the reigning South African chess champion, Daniel Cawdery.

Given my lengthy experience of playing chess – a single term on the chess team when I was twelve years old – I naturally suggested I join ranks with some of Syft's best chess players. The player seated next to me, Syft's Employee #1, David Golach, is a spectacular chess player who came closest to beating Cawdery, until a final fatal stumbling block. I, on the other hand, played Cawdery twice and was defeated twice.

But this wasn't merely a spectacle of mind-boggling chess. This was part of a series of Syft Talks in which fascinating professionals of all sorts come to talk to our team and inspire us to think about work and life a little differently. Previous iterations of these talks have prompted us to consider the business lessons to be learnt from rugby and how the future of AI looks surprisingly human. And, as many have said before me, there's a lot to be learned from chess.

Meeting a Champion

On 13 August 2022, we hosted Daniel Cawdery, the #1 rated chess player in South Africa, at the Syft office in Johannesburg. Cawdery is an International Master and 11 times national champion with a rating of 2412. He was also the winner of the last South African national open.

After Cawdery had beaten all 16 of us, we asked him what the best way to improve our chess skills would be. His response was to go for quality over quantity. Cawdery encouraged us to make the most of applications like Chess.com and stressed that playing a lot of games doesn't help you if you don't know the fundamental basics of the game.

First, you must master the basics – the quality – and then you can play. The greatest chess players may be geniuses, but they also dedicate a great deal of time to working on the game.

In some ways, modern technology makes chess too easy, Cawdery says. Today's young people don't have to spend hours reading books to improve their chess strategy like the older chess champions used to. With everything at your fingertips, it can be easy to neglect practice and theory. Nevertheless, it's important to remember that to do well in chess, you need to be able to recognize patterns. Chess puzzles are helpful as these force you to zero in on the ways in which you can solve specific problems.

The bottom line is this: being good at chess requires a lot of theoretical knowledge.

There are a lot of lines to know and a lot of openings. Many players go so far as to memorize openings. However, there are somewhere around 10,000 variations of openings, just at a basic level. So, memorizing them perfectly is a challenge, to say the least.

The end-game strategy is also very important. Cawdery says that in Europe, players focus on the end game first, then the mid-game, and then the beginning, whereas in South Africa, we tend to do the reverse. Whichever way you look at it, remembering patterns and strategies is crucial to playing a successful game of chess.

Is chess ability irrelevant in the age of the computer?

In 1996, the computer, Deep Blue, made history when it beat chess grandmaster, Garry Kasparov, at chess. As Kasparov says:

"The result was met with astonishment and grief by those who took it as a symbol of mankind’s submission before the almighty computer."

This was a critical moment in the history of computing, but it didn't signal the end of chess. Nowadays, computers regularly beat humans at chess, but people still tend to prefer human opponents.

Cawdery notes that there are certain uniquely human behaviors that computers simply don't comprehend. For instance, computers don't understand "compensation" as a concept. Compensation refers to the positional advantages one side may achieve in exchange for sacrificing pieces. This kind of sacrifice is difficult for a computer to fully understand.

Computers are great tools to train players, but chess isn't just about winning the match. The ultimate goal for chess masters is to have an objectively perfect game – something I don't think anyone would claim that a computer has had (or a person for that matter).

Good chess takes time

There's a reason I'm not so good at chess and it's not just that I'm not a genius. Sure, being a genius would help, but even geniuses need to put in the time. Alas, one term on the primary school chess team certainly doesn't count as doing the time...

According to Cawdery, the top chess players are homeschooled so that they have the time to dedicate to chess. Chess requires a lot of strategic thinking, a good understanding of the big picture, and intense concentration.

This reminds me of the 10,000 hour rule, which was popularized by Malcolm Gladwell in his bestselling book, Outliers. In a nutshell, the 10,000 rule means that it takes 10,000 hours of intensive practice to achieve mastery of complex skills and materials – like chess.

Cawdery says it's never too late to start playing chess – unless you want to remain competitive. Inevitably, your memory worsens as you age and having a good memory is critical to being successful at competitive chess. Starting at a younger age also means you have more time to perfect these skills.

When we asked Cawdery if there were any lessons we could take from chess and apply to lives, he kept it short: chess is life – or at least, chess imitates life. In an interesting reversal, Garry Kasparov famously wrote that life imitates chess. Let's unpack what we can learn about life and work from chess. This got me thinking about the ways in which we can apply chess logic to life. Here are seven elements of chess mastery that can be applied to other elements of our everyday lives.

1. Pattern recognition and problem-solving

To be truly skilled at chess, you need to be good at recognizing patterns and common problems and remembering how to find the right solutions to these problems. The same can be said of life. When we are young and less experienced, we are more likely to stumble into situations or relationships that do not suit us or are ill-advised, but, as we grow through these experiences, we learn to avoid certain things and steer towards others in future.

2. Not jumping to conclusions

Chess also teaches us not to make assumptions about outcomes based on limited pieces of information – like the pieces right in front of us – but to consider other possibilities. As the renowned filmmaker Stanley Kubrick puts it:

“Among a great many other things that chess teaches you is to control the initial excitement you feel when you see something that looks good. It trains you to think before grabbing and to think just as objectively when you’re in trouble.”

Whether it looks like you're very clearly going to take your opponent's knight or lose your queen, sometimes, it's best to pause and consider whether this really is inevitable, whether it's worth it, whether there's something you might be missing.

When it comes to business, this may mean looking at a number of different KPIs in your business to determine how well business is going and to plan for the future, rather than just focusing on profit, for instance.

3. Looking at the big picture

Oftentimes, you can become so focused on a single goal or issue that you miss out on the bigger picture. Say, for instance, that you are singularly focused on proving your worth so you can get a promotion at work. However, with all the time spent focusing on this goal, you may be missing out on time spent with your daughter who needs your support and attention too. If you maintain such a narrow perspective of what's important, you begin to neglect other equally – or even more important – areas of your life from your relationships to your physical and mental health.

As Cawdery cautioned the Syft team: don't be too focused on one area of the board or on one move, otherwise you can miss a great opportunity.

It's good to look at your options, to see if there's an alternative route to achieving your goal or an alternative way to spend your time. As French-Polish chess grandmaster, Savielly Tartakower put it, “To avoid losing a piece, many a person has lost the game." In everyday life, we might say, "Pick your battles." Is it worth arguing over trifles with your family and ruining your Sunday evening or should you save your energy for the fights that really matter?

The greatest criticism of the Syft team's playing that the South African champion gave us was that we missed his threats. We were too busy thinking about our moves to consider his and we were too focused on one section of the board instead of the whole board.

4. Making a move

It's good to be strategic and think through your options, but nothing will happen if you don't make a move. At a certain point in time, you need to stop theorizing and take action.

Making a move in chess can be daunting, especially if you think it could be risky. But not making a move is worse. As Kasparov says, “If you wish to succeed you must brave the risk of failure.” The same is true of life. Asking someone out on a date can be terrifying and no matter how many hours you spend thinking of the perfect way to ask, it will probably still be terrifying, but if you never ask, you'll never know if you would've been successful or not.

Writers are encouraged to take a similar approach – you may as well write something, even if it's terrible, than have a blank page. Terrible words can be edited and reworked, but a blank page is still a blank page.

5. Dealing with mistakes

Even very skilled chess players sometimes make mistakes. It's only human. However, it's not our mistakes that define our ability, and, as German chess player and previous World Chess Champion, Emmanuel Lasker, once said, “Without error there can be no brilliancy.” You can only properly recognize moments of brilliance if you have stumbling blocks to compare them to. And if you don't make mistakes along the way – in life as in chess – you are missing out on a huge opportunity.

6. Making sacrifices

You have to lose battles to win the war. Sometimes you need to take a gambit – sacrifice a piece to gain an advantage. In chess, we learn to sacrifice a valuable piece for long-term success. Sometimes you need to give up your Queen – the most valuable piece you – in order to checkmate your opponent in a few moves' time.

Similarly, there are occasions in life where you will be required to make compromises. This may mean sacrificing time that you would usually spend playing games to study – a short-term sacrifice for a long-term goal you'd like to achieve. Or perhaps it means giving up your easy commute to work in exchange for an easier commute to far-flung loved ones.

Sometimes, short-term satisfaction must be sacrificed for long-term outcomes to be reached. This is a tough lesson for 21st-century dwellers who are so accustomed to instant gratification, but it's worth remembering that when the sacrifices we make pay off, they make it all worthwhile.

7. Being pliable

Not everything is smooth sailing, even if you have a strategy mapped out. Sometimes, your opponent will respond differently from how you expected and you will be required to rethink your game.

As American chess grandmaster, Bobby Fischer, put it, “Chess is a matter of delicate judgment, knowing when to punch and how to duck.” You have to be measured in your responses, but also able to change your tactics when the game changes.

Being adaptable is perhaps one of the most crucial skills in the world of work today – as we noticed during the pandemic. And when we live in an environment that is dominated by ever-changing technology, remaining open to change is vital.

What happens after checkmate?

The world of chess can teach us a great deal about life. However, there is, a crucial difference between the two. As renowned science fiction writer, Isaac Asimov, put it, "In life, unlike chess, the game continues after checkmate." This can be interpreted in a number of ways. For one, after one person dies in real life, the world still keeps spinning. Life goes on.

Another way we could read this is that even if you lose somehow in the game of life – perhaps your marriage fails, you get fired, or your business goes bust – your life will not suddenly come to a halt.

In life, our checkmates are rarely fatal.

You can still go on after divorce, after losing your job, after your business closes. It's a matter of rebuilding, reworking, starting over again – and trying a different approach. If you've used your chess brain to analyze the patterns in your life, you can work to avoid the ones that didn't work last time and strategize for a better outcome in future relationships, jobs, businesses, and so on. Human beings are remarkably resilient creatures.

The South African national champion may have defeated us in chess this time, but there's always another game around the corner – certainly in the Syft office. And even if my chess skills reflect the lack of time I've dedicated to the craft, at least I can say that I tried – I made the move. The blank page now has writing on it. We've gone from zero to one.

What do you think? What has chess taught you about life, business, or the world?


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