My classmate taught me how to play chess during my secondary school days.

Remember those wonderful weeks after the school exams where our teachers leave us to “study” on our  own?

As a newbie, I was very surprised to be checkmated in 4 bloody short moves!? Huh? 

I was “taught” how each chess pieces move; but was not taught “how” to play chess.

I learned from my mistakes and now I am puzzled how my classmates were able to counteract my early opening moves without much thinking on their part.

That is until I realised that they have memorised the popular chess opening moves. No wonder! 

I too started reading chess books.

And learned the classic chess openings like Ruy Lopez, French Defense, Queen’s Gambit, etc.

Now some of my classmates don’t seem so smart now. I started to win more games.

What comes next is the exciting middle game of chess. Rote learning does not help here. Strategies and tactics matter more.

The more chess games I played, the better I become. 

I realise its because I got better at recognising the patterns of the chess pieces and it’s relation to the spatial positioning on the chessboard.

When to sacrifice material for positioning advantage; and when to give up positioning advantage to win back the initiative… Books can’t teach you all these. We have to learn it through trial and error. Or practice, practice, practice!

Some of the best learning came from defeats by better opponents. I can “borrow with pride” their winning strategies or tactics that were used on me in my next game ;)

Soon, I’ve reached my bottle-neck in chess playing. The end game is where the boys (me) are separated from the men.

Mediocrity is hard to conceal when there’s simplicity. An empty chessboard with only a few remaining chess pieces. You either know or don’t know. Period. 

You got to think and make your own decisions. You’re on your own! 

And now you have your answer to the debate between nature versus nurture…

Non chess players do not fret. Just substitute chess playing to another game or sport that you love playing passionately – just like in investing or trading.

I think golf is another great analogy to chess playing :)

Fellow investors and traders, can you relate to the chess analogy above? 

It’s humbling to know that after so many years in the markets, we sometimes fuxx up the end game don’t we?


Some externalise and blame. 

Some internalise and reflect. 

Not everyone can be great investors and traders. Good is enough for me :)

Singapore Man of Leisure (welcome to my blog; just google it!)