A Losing Match

I recently hit a 650-day streak on Duolingo, and I’m very proud of myself. I first started using the app to improve my English, then dabbled in Spanish and Cantonese. More recently, I’ve been spending my time learning chess.

It was a lot of fun. I still remember that it was the Netflix series The Queen’s Gambit that first sparked my interest in the game. I’m not very good at it yet. Pawns, rooks, bishops, knights, queen, and king — something is fascinating about the simplicity of the board and the pieces, contrasted with the sophistication of the strategies and movements. Chess is elegant in its design, yet incredibly complex in execution. It has long been associated with intelligence, especially when played well.

As we all know, every game has a winner and a loser. But when I paint a chessboard depicting an endgame position, what do you see yourself as? The winner or the loser?

Most people would probably say, “The winner, of course.” Or at least they would want to. After all, who enjoys losing?

That’s why the game I am depicting here is shown from the winner’s perspective. If you look closely, you can tell that Black has already checkmated White.

But I am the White player.

So, I am the loser.

Being a loser sucks. Yet losing is often how we learn.

People love reading stories about successful entrepreneurs — how they survived fierce competition, overcame impossible odds, and persevered through adversity. But has anyone stopped to wonder whether the people who failed faced the same circumstances? Why didn’t they make it?

Perhaps failure carries a shame that discourages people from talking about it openly. Yet it is those stories — the unsuccessful attempts, the overlooked mistakes, the painful lessons — that can teach us ten times more than success ever could. They reveal what we should pay attention to.

Because the truth is, you can be the smartest person in the room. You can cultivate courage, grit, and a strong presence. You can overcome countless obstacles. Yet a single mistake — one that even successful people may overlook — can still trip you up. Something as simple as poor organization in a demanding operational role can undermine years of hard work, especially in environments that celebrate sales and growth while overlooking the systems that support them.

I have always been more of an observer than a participant. I’m rarely the loudest person in the room, and I’m certainly not the one who wins all the time. But I know that given enough time and resources, I can find flaws in a system and correct them before anyone else notices.

So, am I still the loser?

No.

Winning and losing are temporary states. A losing match can teach you far more than a winning one ever will.

That is why this painting is shown from the winner’s perspective, yet it is called A Losing Match. Because if you remember your losing matches, one day you will find yourself standing where the winner once stood.

It’s all about perspective — and a little bit of hindsight.