The Book That Taught Me to Play My Own Game
Part I of The Checkmate Strategy traces twenty books that shaped the way I think. This is the third.
Chess for Tigers is not a famous book.
Written by Simon Webb and first published in 1978, it has never had the profile of the great chess classics. It is not Kasparov on strategy or Fischer on his games. It is a short, practical, occasionally irreverent guide to winning chess — not at the grandmaster level, but at the level most club players actually inhabit.
That is precisely what makes it interesting.
What Webb Argued
Webb's central premise is straightforward and quietly radical. Most chess players lose not because they play badly in an absolute sense, but because they play the wrong game. They aim for the theoretically perfect position rather than the practically winnable one. They try to produce brilliant moves rather than correct ones. They play to impress rather than to win.
His advice is equally straightforward. Know what kind of player you are. Know what kind of game you play well. And then play that game — against this opponent, in this position, on this day — rather than the game that would look most impressive to an observer.
Win the game you are actually in. Not the game that exists in theory.
Why This Is a More Demanding Idea Than It Appears
There is something uncomfortable about Webb's argument for anyone with competitive instincts.
It requires self-knowledge rather than self-improvement. It asks you to understand your limitations honestly and work within them rather than transcending them. It values the pragmatic over the brilliant. It suggests that the player who consistently wins modest victories from positions they understand is doing something more strategically sound than the player who occasionally produces brilliance from positions they do not.
This is not a popular idea in any competitive field. Most professional cultures celebrate the brilliant move, the audacious decision, the strategy that breaks the conventional mould. Webb is arguing for something quieter and more reliable — the discipline of playing your game rather than someone else's.
How It Connected to My Own Career
When I built my tax practice I did not try to compete with the large firms on their terms. I did not pursue the complex scheme work, the institutional clients, or the technical bravura that defined success in the profession's conventional terms.
I built a practice around fixed fees, ethical clarity and small businesses — clients who needed someone who understood their situation and communicated clearly, not someone who demonstrated the most impressive technical range. I played my game. Not the profession's default one.
At the time this felt like a pragmatic decision shaped by my circumstances. Reading Chess for Tigers helped me understand that it was actually a strategic one — and that the discipline of knowing which game to play is one of the most underrated competitive advantages available.
A solicitor who approached me about expanding into scheme-based work was offering me a different game. A more lucrative one, perhaps. But not mine. The refusal was not heroic. It was simply alignment — the same alignment Webb describes when a chess player declines a sharp tactical line that might produce brilliance but sits outside their natural style.
The Connection to The Win
The Checkmate Strategy describes The Win as the discipline of defining success honestly before pursuing it. Winning that is not defined deliberately will be defined by default — by whatever arrives fastest, rewards most visibly, or carries the most institutional approval.
Chess for Tigers is a book about exactly this. Webb's players fail not because they lack ability but because they pursue the wrong definition of winning — the theoretically impressive game rather than the practically effective one.
The question The Win asks is not whether you can win the game that would impress the most observers. It is whether you can name the game you are actually trying to win — and have the discipline to play that one instead.
The Question Worth Sitting With
Most professionals develop a default understanding of what success looks like in their field. The marks of achievement that the profession recognises, rewards and talks about.
Ask honestly: is that the game you are actually trying to win — or is it the game that has simply arrived by default?
If the answer is the latter, the first step is not to work harder at the existing game. It is to decide which game you are actually playing — and whether that definition of winning is yours or someone else's.
That is Chess for Tigers applied to professional life. And it is one of the most useful questions in The Checkmate Strategy.
The Checkmate Strategy is available on Amazon. If you are finding these posts useful, subscribe below to receive one each week — drawn from the twenty books and forty-two lessons that shaped the framework.
Next week: The Hobbit — and what Tolkien taught me about the role of wonder in strategic thinking.
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