Playing to Win
A friend and I were catching up the other day, and, as always, our conversation got a little philosophical. We started talking about how, no matter what your goals, dreams, or ambitions are, there’s always some kind of “game” you have to play to get ahead.
Think about politics: if you want to climb the greasy pole, you might feel pressured to lie, cheat, or even backstab along the way.
My friend made a cliché but necessary point: you can always choose not to play the game and just be yourself. True, no one’s holding a gun to your head, but those who refuse to play usually end up unsuccessful in the conventional sense, at least.
The Quitter: Jeremy Corbyn
Take Jeremy Corbyn. He’s a man of integrity who’s always championed the underdog. Yet despite his passion, he never convinced enough people to vote him in as Prime Minister.
Sure, the right-wing media ran a relentless smear campaign, but honestly, Corbyn’s downfall runs deeper: he simply wasn’t cut out for the ruthless, back-room maneuvering that modern politics demands.
He had too much integrity to play the Machiavellian game—and so, in conventional terms, he lost. In the end, his refusal to compromise relegated him to the role of protester, stripped of any real power to change the things he cared about most.
The Player: Keir Starmer
Contrast that with Keir Starmer, who seems to have mastered the art of the political game. Once a firebrand who even wrote a piece arguing for abolishing the monarchy, Starmer has since quietly shelved many of his earlier convictions.
His critics say, “What does he actually believe in?” The truth is, he does have beliefs—but he loves acquiring and retaining power even more. He understands that politics is a dirty business with no room for rigid personal convictions.
He’s not just playing to win; he’s playing to keep winning. And if you ask me, that’s both impressive and a little unsettling.
The Natural: Tony Blair
Then there’s the third category: those rare figures who can be themselves and still win the game. Tony Blair is the poster child here. He didn’t just win—he crushed it, securing two of the largest Labour majorities in UK history and becoming the only Labour PM to serve more than one term.
Blair was naturally charismatic, intuitively Machiavellian, and—crucially—his views matched the zeitgeist of the ’90s. He played the game masterfully, without ever looking like he was playing.
What About Us?
Of course, politics is just one arena. In the corporate world, smarts and hard work alone rarely guarantee success, especially if you’re from a minority background or lower socio-economic status.
To make it to the top, you’ve got to look the part, network relentlessly, and cultivate likability. If you decided to be authentically you, at best, it lands you a middle-management role with no clear path up.
So, we’ve got the principled non-player who loses (Corbyn), the ruthless player who wins (Starmer), and the lucky natural who wins by being himself (Blair). Clearly, Blair hit the lottery. But most of us aren’t born with that perfect blend of talent, timing, and opportunity.
If you’re like me, you might wonder: should I stick to my principles and accept “failure,” or do I grit my teeth and learn the rules of the game?
Right now, my ego is too big to settle for conventional definitions of failure. I’m still figuring out how far I’m willing to compromise my values for power—or whether there are lines I’ll never cross.
One thing I know for sure: there are certain moral principles I could never trade, no matter how badly I want to win.