Olivia: Most of what we're taught about winning is wrong. In fact, in the most important games of life and business, trying to 'win' is a guaranteed way to lose. We're about to explain why. Jackson: That is a bold claim, Olivia. It sounds like something designed to break my brain on a Monday morning. But I'm intrigued. Olivia: It’s the provocative idea at the heart of The Infinite Game by Simon Sinek. Jackson: Ah, Sinek. The 'Start with Why' guy. I know his TED talk is one of the most viewed of all time. What's interesting is that he's a trained cultural anthropologist, not a business school professor. He looks at organizations almost like a tribe, studying their behaviors and beliefs. Olivia: Exactly. And that perspective is key here. He even delayed this book's publication because he refused to rush it for a deadline he felt was arbitrary. He said he wanted the book itself to be built to last, which is, ironically, the entire point of the book. Jackson: Okay, so this idea of 'winning is losing'... that sounds like a riddle. Where do we even start with that?

Olivia: We start with a historical paradox that Sinek uses to frame the whole book: the Vietnam War. By almost every traditional metric, the United States was winning. They had more resources, superior technology, and in most direct battles, they inflicted far heavier casualties. The Tết Offensive in 1968, for example, was a crushing military defeat for North Vietnam. Jackson: Right, I remember learning about that. The US forces repelled every single attack. So how on earth did they end up losing the war? It doesn't make sense. Olivia: It doesn't make sense if you think there was only one game being played. Sinek argues that the United States was playing a finite game, while the North Vietnamese were playing an infinite game. Jackson: Hold on. Finite vs. Infinite. You've got to break that down for me. Olivia: Of course. A finite game has known players, fixed rules, and a clear, agreed-upon objective. When that objective is met, the game ends, and someone is declared the winner. Think of a football game. There's a clock, a scoreboard, and when time runs out, we know who won. Jackson: Okay, simple enough. A finite game is a contest with an end. So what's an infinite game? Olivia: An infinite game has both known and unknown players. The rules are changeable, and there is no finish line. The objective is not to win, but to perpetuate the game—to keep playing. Jackson: That’s a bit more abstract. So a finite game is like a football match, but an infinite game is like... marriage? Or friendship? There's no "winning" marriage. The goal is to stay in it, to keep it healthy and growing. Olivia: That's a perfect analogy. And Sinek's big argument is that business, politics, and life itself are all infinite games. The problem is, too many leaders play them with a finite mindset. They're trying to "win" a game that has no end. Jackson: And that's where the Vietnam paradox comes in. The US was playing to win battles and achieve a political objective—a finite goal. But the North Vietnamese were playing for their survival, for their independence. They were willing to fight for a thousand years. Their game had no end. Olivia: Precisely. The US exhausted its resources and, more importantly, its will to play. They dropped out of the game. The North Vietnamese, playing an infinite game, simply outlasted them. Jackson: Wow. Okay, that clicks. Can you give me a business example? This feels like it could get very real for companies. Olivia: Absolutely. Think of Microsoft in the mid-2000s. Apple had the iPod, and it was dominating the market. Microsoft, with its massive resources, decided to enter the game. They launched the Zune. Jackson: Oh, the Zune! I remember the Zune. It was actually a pretty good device, technically. Olivia: It was! But listen to how Microsoft talked about it. Their executives were obsessed with "beating Apple" and "stealing market share." They were playing a finite game: win the MP3 player market. Meanwhile, Apple wasn't focused on beating Microsoft. They were focused on their own infinite game, their Just Cause: helping people enjoy music and empowering creativity. They were so unconcerned that when an Apple executive was told the Zune was technically better, he just shrugged and said, "I have no doubt." Jackson: And we all know how that ended. Apple went on to create the iPhone, which made the entire category of MP3 players obsolete. Microsoft was so focused on winning the battle with the Zune that they didn't even see the real game Apple was playing. Olivia: Exactly. Microsoft exhausted its will and resources on the Zune and eventually discontinued it. They "lost" because they were playing to win, while Apple was playing to advance their cause, forever. Jackson: This is a great story, but I have to bring up a common critique of Sinek's work. Some reviewers say he oversimplifies these cases or cherry-picks examples to fit his narrative. Was Microsoft really that clueless, or is this just a convenient story? Olivia: That's a fair point, and it's a criticism that follows a lot of big-idea business books. Of course, the reality inside Microsoft was more complex. But Sinek isn't trying to write a detailed business history. He's providing a framework, a lens. And when you look through that lens of finite vs. infinite mindsets, the patterns of behavior at Microsoft versus Apple become incredibly clear and instructive. It reveals the danger of focusing on the competition instead of your own vision.

Jackson: Okay, so if the goal in business is just to keep playing, how do you stay motivated? What's the point? It sounds kind of... aimless and exhausting. Olivia: That's the million-dollar question, and Sinek has a powerful answer. You can't play an infinite game without a "Just Cause." This is the first and most important practice for an infinite-minded leader. Jackson: A Just Cause. How is that different from a standard corporate mission statement, like "To be the best" or "To maximize shareholder value"? Olivia: They're worlds apart. A Just Cause isn't about you; it's about a future state so appealing that people are willing to make sacrifices to help build it. It's a vision of a world that doesn't exist yet. To really understand it, I have to tell you one of the most incredible stories in the book. It's about the Leningrad Seed Bank during World War II. Jackson: I'm listening. Olivia: During the nearly 900-day Nazi siege of Leningrad, over a million citizens died, mostly from starvation. People were eating wallpaper paste, leather, anything they could find. It was hell on earth. But hidden in the city was one of the world's largest collections of seeds and plant life, created by a botanist named Nikolai Vavilov. His Just Cause was to end hunger on a global scale by preserving genetic diversity. Jackson: So he had a vault full of potential food in the middle of a starving city. That's a tense setup. Olivia: Incredibly tense. Vavilov himself was imprisoned by Stalin, but his team of scientists stayed behind to protect the seed bank. They guarded it from rats, from bombs, and from the starving populace. And here's the most unbelievable part: while the city starved, nine of those scientists died of starvation inside the seed bank, surrounded by tons of edible rice, corn, and potatoes. Jackson: Wait, what? They starved to death rather than eat the seeds they were protecting? Olivia: Yes. One of the survivors, Vadim Lekhnovich, was asked later how they could possibly do that. He said, "it was not in the least difficult to refrain from eating... For what was involved was the cause of your life, the cause of your comrades’ lives." They weren't protecting seeds; they were protecting the future of humanity. They were willing to die so that their Just Cause could live on. Jackson: That's... an absolutely insane level of commitment. It gives me chills. That story makes any corporate mission statement sound like a joke. So that's a Just Cause. Olivia: That's a Just Cause. It has to be for something positive, not just against something. It must be inclusive, open to anyone who wants to contribute. It has to be service-oriented, for the primary benefit of others. It must be resilient, able to endure change. And finally, it has to be idealistic—ultimately unachievable. Jackson: Unachievable? Why? Olivia: Because if you can achieve it, the game is over. The Declaration of Independence says "all men are created equal." That's a Just Cause. We've been working on it for over 240 years, and we'll never perfectly achieve it. But the pursuit of that ideal is what keeps the American experiment moving forward. That's the engine of an infinite game.

Olivia: And that's the key—a Just Cause is about advancing a vision, not beating someone. But that doesn't mean other players aren't important. In fact, they can be your greatest asset, if you reframe them not as competitors, but as "Worthy Rivals." Jackson: A Worthy Rival. I like the sound of that. It sounds more noble than just 'the competition.' Olivia: It is. And Sinek introduces this idea with a very personal and vulnerable story. He admits that for years, he had a professional rival, the author Adam Grant. He says whenever he heard Grant's name, he'd get uncomfortable. He'd obsessively check their book rankings on Amazon. If his was higher, he felt a rush of superiority. If Grant's was higher, it would ruin his day. Jackson: Oh, I know that feeling. We've all had that professional rival where their success just gets under your skin. It's such a human, and frankly, not very flattering, emotion. Olivia: Totally. And Sinek was stuck in this finite game of "beating Adam Grant." Then, one day, they were invited to share a stage for an interview. The interviewer asked them to introduce each other. Sinek went first and decided to be completely honest. He turned to Grant and said, and I'm quoting here, "You make me unbelievably insecure because all of your strengths are all my weaknesses." Jackson: Wow. To say that out loud, on a stage, to the person you feel competitive with... that takes guts. What did Grant say? Olivia: Grant smiled and replied, "The insecurity is mutual." It turned out Grant felt the same way about Sinek's strengths. In that moment, Sinek realized his obsession wasn't about Adam Grant at all. It was about his own weaknesses. Grant was simply the mirror showing him where he needed to improve. He wasn't a competitor to be beaten; he was a Worthy Rival who could make him better. Jackson: So how does that jealousy turn into something productive? It’s one thing to recognize it, another to use it. Olivia: You use them as a benchmark. You study what they do well and let it inspire you to improve your own game. The classic example Sinek uses is Apple and IBM in the early 80s. When IBM, the Goliath of the corporate world, entered the personal computer market, everyone expected Apple to panic. Jackson: Right, because IBM was "Big Blue." The safe, corporate choice. "No one ever got fired for buying IBM," as the saying went. Olivia: Exactly. But Apple didn't panic. They took out a full-page ad in The Wall Street Journal with a simple headline: "Welcome, IBM. Seriously." They didn't see IBM as a competitor to be destroyed; they saw them as a Worthy Rival. IBM represented the establishment, the status quo. Apple used IBM as a foil to clarify their own Just Cause: to be the pirates, the rebels, the tool for individuals to challenge the system. IBM helped Apple define who they were by showing the world who they were not.

Jackson: So it seems like it all comes back to a fundamental choice. Are you playing to win a quarter, or are you building something that will outlast you? It's not just a business strategy; it's a philosophy for how you engage with the world. You're either playing to beat the person next to you, or you're playing to advance a vision on the horizon. Olivia: Exactly. And the paradox is that when you stop trying to 'win' and start playing for a Just Cause, you often end up with better results anyway. Look at CVS. In 2014, they decided to stop selling tobacco products because it conflicted with their Just Cause of "Helping people on their path to better health." Jackson: I remember that. Wall Street must have hated it. That was a huge revenue stream. Olivia: They did. Analysts predicted disaster. The company lost an estimated $2 billion in annual revenue. Their stock dipped... for a day. But the public support was overwhelming. Other health-focused companies signed on to be sold in their stores. And within a year and a half, CVS's stock price had doubled. Why? Because they proved their Just Cause was real, and that built an incredible amount of trust with customers, employees, and partners. They chose the infinite game, and it paid off in every sense of the word. Jackson: That's incredible. It really makes you wonder, in our own lives—our careers, our relationships—what game are we actually playing? And are we playing it to win, or playing it to last? Olivia: This is Aibrary, signing off.