Winner's Game vs. Loser's Game
29 Jan 2026 · 8 min
Sahil Bloom explains why some games reward brilliant moves while others reward avoiding mistakes. In tennis, amateurs lose by unforced errors; pros win through them. Alex Caruso became an NBA star by doing ordinary things consistently well, not by chasing highlight plays.
Questions this episode answers
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Hello and welcome to the Curiosity Chronicle, a weekly podcast where I provide actionable ideas to help you build a high performing, healthy, wealthy life. Today's podcast is brought to you by AG1 by Athletic Greens my all in one daily supplement. Seriously, this stuff replaced an entire cabinet of supplements for me in one Daily Scoop. There's a reason it's been a staple of my morning routine since 2011. To find out why, go to drinkag1.comsahil and and take advantage of a limited time offer. Now on to today's piece Winner's game versus Loser's Game A mental model is a way to think about the world. The aim of any good model is to provide a lens through which you can simplify, evaluate and make decisions as you walk through life. The most useful mental models are highly dynamic, meaning they can be leveraged in a variety of contexts and situations. While I've come across hundreds, maybe even thousands of mental models during my life, I occasionally find one that creates such clear, profound value that I feel compelled to share it with all of you. Today, I'd like to do just that and cover a powerful mental model with applications for business, investing, careers and life Winner's game versus Loser's game Know the game you're playing. When I arrived at Stanford on a baseball scholarship in 2009, I I assumed that in order to pitch effectively at that level, I would have to blow hitters away in every appearance. During my freshman fall, I strained, pressed, and grunted in an effort to put everything I had into each pitch, but the results were abysmal. In fact, it was the worst I had ever performed in my baseball career. I got behind in counts, walked batters, and gave up a whole lot of hits. It was brutal and discouraging. That all changed when an assistant coach pulled me aside and offered one piece of you're playing the wrong game. What he meant I had achieved success in my baseball career, including getting my scholarship, by consistently throwing strikes and making the hitters beat me. But upon arriving at school, I had tried to play a different game, trying to throw perfect pitches with maximum intensity to beat the hitters. Once I reverted to my old game, I was back on track. I never blew anyone away, but I had a successful college baseball career by forcing the action into their court. As it turns out, the experience had been a real world case Study in the importance of knowing the game you're playing in the 1999 tennis book extraordinary Tennis for the Ordinary Tennis Player, author Simon Ramo broke down the difference between amateur and professional tennis. Amateur tennis is a loser's game. 80% of points are lost on unforced errors. You win by avoiding errors and waiting for your opponent to make errors. Professional tennis is a winner's game. 80% of points are won on incredible shots. You win by hitting incredible shots. The core insight? You have to know what kind of game you're playing. There's no point trying to hit magnificent shots if you're playing a loser's game. You're better off keeping it simple and avoiding unforced errors. There's no point trying to play conservatively and avoid unforced errors. If you're playing a winner's game. You're better off trying to hit the elegant shots. I had incorrectly assumed that college baseball was a winner's game. I tried to make the incredible pitch, but it led to more unnecessary mistakes. My coach's reminder was a reset button. I started playing the loser's game and that made me a winner. Two Lessons to Apply to Life the Winner's Game vs. Losers Game Mental model is one that I come back to over and over again. There are two core lessons that you can apply to your life today. 1. Avoid the complexity trap here's an important truth. Most games in life are losers. Games. You don't get paid for complex, magnificent shots. You get paid for consistently avoiding unforced errors. For figuring it out. For showing up and doing what you say you're going to do. The sum of consistent, ordinary performances adds up to something extraordinary. But intelligent people are naturally drawn to sexy, complex answers and solutions. Why? Because they make you sound interesting. At a party, when someone asks about your latest investments, work projects or health habits, the most complex, interesting answer always seems to draw the most attention. If you say you like to buy and hold index funds, people quickly move on to the person who is running a crazy covered call. Crypto Arbitrage Hedge fund strategy. If you say you like to move your body and eat whole, unprocessed foods, people quickly move on to the person who is using red light therapy gene infusion to Benjamin Button themselves back into their teenage years. The point here is that sexy sells when you're in a social setting, so smart people are often sucked into it. They start trying to play a winner's game because it makes them sound more interesting. But the pull towards complexity is a trap. S1 mple usually wins in the long run. You don't need talent or luck to win a loser's game. You just need to keep showing up. 2. Embrace self awareness Alex Caruso entered the NBA's Development League after going undrafted in 2016. A few years later, he was a key player leading the Los Angeles Lakers to an NBA championship. When asked about how he rose from undrafted nobody to this level of stardom, he said that self awareness was the key A big reason guys get stuck in the development league is because they don't realize the position they're trying out for. It's like going to a job interview thinking you're going to be the CFO of the company and they're looking for someone to clean the bathrooms. It's a self awareness of understanding what you're good at, what teams need, and trying to do that. Caruso knew that he wasn't going to win if he tried to play the NBA superstar game. He wasn't talented enough for that, but he knew he could fill a specific role on a roster, play that role consistently and help a team win. He knew that ego was the enemy and self awareness was the friend. Success in any endeavor requires you to answer two questions. One what kind of game am I playing? And two. Is this a game I can win? If you can honestly answer yes to the second question, you're on the right path. If not, you need to find a different game. Life's a game. Every area of your life can be thought of as a game. Your relationships, your health, your career, your finances. In each case, the game is a long one, played over and over again until the end of your days. You have a choice of how to play. Occasionally, a situation may call for the elegant perfect shot. You want to be prepared for those moments and know you have it in your back pocket. You want to be able to win a winner's game, but most of the time you want to keep the ball in play. You just want to stay in the game long enough to let the magic of compounding do its thing. You need to be able to win a loser's game. That's all for today's piece. I hope you enjoyed it. I hope you learned something, and I hope you'll share it with others. As always, until next time, stay curious, friends.
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