If You Only Read One Book This Year, Make It This

This book changed the way I make decisions. It didn't come from a CEO, a business school professor, or a billionaire investor. It came from Annie Duke, a world-class poker player who spent 20 years at the table and won millions. Poker is interesting because you can make a good decision and still lose money, or make a terrible decision and still be rewarded. You never know for sure whether you're smart, lucky, or just emotional. That's why thinking in bets matters—because your career, your money, your relationships, and your biggest life choices work the same way. But this video is not just a book summary. I'm going to turn Duke's ideas into a practical system for making better decisions when you don't have all the information. I'll show you how to avoid emotional pitfalls, how to separate skill from luck, and I'll share a framework called Ava that can help you when you can't see around the corner. This might save you years of heartache. Let's dive in.

The most counterintuitive insight we miss is this: good results are bad teachers. The most dangerous teacher in your life is accidental success. Let's say someone gets really drunk late at night and decides to drive home instead of calling an Uber. He might speed through three red lights at 2:00 a.m. and still get home safely. That's a good outcome—a great outcome—but it was still a terrible decision. When something works out in your favor in spite of you, your brain assumes that you made a smart bet. But the biggest mistake here is that we judge the quality of the decision by the result it produces, even though they may not be connected. That drunk driver will convince himself that nothing happens when you drive under the influence of alcohol, and that could prove fatal to him and others. This is one of the central ideas of the book. In poker, you can play the best hand and still lose, or make a terrible bet and still win. That gap is where people get confused about their own judgment. This happens in business, in our careers, on Wall Street, in relationships—everywhere. There are traders I know who believe they have a magic touch and their trades never go the wrong way, until of course they do and they lose everything.

The same goes for founders and CEOs. I was the CEO of an AI company, and we became the 20th fastest-growing tech company in the US. Was that because I was a visionary CEO? I wish. We were simply the company solving the right problem at the right time, and it worked out. Five years before or five years after, the same company wouldn't have worked. The tide is way more important than who's rowing the boat. Our decisions might be clean, but outcomes are rarely clean. They're usually a mix of skill, luck, timing, and emotions.

That should give us humility, and it should help us watch out for our self-serving bias. When we win, we think it's because of our skills. When we lose, we blame our luck. But when others win, we say they got lucky, and when they lose, we say they didn't have enough skill. The results may come back amazing or awful, but that does not make you a genius or a victim. The only useful move is to pull the result apart and ask, "What part was skill? What part was luck? And what can I do better next time?" These questions sound pretty simple, but they're hard to put into practice.

Let's first figure out how our skills and luck get tangled up when we make decisions. That's where we'll find our first tool for decision-making. That's where we go next.

A few years ago, I had a choice between two paths. One was a CEO role at a very cool tech company—a startup we'll call Company A. There were about 150 people, and it was growing fast. I had been in the CEO chair before, so it felt familiar. The board and I had many conversations, and the chairman had already sent me the offer with compensation, equity, and all of that. Then, just before the day I was about to sign, another option showed up. It was a COO role at Company B. That company was a public company, much bigger, with a very strong market position and already worth about $10 billion in market cap. I loved the CEO and the mission. I went through my decision framework carefully and thoughtfully, and I ended up choosing Company B. In the next few years, Company A surprisingly faced tremendous growth challenges and eventually had to shut down, while Company B's stock went through the roof—up by more than 500%.

In retrospect, the decision I made looks like a brilliant move. But here's the twist: a few years later, I had already moved on from the company and retired, but the industry dynamics changed suddenly. The company’s stock plummeted and it wiped out almost 90% of its value. I still had stocks in there. I should have sold the remaining positions, but I didn't, and it cost me a fortune. This is the heart of what Annie Duke teaches in Thinking in Bets. You can play a hand with perfect skill, get lucky, and still lose. We have to get ruthless about separating what is skill and what is luck. Let's unpack my decision process the way she would. The first decision—to choose Company B—was skill. I suppressed my ego, didn't get seduced by the CEO role, and made the right choice. But the rise in stock price that followed was pure luck. Finally, not selling the stock at the right time was just my dumb mistake. It was my greed, my emotional attachment to the company, and my delusion that it would come back. It wasn't just bad luck. It was just a dumb mistake. This has happened to me many times, and it will happen to me again. If you are ambitious enough to play high-stakes games, it will happen to you too.

Here's the tool: don't ask, "Was I skilled or lucky?" because you're most likely both. Also, your self-serving bias has already rigged that answer. Picture someone else making the exact same move, and then put them on a dial from pure luck to pure skill—90/10, 50/50. That's the most honest number you can come up with. Your job is not to look back and beat yourself up over the luck you couldn't control or the skills you had or didn't have. Your job is to audit the process, learn the lesson, and get ready for the next bet. More importantly, know when to fold. That was my mistake—I didn't get out on time. By the way, if you're interested in reading more about tools and frameworks like these, you can subscribe to my newsletter as well. I write it every Tuesday: one insight, one tool, one practice. The link is below, and it's totally free. The key takeaway is this: sometimes the same decision can be smart, lucky, or foolish at different points in your life story. That's life. Now, some of you may say, "Well, then you have to wait until you have all the information. Then you'll know which one is which." Well, that's a fallacy, and we'll see why next. We keep waiting to feel certain before making big decisions, and that's why we wait forever. In "Thinking in Bets," Annie makes a simple point: every decision is a bet against the future. You're choosing between multiple futures. You cannot fully see a job, a house, a partner, or a company. You're not supposed to know everything. If you knew everything, it wouldn't be called a bet. You never have perfect information. Also, having more information doesn't always help. A Columbia researcher named Sheena Iyengar found something very interesting in a grocery store. She set out a table with six jams to taste. The next weekend, she came back to the same station, set up the same table, but put out 24 jams for people to taste. The bigger display and more options attracted more people to the table. But when it came time to buy, the people who saw six jams bought more than the people who saw 24. More information and more options didn't give them more certainty to buy the product; it just made the decision harder. Sometimes more information can feel safer, but most of the time it's just causing analysis paralysis. It's just another excuse not to move forward. I think this is the key difference between chess and poker. Chess is hard, but the entire board is clearly visible. You can see every piece and the current positions. But when it comes to poker, the truth is hidden. You don't know the other person's cards, you don't know what card will come next, and you don't know when someone is bluffing. That is much closer to our lives, because in life you never get to see the full board. Here's one practical move I use: I make a two-column decision table. In the first column, I write all the known facts—what is visible, what I know. In the second column, I write all the hidden cards—what is unknown, what I am assuming, what I am hoping to be true. Once you separate what is known from what is unknown, your decision gets cleaner. Now, even if you don't have all the information, you still have to make the bet and ask what beliefs you're going to be betting on. That's where we go next. There is a famous study called "They Saw a Game." There are two universities, Dartmouth and Princeton, both in Northeast America. Researchers had students from both universities watch the same football game. Their own universities were playing against each other—the same plays, same penalties. Yet Dartmouth fans swore Princeton played dirty, and Princeton fans saw the exact opposite. They saw the game through the team they already believed in. That's why some beliefs can start distorting what you see. That is also one of the core ideas in "Thinking in Bets": that every decision is a bet built on what you believe. This is why fake news works so well—it feeds into what we already want to believe. For example, for years, people have clung to this headline that red wine is good for your heart. Why? Because people drink red wine when they come home and want to relax in the evening. Research has since debunked that myth clearly many, many times over, but the belief has stuck around because it tells us what we want to hear. What's the action? Use these two moves. Number one: replace your binary thinking with probabilities. Instead of saying right or wrong, or good or bad decision, ask, "How confident am I? Am I 70% sure or 80% sure?" Number two: ask the key question to yourself—"Do you want to bet?" That's a great question. It's from the book. When you feel certain about some belief, imagine putting $100 or $1,000 on that belief. It will force you to examine and define exactly what you believe in and based on what evidence. It's better to start asking why you believe it. Okay, we've thought about our luck, our skills, our beliefs, and now we've come to a point where we're ready to make a decision. We're going to need a framework for it. That's where we go next. In the Odyssey, the protagonist knew about the siren song. He knew it would hijack his mind. Sailors who had heard it before had lost control and crashed into the rocks. Before he heard those songs, while his head was still clear, he asked his crew to tie him to the ship's mast and ignore anything he said once the song began. Today, psychologists call it the Ulysses contract—a rule your present self makes to protect you from your future self. The book gives us the same type of principle, but we have to go beyond the book now and build our own practical framework to put that advice into action. This is where I use a decision-making framework I call AVA: expected value analysis. Emotions can have a seat at the table, sure, but AVA gets the first vote. It's a four-step process. First, before making any decision, map out the scenarios. Put four or five branches on paper: great success, moderate success, minor failure, and catastrophic failure. Once these possibilities are on paper, the fog starts to clear. Second, assign payoffs to each of these options. Put a dollar figure on each branch. How much will your gain be if it's a success? How much will you lose if it's a failure? By the way, you don't have to value your payoffs in terms of hard cash—include whatever matters to you: your time, your reputation, your health, the impact on your family, anything. Third, assign the odds. Give each branch a probability score. What is the likelihood of that outcome happening? Do it based on the information you have today. The fourth and final step is to calculate the expected value, which is to multiply the payoff by the probability. The evaluation process is more important than the actual numbers because you can stress test all the scenarios. Look at the worst-case scenario. Once you put the numbers down, imagine it's twelve months from now and everything has failed completely. You can write down your version of how it failed and what happened. When you script that detailed disaster story before it has happened, your brain builds the exit ramps before the crash ever occurs. That is the point of AVA. It doesn't make your decision certain. It helps you understand why it's uncertain, and it helps you manage the most dangerous side effect of your decision. And that's where we go next. In poker, there is a condition called tilt. It's the exact moment your last hand completely infects your next move. You play a hand correctly, lose anyway, and your anger, fear, frustration, and wounded pride—all of them take over. Or the exact opposite might happen, too: you win big and you start betting as if you're invincible. Both extremes are illusions. This is one of the book's key messages. And here's where the biggest trap is: when you start tilting, it is obvious to everyone else, but invisible to you. Tilt serves you a very toxic self-punishment. When you fail, you start thinking, "Why do I always screw things up?" and you're locked into that world. You can't see outside of it. That is one of the biggest enemies of making great bets: regret. That's what keeps the last hand alive inside the next one. But regret after a loss is part and parcel of how we all feel as human beings. There is nothing you can do to change what is gone, what is lost. But regret should heal, not harm. If you lose money, it doesn't mean you should get out of the market just when it's recovering. I've done that. If you get fired, it doesn't mean you should stop applying to the next amazing job. I've done that, too. If someone breaks your heart, it doesn't mean you should stop believing you could be loved again. This happens to all of us. But this is where we have to go beyond the book. The real lesson is not about card games. It's about realizing that outcomes can lie to you, your beliefs can distort you, and your past regrets can paralyze you. All of it is inevitable. It's going to happen. But a regret is only wasted if it doesn't improve your next bet. One of my favorite songwriters, John Prine, has a song with this phrase I love: "the blind spot of regret." Because the past follows you everywhere you go. We hang it like a relic on our rearview mirror and we keep glancing at it while we're trying to drive forward. But the rearview mirror can't steer the car. You can hang your regrets where you can see them and then drive forward. Take the new turn. Make the new bet. The road ahead only cares about how lucky you can get. I'll see you next week. Thank you, and I love you.