A Poker Player's Advice for Goal Selection
8 Jan 2022 · 7 min
In the Day 8 episode of the Connect the Dots podcast recorded on January 8, 2022, Matt Ragland recommends Annie Duke’s book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts. He explains how Duke’s poker‑based decision‑making framework can be applied to personal goal selection. Ragland describes the common fear of choosing the “wrong” project and argues that treating goals as bets—small, repeatable decisions made under uncertainty—generates data, builds expertise, and improves confidence over time. He reads a passage from the book’s “Life is Poker, Not Chess” chapter, emphasizing comfort with uncertainty and the practice of estimating odds. Ragland ties this mindset to modern venture‑capital thinking and personal productivity, suggesting that each bet, whether successful or not, yields learning (e.g., improved writing skills from a failed YouTube channel). He promotes his own course, The Productivity Power‑Up, noting the enrollment deadline of January 10, and encourages listeners to read the book to enhance their decision‑making.
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Good morning everyone and welcome back to day 8 of the Daily Dot, the daily version of the Connect the Dots podcast. It's January 8th, 2022. It's a Saturday, so I'm happy to be coming to you from snowy Nashville, Tennessee today. And what I want to share with you on this Saturday is a book recommendation, one I've been reading through again, and it's called Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts by Annie Duke. Now, Annie Duke is the most accomplished female poker player in the world, and just flat out one of the best and most accomplished poker players in the world. So that's how she got on my radar. I don't play as much poker as I used to, but I used to be really into it, and so I heard about Annie through that way. I believe she's also been on the Tim Ferriss podcast, but this concept of thinking in bets came to mind for me again this week because I've been receiving a lot of emails in relation to my course, The Productivity Power-Up, and one of the most common questions is, how do I choose which goal of the many that are in my head to pursue, to make progress on, to dedicate myself to, because, and this is the fear in the back of our heads, what happens if I pick the wrong goal? If I pick the wrong project, I will have wasted valuable time. And trust me, I understand what that feeling is like. It's really hard to trust ourselves, and often, We want someone else to just tell us, be it a boss, a parent, a spouse, a friend, a mentor, a coach. We want them to tell us, hey, you should do this. And sometimes that's really valuable. But one of the dangers in this subconscious thinking of, hey, can you just tell me what to do, is that it makes it really hard to trust ourselves. And if you don't have the courage and the inherent personal trust to make that choice, then it's easy to blame other people, especially subconsciously. So it comes to this point where you really do have to make a decision and live with the consequences. Now, there's a lot of other things that I could say about this, like that nothing that you do is wasted. You gain a lot of experience and expertise. When it comes even to your failures. It's like Thomas Edison saying, I haven't failed 10,000 times on the light bulb. I have 10,000 ways that a light bulb doesn't work. And that has entered our productivity lexicon and lore to where it doesn't quite have the same impact. But essentially what Duke is saying in this book is that when we're thinking of our goals or our decisions as bets, then we're able to generate so many more data points. And it can often be this way in life. In fact, modern venture capital really works this way, that the right decisions, the right bets that you place often pay for all of the bets that you missed in the past and may miss in the future. The projects and the goals that you pick can be very similar. If you make the courageous decision to focus on something, then you start to learn, was that a good bet or was that a bad bet? And you even start to narrow down your selections to say, okay, maybe the project overall was successful, but I can identify some different ways that like this was a bad part of the bet and you can start to optimize those things. You can also see that something in the big picture wasn't as successful as you wanted it to. Maybe you wanted to start a YouTube channel or writing practice and you didn't like get the number of subscribers or views that you want, but you can look at it and say, my writing, my storytelling, my communication has really improved. And that was a good bet on myself to pursue and develop those types of skills. There's a passage in the book Thinking in Bets. This is on page 28 in the chapter Life is Poker, Not Chess, which is another concept of that I've really grown to love. So I'm just going to read this to you. What good poker players and good decision makers have in common is their comfort with the world being an uncertain and unpredictable place. They understand that they can almost never know exactly how something will turn out. They embrace that uncertainty, and instead of focusing on being sure, they try to figure out how unsure they are, making their best guess at the chances that different outcomes will occur. The accuracy of those guesses will depend on how much information they have and how experienced they are at making such guesses. This is the part of the basis of all bets. Picking projects, goals, habits is very similar. I received an email today that said, if I could know that I was going to have a positive outcome, then I would absolutely pursue this thing. But the nature of our decision-making and our selection process means that we don't have that outcome written in stone and assured and set aside. And to be honest, like, how interesting would it be if all the boxes were checked? It's like we talked about from Joseph Campbell yesterday. If you can see your life's path laid out, then it's not your life's path. Thinking in bets requires us to make a series of small bets over time to learn from the results and to be intentional as our experience and our expertise grows. The more that you're willing to make decisions and make bets on the projects that you pick, the more that this expertise and experience will grow, and you will become more confident at making better bets in the long run. I highly recommend checking this book out. It is one of my 22 books for 2022 video and podcast that will be coming out next week. So make sure you check this out. Again, it is Thinking in Bets. Making Smarter Decisions When You Don't Have All the Facts by Annie Duke. Thanks so much for listening to this daily edition of the Connect the Dots podcast. Don't forget that in a couple of days on January 10th, the digital doors are closing for the Productivity Power-Up. Just go to productivitypowerup.com to get all the information you need and to sign up and join us for this next cohort. Thanks so much for listening, and I will see you tomorrow. Bye.