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Unlocking the Secrets of Decision Making: The Weird Jailer

Unlocking the Secrets of Decision Making: The Weird Jailer

Hey There 👋,

Last Friday, we organized an afternoon book club session in the office to discuss decision-making strategies. I would like to extend the key learnings with you guys through this newsletter as a short series. 📚💭

The first story I wanna share is called the “weird jailer” 👮‍♂️ from the book “The Intuition Pump and Other Tools for Thinking” written by Daniel Dennett. The story goes like this: there's a strange jailer who opens the prison gate in the middle of the night when all the prisoners are asleep 😴.

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And Dennett follows up with a question: should the prisoners be considered free in this case? What do you think?

At first glance, it seems like the answer would be yes if a prisoner happened to be awake and took advantage of the opportunity to escape. However, upon closer examination, we see that the prisoners who were asleep when the gate was open never truly had the option to escape. 😮

This story is a powerful reminder to consider the context and external environment when evaluating a situation. The concept of missed opportunities is something that we often look back on with regret. It's easy to think about all the times we could have made a different decision that would have led to a better outcome. For example, not investing in Bitcoin or unicorns in their early stages 💰. However, it's important to remember that those opportunities may not have truly existed for us. We may not have had the knowledge or resources to take advantage of them at the time. 💡

It's important to keep in mind that it's easy to look back and see what we could have done differently, but much harder to make the right decision in the moment. This is why it's crucial to consider the context and external environment when evaluating a situation. By doing so, we can make more informed decisions and avoid the feeling of regret that comes with missed opportunities. 🌟

The value of the weekly digest newsletter

This story not only teaches a moral lesson but also made me contemplate the value of this weekly digest newsletter for my audience, particularly in the age of Artificial Intelligence. Due to word count limitations and your busy schedule, it's impossible for me to delve deeply into specific topics.

If you are hoping to get customized solutions to particular problems, consulting chatGPT or any relevant expert would definitely be a better option.🤔 However, I believe my competitive edge lies in my strong curiosity, which leads me to absorb a variety of knowledge from books, podcasts, and other sources covering various fields such as decision-making, history, and technology. I am eager to share these interesting ideas and methodologies with you.

Instead of positioning myself as a creator or expert, I see myself as a curator who presents the potential of these interesting ideas 💡. By incorporating these ideas into your work and daily, they can hopefully guide you to a door to some interesting ways of doing things that you haven’t been aware of previously, maybe like an alarm that wakes the prisoners to possibility to escape from the prison.

For example, we previously discussed the importance of timing in "The Forgotten Factor: How Timing Trumps All Productivity Hacks " 🕰️ (check that out if you haven’t read it yet!). The next time you ask ChatGPT to plan your work schedule, you might consider asking it to factor in your cognitive ability throughout the day to optimize your productivity.

As always, thank you for reading, and I will be sharing with you the lessons I learnt from another decision-making classic that I shared in the book club, “Thinking in Bets” written by the famous poker champion Annie Duke. So stay tuned! Don't forget to share this newsletter with your friends and colleagues, and spread the knowledge! 💡

Ciao,

Sherman


Things that I found interesting this week:

📚 Book — “The Intuition Pump and Other Tools for Thinking” by Daniel Dennett 

I recommend this book, "The Intuition Pump and Other Tools for Thinking" by Daniel Dennett, to you since I know you might be interested in improving your critical thinking skills and learning the right way of thinking to avoid being trapped by misleading information. The book is full of interesting concepts and examples, such as the weird jailer, who opens the prison gate in the middle of the night when all the prisoners are asleep, and Sturgeon’s Law, which states that 90% of everything is crap. By reading this book, you would significantly uplift your capabilities of critical thinking and learn to make your comment or critique on the 10% that really matters.

🎬 Video — How to Make Difficult Decisions (without overthinking) by Ali Abdaal

I come across this really cool video on decision-making and I wanna share this with you. Ali Abdaal is a popular YouTuber who curates ideas on productivity, studying, and lifestyle. In this video, he talks about how to make difficult decisions without overthinking. One thing I particularly like is the idea of creating a mental board of advisors, which he mentions at timestamp 02:26. I am personally adopting this approach in some of the time that I gotta make a key decision by including top problem-solvers from different fields and time periods, such as Elon Musk, John von Neumann, and Omae Kenichi, and asks AI to imagine how they would solve a specific problem. It's a great way to get different perspectives and creative insights.

📃 Blog — How to Create a Mental Advisory Board - Corey Wilks, Psy.D. (coreywilkspsyd.com)

I found this article pretty inspiring to me as it highlights the importance of having a supportive network in the form of a mental advisory board. The article provides a step-by-step guide to creating your own personal board, which can consist of friends, family, mentors, and even fictional characters. The board can offer different perspectives and insights, help you make decisions, and support you when you face challenges. I particularly like the idea of having fictional characters on the board as it allows for a wider range of perspectives and creativity. Overall, this article is well-written, concise, and practical. Give it a read if you're looking to improve your decision-making and well-being.