After revisiting How to Read a Book and synthesizing it (see here), I realized that I prefer synoptical reading and had spent most of the year doing it. Hence, in the library section of this site, you see that each book lists the number of books it’s connected to. I also read analytically, but less often, and honestly that isn’t my first choice.

Another thing I realized is that I haven’t been consistent in doing Stage 1 (which, ironically, I added to the process). Stage one is “Define the problem you need to solve or the topic you want to understand.” But most times, I pick up a book based on what feels good at the time. I read it, and if it mentions another book, I read that book too. The result is that I’m not reading to solve top-of-mind problems or understand the very issues slowing me down. I’m just gathering knowledge that might not be what I need to move forward.

I thought about it today and realized that it takes effort to crystallize a specific problem. It’s not easy or natural for many people, which explains why so many early-stage founders can’t articulate the problem they’re solving (see here). But, as Kidlin’s Law says, if you write a problem down clearly, then the matter is half solved.

So, going forward, I’ll write down the problem I want to solve or the topic I want to understand better before I start reading synoptically. My hunch is that I’ll read more intensely and accelerate my progress by focusing on that problem or topic as I read.

As part of my Thanksgiving challenge (see here), I said I’d synthesize three reads. This is the first synthesis.

A few years ago, I got serious about reading books to better understand investing. I decided to start on the right foot, so I read How to Read a Book. I remember that this book resonated with me, but it’s been a few years. So, I decided to brush up on it and share my takeaways to reinforce my learning. This book was written in the 1940s. It isn’t as concise as modern books usually are, and the meaning of the words isn’t always obvious, so digesting and understanding it took more time.

The main idea that resonated with me is this:

Synoptical reading is the highest level of reading. Reading multiple books on the same subject helps you gain a deep understanding of a topic from various perspectives. That deep understanding positions you to think independently and creatively to form your own conclusions.

This idea stuck with me because it matches a pattern I’ve noticed. Many people who’ve achieved outsize success read synoptically to improve decision-making and accelerate problem solving. They don’t start from scratch; they leverage what others have already figured out. They stand on the shoulders of those who came before them.

Before I get into how to read synoptically, I want to share something I find helpful to know, namely that there are four levels of reading:

• Elementary reading – Understanding what a sentence is saying. Think grade school.
• Inspectional reading – Understanding the main ideas when time is limited. This involves skimming (i.e., pre-reading) and then superficial reading.
• Analytical reading – Understanding the main argument of a book. This is intense and active (not passive) reading.
• Synoptical reading – Understanding a topic by comparing different perspectives from several books and coming up with your own conclusions.

So, how the heck do you read books synoptically? It’s a simple two-stage process (I added a third stage). Here are the stages and steps:

• Stage 1 (my addition): Define the problem you need to solve or the topic you want to understand.
• Stage 2: Identify relevant books.
  
  • Step 1: Create a list of relevant books. The library and notes or bibliography sections of other books (see here) are useful
  • Step 2: Inspect each book via inspectional reading (i.e., skimming and superficial reading).
  • Step 3: Narrow your list to the most relevant books.
• Stage 3: Synoptically read relevant books.
  
  • Step 1: Find relevant passages. Identify passages that help you solve your problem or understand your topic. Be selfish and find the parts of the books that serve your interest. You don’t have to read the book the way the author intended.
  • Step 2: Bring the authors to your terms. Authors may use different terminology to describe similar things. Come up with your own language and convert what you’re reading into it so it makes sense to you.
  • Step 3: Ask the right questions. Create a set of questions you want answered by the books. The answers should enhance your understanding of your topic or give you ideas about how to solve your problem. Every book won’t answer every question, and that’s okay. Example questions include: Does this problem or topic exist? How can we recognize it when we see it? What does this idea look like when it happens? What happens because of it?
  • Step 4: Define the issue. Authors may have differing views on the topic or problem. Identify the central question or issue underlying their disagreements.  
  • Step 5: Analyze the discussion. Look at how each author answers the central issue you identified, compare their arguments, and understand how their views relate to—or conflict with—each other.
  • Step 6: Think. Use your analysis to develop your own conclusions about the topic or solutions to your problem.

That’s it. That’s how you read multiple books synoptically.

So, what if you want to read a single book? Good question. That’s where analytical reading comes into play. Here are the stages and steps:

• Stage 1: Figure out what the book is about.
  
  • Step 1: Figure out what kind of book it is and what topic it covers.
  • Step 2: Describe the book’s main point in one short sentence.
  • Step 3: Show the book’s skeleton—break it into its major sections, figure out how they connect, put them in order, and create an outline.
• Stage 2: Figure out what a book is saying.
  
  • Step 1: Figure out what the author means when they use certain important words or phrases.
  • Step 2: Identify the author’s main claims by focusing on their most important sentences—and make sure you understand those claims.
  • Step 3: Understand the reasoning the author uses to back up the main claims by following the reasoning across multiple sentences or paragraphs.
  • Step 4: Figure out which of the questions the author set out to answer were answered, which ones weren’t, and whether the author knew they left some questions unanswered.
• Stage 3: Criticize a book.
  
  • Step 1: Understand the author’s perspective first. Don’t judge the book until you fully understand it. You can’t agree or disagree until you can accurately explain what the author meant. This usually requires outlining and interpreting the book.
  • Step 2: Don’t disagree with the author just to be contrarian or combative—your disagreement should be rational.
  • Step 3: If you disagree with the author, back up your criticism with knowledge—that is, evidence, logic, or clear reasoning, not personal opinion.
• Stage 4 (my addition): Reach your conclusion.
  
  • Step 1: Crystallize your thoughts about what you’ve read.

The steps listed above aren’t complex. They somewhat remind me of how I read textbooks in college, which was a period that felt like rapid-paced learning. So reading this way is definitely doable.

I’m not going to lie; this book wasn’t an enjoyable read. But the framework it provides around synoptical and analytical reading were worth the effort. I think they’re useful for anyone serious about self-educating and looking for ways to add more structure.

I’m glad I synthesized the ideas from this book that I found useful. It really ingrained the ideas in my brain this time around. Hopefully, this synthesis will be helpful to others, too.

I’m wrapping up my blog posts about the three books I synthesized as part of my Thanksgiving challenge (see here). As I was working today, I thought about several insights:

• The synthesis of the books happened within the time frame I planned (i.e., Thanksgiving weekend). But sharing what I learned in a way others could easily pick up took longer than I estimated.
• Creating a post that summarizes an entire book is something I can do, but it’s likely to be rare.
• Creating the digest is helpful, albeit painful and time-consuming. It forces me to pick out the most important points from the book. But the process of turning it into something useful to others forces me to understand the material deeply. I didn’t realize how much of what I’d consumed, even after I created the digest, I didn’t fully grasp. Sharing is a force function in understanding.  
• The more poorly a book is written, the more work it is to create a digest and post. One book, written in the 1940s, was wordy and poorly structured. Piecing together what the author was trying to convey in a simple way that people could grasp quickly took more effort. Good content, but not presented well.
• The concept of ideas is starting to resonate with me. What ideas in a book got me excited, and why? If I can answer those questions, those ideas are probably worth sharing.
• Breaking complex frameworks down into something easily understood by others (and giving myself a quick reference) is something I toyed with and enjoyed. Lots of work, but curation and simplification are valuable to others (and will be valuable to my future self when I need my memory jogged quickly).
• You don’t deeply understand something unless you can communicate or teach it to others in a way they can easily grasp. If I want to force myself to understand something deeply, I should make myself write a blog post about it.
• Investors who teach or openly share what they know may have a secondary motive. It helps people, which is great. But it also forces them to learn things more deeply, which likely has a positive impact on their decision-making and investment returns. This is likely true for other professionals outside investing, too.

Those are a few quick takeaways from my latest holiday challenge. I’m glad I decided to do it. It reminded me of the value of synthesizing my reading, and it’s forcing me to figure out how to develop the habit of doing so consistently.

Earlier this year, I shared a video (see here) that Andrej Karpathy made about how he uses large language models (LLMs). According to his website, Karpathy was “a research scientist and founder member at OpenAI” before spending several years at Tesla as Senior Director of AI. His video jumped out at me because he uses LLMs to help him read and understand books and research papers. He did this manually, and he described how painful it was, which I summarized in this post.

He’s taken his habit of reading with LLMs even further and developed a process with three passes: first, manual reading; second, having the LLM “explain and summarize”; and third, Q&A with the LLM. See his post about this here.

In addition, he solved his own pain: He shared that he’s built a simple tool for implementing this process with less friction. It enables him to read books in ePub format and feed the text of the book to the LLM, so he can ask the LLM questions while he reads. See more details in his post here.

He shared the code for his tool so others can use it, which is pretty cool. It’s available on GitHub here.

This sounds really interesting, and I can’t wait to give it a try.

I’ve been curious about the “Great Inflation” period of the 1970s. Reading about decisions in the 1960s and 1970s that led to it was eye-opening. A few months ago, I came across a biographical anthology that caught my eye because it talked about what happened after that period—specifically, how the Great Inflation contributed to the craziness of the 1980s: the junk-bond boom, the leveraged buyout wave, the birth of private equity, and the eventual S&L turmoil.

Dangerous Dreams was interesting because it wasn’t just a biographical anthology that talked about several people in isolation. Rather, it discussed each person’s story and the role they played in the creation and evolution of the junk-bond mania of the 1980s. It was the story of how each person contributed to the broader story and how these players influenced each another.

Louis “The Junkman” Wolfson, Charles Merrill, conglomerate builder James Ling, Michael Milken, Ivan Boesky, T. Boone Pickens, Carl Icahn, Rudy Giuliani, and others were profiled.

The main character, the man who helped birth the junk-bond market, was Michael Milken. The book details his rise and spectacular fall. It does a great job of explaining how an unheard-of book-on-bond analysis sparked Milken’s ideas that led him to build and control the junk-bond market throughout the 1980s.

I learned a lot from this book, especially about how the 1970s created an environment in which the stock market valued blue-chip companies at significantly less than their value and high-growth companies were pretty much shut out of the bond market—all of which led to craziness on Wall Street in the 1980s.

Anyone interested in Michael Milken, T. Boone Pickens, the origins of the junk-bond market, the savings and loans crisis, or how private equity got started should consider reading Dangerous Dreamers. You’ll come away with insights into all the above and more.

Last year, I was creating a blog post series for each book I read. After reading a book, I had to go through all my notes and highlights to create a digest in the form of a Google doc that detailed, by chapter, all the important points in bullet format. The result was a summary of each book, by chapter. Most were between 5% and 10% of the book’s length, so for a 250-page book I’d have a Google doc of 12–25 pages. Creating a 12–25-page Google doc takes a ton of time.

I read a book a week, so I had to create these digests weekly. In addition, I was publishing a series of blog posts on each book and experimenting with podcasting by creating a series of episodes on each book. It all felt unsustainable, so I didn’t continue.

I’m reflecting on this today, and I realized a few things:

• Too many new things. Creating the podcast was a ton of effort. Creating the book digest was a ton of effort. Writing a blog post series was a ton of effort. Taking on all these new activities at once likely contributed to it feeling unsustainable. I was never able to find a “groove” for any of the three that felt like second nature. I was just trying to get through it all, but I never felt comfortable with any of it. In hindsight, I should have started with one, gotten that under my belt, and then moved to another.
• Synthesis enhanced my understanding. Creating those digests, which were the foundation for the blog post series, forced me to read analytically. Doing so led to a deeper understanding of what I was reading and helped me uncover more insights and achieve a level of retention I hadn’t experienced since college. When I stopped creating digests, I got less from the books I read. In retrospect, this step, which felt painful, was tremendously beneficial.
• AI can’t save me. I thought I could use AI to help me. My idea was that I could feed AI my highlights and notes from a book and it could create a digest for me. I now realize that this detracted from my understanding of what I read. Reviewing and synthesizing my highlights and notes to create a digest wasn’t fun, but it enhanced my understanding by forcing me to think more deeply about what I’d read. I had to identify the book’s key points, evaluate whether I believed them, and determine whether they supported the book’s main arguments or ideas. Outsourcing that to AI would get me a digest quicker, but I wouldn’t learn, understand, or retain as well—which is the whole point of reading these books to begin with.

I’m really glad I’m doing this Thanksgiving challenge now (see here). I think it’s the start of my figuring out how to sustainably synthesize and share what I learn from books. I’m not trying to check boxes; I’m trying to learn as much as possible from the books I read and share it openly so others can learn too. That’s something I’d strayed away from a bit, but I’m laser focused on it now.

I’ve read several biographies of and books by notable investors who started their own investment firms: Howard Marks, Warren Buffett, Charlie Munger, T. Rowe Price, Mohnish Pabrai, Joel Greenblat, Adam Seessel, and more. They all mention value investing and its founder, Benjamin Graham. Graham was the only boss Buffett ever had, and Buffett still speaks well of his mentor, some 70 years after working for him. All this intrigued me and made me want to learn more about the man so many people hold in high regard. So I read The Einstein of Money, the biography of Benjamin Graham.

After reading this book, I understand why Graham developed the value-investing concepts that have endured for a century. His approach was the result of personal and professional pain. Graham watched his widowed mother struggle to raise her children, which left a deep scar on him. It made him aware of the value of money and motivated him to obtain it so he could have freedom and avoid what he endured as a child. After starting his own Wall Street investment firm, Graham lost substantial money in the 1929 stock market crash and the ensuing Great Depression—so much that his partnership almost went bankrupt and he had to move his family to a cheaper home and generate side income as an expert witness in legal cases to make ends meet. Graham reflected on what went wrong to cause all this pain. This led to insights that shaped his value-investing framework, which he documented in his investing classics Security Analysis and The Intelligent Investor.

Graham went on to tremendous professional success, becoming a wealthy and highly respected investor and professor at Columbia and UCLA. But his personal life was filled with highs and lows. The lowest points were the deaths of his two sons. And he was imperfect and dealt with personal challenges, some of which led to marrying three times.

Graham was a brilliant person, and I now understand why so many accomplished investors respect him. His value-investing principles have endured the test of time, shaped the thinking of great investors like Buffett, and led to a cult-like value-investing movement.

I’m glad I read this book, and I want to read The Intelligent Investor too. Anyone interested in learning about the man Warren Buffett names as a major contributor to his success should consider reading The Einstein of Money.

A few weeks ago, I read The Success Equation by Michael J. Mauboussin. He said that checklists are an important part of improving your decision-making process for activities influenced by luck. He mentioned the different types of checklists and a book that dives deeper into them.

The references to checklists stuck with me and reminded me of what Charlie Munger said about checklists. (See the post I wrote about that here.) It also made me want to learn more about the reasons checklists are so powerful.

So I read Checklist Manifesto by Atul Gawande, the book Mauboussin referenced. It delves into why checklists are used in industries such as aviation and construction. And why they’re effective at improving outcomes (and preventing disaster). A central point of the book is that the world is becoming more complex. It’s hard to remember everything, especially in high-pressure situations. Simple checklists help improve outcomes in complex situations by reducing errors of omission—missing important steps—and errors of ineptitude—failing to apply knowledge we already know. Going through a checklist forces consistency in how you think and what you do, preventing critical items from being overlooked or forgotten and thereby improving outcomes.

The book also describes the two main types of checklists and when it’s appropriate to use each: do-confirm—you perform tasks from memory and then verify them—and read-do— you follow steps, line by line, in high-stakes or unfamiliar situations.

An interesting note: the author is also a surgeon, so the book details his experience in trying to get hospitals around the globe to adopt surgical checklists (spoiler . . . checklists significantly reduce patient complications and death rates!).

I also found his research on the aviation industry, specifically the origins of why the industry instituted and relies heavily on checklists before takeoff and during emergencies, to be eye-opening.

I first read Expectation Investing by Michael Mauboussin this past summer, and I ended up reading that book twice and starting to read all of Mauboussin’s other books. This post is about the fourth of his books that I’ve read in the last few months, and it didn’t disappoint.

The Success Equation is about understanding the impact that luck and skill have on your successes and failures. The book provides a framework for understanding, in advance, how much skill and luck will impact a decision or activity. Understanding how what you want to do is affected by skill and luck can alter your planning, expectations, learnings, and a host of other things.

This book is full of things I’ve found helpful, two of which I’ve written about already:

• Rationality quotient (RQ) matters more than intelligence quotient (IQ)
• How checklists tame luck

Another concept that stuck with me is what he called the “luck-skill continuum.” Mauboussin explained how to gauge the extent to which an activity is influenced by skill and luck by visualizing it on a continuum. He then explained why the sample size required to draw a reasonable conclusion about future expectations differs for activities heavily influenced by skill vs. luck. He also explained reversion to the mean and why it impacts activities of skill and luck differently. I have lots of notes and highlights in the chapter on the luck-skill continuum that I’ll revisit often.  

This book was a great read. Anyone interested in improving their chances of success by improving their decision-making should consider reading The Success Equation.

I shared earlier this week that I’m reading The Success Equation by Michael J. Mauboussin. It outlines a framework for assessing the influence of skill and luck on your decisions (many life outcomes are a combination of both) so you can increase the chances of getting a successful outcome. It’s a good book about improving your decision-making by understanding the impact of luck and skill on successful (and unsuccessful) outcomes.

As I’ve said many times, books are a great way to find other books. One of the key concepts Mauboussin discusses is that to improve your skill in activities where luck has a greater influence than skill, you must focus on the process used to make decisions. The idea is that good decisions can result in outcomes we don’t want because of the influence of luck. And vice versa: a bad decision can lead to a good outcome because you got lucky. Therefore, a decision can’t be judged by its outcome; it must be judged by the quality of the process and analysis used to make it. He goes into more detail, but that’s the gist. I agree with this.

One of the things he suggested using, because they’re effective tools to improve decision-making processes, is checklists. Charlie Munger said the same thing in Poor Charlie’s Almanack (see here). Mauboussin told the story of a doctor who used checklists to significantly reduce hospital infections and realized how powerful they are. He wrote a book about checklists and how to use them effectively called The Checklist Manifesto.

Munger and Mauboussin can’t both be wrong about checklists. I use them some already, and I want to embrace them for material decisions, especially those that involve luck. I’m going to get a copy of The Checklist Manifesto and give it a read so I can lean into what Munger and Mauboussin have both said.