Confessions of a Clever Fool

Vishal: I used to be a fool. Maybe I still am. But at least now I have a chance of getting wiser.

Bill: What’s changed for you? 

Vishal: Here are seven things:

1. I think about what’s worth pursuing in life instead of just assuming that what I’m doing is worthwhile.

2. I don’t just dismiss things that are out of my current understanding or daily sphere of operation. I’m more inclined to learn something just for the sake of knowing it.

3. I’m able to discern when there’s something wrong with someone’s line of reasoning even if I’m not able to say exactly what it is. Before I wouldn’t even have a sense that anything was amiss.

4. I’m more inclined to pause a conversation to clarify definitions. For example, you and I might both say that we want to help our kids live well. But what do we mean by “well”? What does that mean to you and to me?

5. I’m better at extracting the kernel of truth in what other people say. Before I would try to find something in what they said simply so I could agree or disagree with them. But I wouldn’t put the effort into understanding what they were saying. 

6. Humility: I have a clearer sense of what I don’t know.

7. Patience: I realize that it takes time for me to internalize the lessons I’m learning and to allow those things to change different parts of my life.

Bill: What direction do you think your life might have taken if you hadn’t changed in these ways?

Vishal: I’ve always been pretty good at getting what I want, so there are many roads I could have taken. Back when we started working together, I wanted to become a New York Times bestselling author. I can see a version of my life where I might have done that—a version in which I would’ve been a fake intellectual peddling biased messages in some echo chamber: no substance in my thoughts or writing, no critical reflection, just confirmation bias re-echoing talking points on social media platforms, blogs, or books. 

Maybe I would’ve been using libertarian rhetoric to pump crypto currency like Pomp or Balaji. Maybe I would’ve been using liberal identity politics to pump false claims of social injustice. Maybe I would’ve been using conservative us-versus-them rhetoric to stoke false fears of government robbery. Maybe I would’ve found clever ways of packaging shallow thinking like Naval Ravikant or Tim Ferriss. Whatever it was, I would’ve worked my ass off to master the echo chamber’s talking points. But I never would’ve  stopped to examine those points. I never would’ve sought out smart people who disagreed with me and worked at understanding their reasons for disagreeing with me. I would’ve instead thought, felt, and acted according to the echo chamber’s script. Mine would’ve been a life straight out of Orwell’s 1984. 

Bill: When did things start changing for you?

Vishal: One of our first talks, you asked me a really uncomfortable question: “Why do you want to be a New York Times bestselling author?” I thought, “Why the fuck not?!” You listened patiently and observed that I sounded like I was just seeking other people’s admiration. I knew you were right. But it took me a while to change my mind. Looking back now, my patterns of thinking, feeling, and acting were aligned with someone like Tim Ferriss—trying to discover the best means of achieving an end without questioning whether the end is worthwhile.

Bill: And now?

Vishal: Now I reflect on the ends that I pursue in life. For example, when we first met, my goal was to be a rich and famous writer. After working with you, my goal is to be a competent writer. You had me reflect on what's worth doing and what's worth writing about. 

I recall feeling frustrated that we didn’t produce a blog post for almost a year. I went into my production mode and demanded that we produce 25 posts for the Think But How blog. Looking back, I see that my old paradigm had taken hold again: production, production, production. I didn’t care as much about learning the craft. I was still chasing shallow goals as a writer.

So the path you got me on was to reflect on things I wanted in life. I started asking myself, “What's worth pursuing?” 

I remember you said that if I wanted to be a better writer I needed to work on being a better thinker and get clear on what I was trying to say. I was like, “What the fuck is he talking about?” I was arrogant. I thought I already knew what to say. But as we started working together I was like, “Holy shit! He's right!” 

You helped me realize that my main goal was to be a family man—that my kids and my wife were the most important things in my life. Looking back, I see now that I’d been too focused on getting what I wanted instead of getting fulfillment in life.

Someone recently asked me, what is one thing that you admire about Bill? I said, “Bill models things that he teaches me.” That is something I had never found. Most people tell you things that they don’t do themselves. Heck, my dad didn’t follow his own advice. 

So anyhow, that's the journey I’ve been on. I certainly think I'm a better thinker and writer.  

Bill: What are some of the ways in which you see yourself being a better thinker?

Vishal: You’ve gotten me to internalize self-questioning. For example: “What is the definition?” “What is the claim (not who’s saying it)?” “What is the argument?” 

The other day I was talking to a friend. Something was off about the way he was approaching the topic, but I couldn’t pinpoint what it was. It took me some time to figure it out: he wasn’t actually interested in evaluating claims. He was instead interested in making judgments. He had an inventory of stereotypes—like conservative versus liberal, or rich versus poor—and would try to slot people into those stereotypes so he could judge them. Rather than listening to what people were saying and understanding their reasoning, he would instead fixate on something—like a word or phrase—that would give him license to stereotype the speaker. That way he could agree or disagree, accept or dismiss. His goal was judgment not understanding. His thinking was simplistic, almost like a teenager hearing one thing and thinking that he figured out the whole world. 

Another example that comes to mind is the progress my business partner and I have been making on our investment project. My partner is sharp. He's able to see all sorts of patterns in the market, but he’s not great at communicating his insights. I’ve been working to formulate our observations as principles that we can apply to specific cases. 

Bill: How would things have been different if you’d had conversations with your investment partner in the past?

Vishal: I would’ve tried just to find some way of agreeing or disagreeing with him. I wouldn’t have tried to understand what he was saying—the kinds of patterns he was seeing. As a result, I might never have gotten to share those insights, and I wouldn’t have had any way of systemizing them. I also wouldn’t have spent any time trying to describe problems. Instead I would’ve assumed that I already understood the problem, and tried to fast-forward to finding a solution. 

One more thing I’ve noticed: I’m able to make better use of expert advice. I’m better at asking the right questions and focusing on the right things. I also have the humility to accept my blind spots. 

Bill: What do you still struggle with?

Vishal: I’m still having a hard time seeking knowledge for its own sake. My current mindset is that I want to learn something so I can use it in some practical application. But I know that Aristotle talks about philosophical contemplation—understanding just for the sake of understanding—as the most satisfying activity humans can engage in. I think you’re a living example of that, but I still struggle with it. Perhaps I just need to be patient. I’ll get there.