One Quote:

"Superhuman effort isn't worth a damn unless it achieves results." - Ernest Shackleton

You reward yourself for effort—but the world rewards you for results.

Find the leverage in a system. Ensure your superhuman efforts yield superhuman results.

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Sahil Note: Endurance—the incredible story of Shackleton's failed Antarctic voyage—is one of the best books you'll ever read.

One Framework:

Socratic Questioning

The human mind is naturally wired for critical thinking. We're born with an innate curiosity—a desire to understand the world and its nuances and complexities.

The young child who continuously asks “why?” is on this journey of understanding. They ask questions in an effort to dive deeper, think critically, and establish first principles. It works!

Unfortunately, as we get older, we're typically told to stop asking questions. Responses like “Because that’s how we’ve always done it” pile up. Our critical thinking muscles slowly begin to atrophy and we start to rely on base assumptions that we've been told are true.

This is mostly fine when you need quick answers for simple problems. But when faced with complex problems that require non-linear, imaginative solutions, we need a better way.

Socratic Questioning (or the "Socratic Method") is a process of asking and answering questions that stimulate critical thinking to expose and vet underlying assumptions and logic.

Practical Application

To put it into action, follow this general structure:

1. Start with open-ended questions.
2. Propose ideas based on these questions.
3. Probe these ideas with progressive questioning.
4. Repeat 2/3 until the best ideas are developed.

Let's imagine your team at work has encountered a challenge that requires an imaginative solution.

Here's a process of how you might apply Socratic Questioning:

• Start asking questions: What's the problem you are trying to solve? We often waste time and energy trying to solve the "wrong" problem. Identify the “right” problem before you try to solve it.
• Propose your current thinking on the problem: What is your hypothesis? What are the origins of that thinking?
• Open the floor for targeted questioning: Why do you think this? Is the thinking too vague? What is it based upon?
• Challenge the assumptions underlying the original thinking: Why do you believe this to be true? How do you know it’s true? How would you know if you were wrong? Identify the source of beliefs on a problem. Be ruthless in evaluating their integrity and validity.
• Evaluate the evidence used to support the thinking: What concrete evidence do I have? How credible is it? What “hidden evidence” may exist?
• Understand the consequences of being wrong: Can an error be quickly fixed? How costly is this mistake? Always understand the stakes.
• Evaluate potential alternatives: What alternative beliefs or viewpoints might exist? Why might they be superior? Why do others believe them to be true? What do they know that I don’t? Evaluate them on their merits and ask these same fundamental questions about them.
• After zooming in, zoom out: What was my original thinking? Was it correct? If not, where did I err? What conclusions can I draw from the process about systemic errors in my thinking?

As you can see, Socratic Questioning is a methodical process that takes time. For that reason, it shouldn't be used on low-cost, easily-reversible decisions. But when you encounter high stakes decisions in your startup, career, or life, give it a shot. Your decision quality will almost certainly improve.

Sahil Note: I've been thinking about writing a deep-dive on First Principles Thinking and how to leverage Socratic Questioning to execute it. If you'd be interested in seeing this post, reply "Yes!" to this email.

One Tweet:

This was a pretty mesmerizing video that I ended up watching more times than I care to admit.

A few general reactions I had:

• The progression creates a visceral understanding of just how comprehensively the digital world has swallowed the analog. The utility of every analog device on the desk has been slowly, methodically subsumed into the computer.
• The baseline office desk has lost so much of its personality during this period of transformation. All of the externally defining characteristics has been slowly removed. In a world of minimalism and sameness, I wonder what creative ways people will find to maintain their office individuality and continue to stand out.
• The actual desk has yet to be disrupted! In a world of continued technological improvements, being a producer of goods with real physical world utility (sitting, standing, etc.) remains valuable.
• The "arrow of progress" here seems to be that everything is getting smaller and smaller and more self-contained close to our body. Is the next step for the entire computer to be in our body/brain? Pseudo-dystopian concept, but perhaps that's part of our future.

I'm curious: What reactions did you have while watching the clip?

One Article:

​How to Stay Cool When You're Put on the Spot​

We've all had those moments when we get put on the spot at work and feel completely caught off guard. This article sketches out a tactical playbook for managing (and thriving through) them.

The key takeaways I had from reading it:

• Refocus Post-Shock: Your natural "fight or flight" response to the shock of being put on the spot will cause the release of stress hormones. It's important to pause and force at least one deep breath to ease your nerves. Recite some positive affirmation in your head ("I've got this!"). Reframe the moment from being an attack to being an opportunity to learn.
• Don't Make Assumptions: It's easy to go down the rabbit hole of assuming this is a personal attack or an attempt to destroy your credibility. It's (generally) not, so don't burn energy going down that mental path.
• Create a Conversation: Develop a deeper understanding of the questioner's position. Ask thoughtful clarifying questions that give you time to think and create a two-way dialogue that cuts through the tension. Restate the similarities and differences in your relative positions.
• Confident Closing: Provide concrete next steps for getting closer to the truth on the matter. Acknowledge their questions, your initial hypothesis, and the path to improvement.

One final addition from me: Get comfortable saying "I don't know" in a work setting. People are terrified of saying it, but it's such a powerful phrase when stated confidently and alongside a plan to bridge that knowledge gap.

Try this: "I don't know, but I will dig in on [X, Y, or Z] and circle back with the group with an informed perspective by [insert timeline]."

Trust me, it works wonders.

One Podcast:

Andrew Wilkinson: The Knowledge Project

I've been lucky to build a friendship with Andrew Wilkinson over the past year. He is one of those deep thinkers who you can get lost in a conversation with and wonder where the time went.

One of the things I love about him is his willingness to question and fight back against the norms around striving for more, mental health, and entrepreneurial achievement. He covered a lot of that in this great conversation with Shane Parrish.

A few of the most novel takeaways from my notes:

• The Babysitting Razor: When nearing a decision about whether to make an important business hire, ask whether you'd be willing to let this person babysit your kids. It cuts through the noise of whether they are ethical and trustworthy, which is one of the most important traits in a leader.
• Double-Edged Sword of Success: "Most successful people are just an anxiety disorder harnesses for productivity." That line hit...hard.
• Wealth is Not Only Financial: Andrew talks about making all the financial wealth he could ever desire but being completely miserable. This is a topic I am obsessing over. I'm going to be writing more about building more comprehensive wealth in your life (reply "YES!" if you want to see more on this front).

Listen to it on Apple Podcasts or Spotify.

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