Today at a Glance:

• An intellectual sparring partner is a friend, colleague, or acquaintance whose combination of background, competency, and personality makes them well-suited to strengthen the quality of your reasoning and decision-making via active, grounded discussion and debate.
• To identify one, look for a combination of a different background from your own, clarity and depth of thinking, and a kind but direct personality.
• Establish structure with regular “sparring sessions”—1 hour on a fixed weekly or monthly cadence, with clear topics and desired outcomes to guide the discussion.

Intellectual Sparring Partners

Over the weekend, I posted a thread on Twitter on the topic of ideas I can’t stop thinking about.

It was intentionally broad—a running list of some of the most interesting concepts, frameworks, paradoxes, and mental models that have been percolating in my mind over the last several months.

If you’ve been following along for a while, by now you’ve realized that my posts are rarely intended to give you “the answer”—they’re intended to make you think. I want to give you the tools, but leave it up to you to create your own maps of how to use them.

If I can spark new curiosity about a topic—and that curiosity leads to active thinking, learning, discussion, and personal or professional growth—I’ve done my job.

One idea from the list—Intellectual Sparring Partners—seemed to spark a lot of interest, discussion, and follow-up questions.

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Interestingly, when my friend Alex Lieberman asked me which of the ideas on the list has had the biggest impact on my life to date, intellectual sparring partners was my answer.

Why?

Well, one intellectual sparring partner—and one “sparring session”—completely changed my life.

So in today’s piece, I’d like to shine a spotlight on this idea:

• What is an Intellectual Sparring Partner?
• The sparring session that changed my life.
• How can you find one?
• The makeup of a great “sparring session”.

With that context in mind, let’s dive right in…

Introduction

I’ve been fortunate to meet and interact with many top performers in my life.

One common trait I’ve observed: they all legitimately enjoy being wrong. They embrace new information that forces them to change their viewpoints—their open mindsets allow them to accumulate and compound knowledge at an accelerated rate.

This innate desire to be wrong—to get closer to the truth—leads them to seek out people who are willing and able to push their thinking in new directions and to greater depths.

These people are their intellectual sparring partners…

Let’s check Sahil’s Dictionary for a definition:

Intellectual Sparring Partner (Noun): A friend, colleague, or acquaintance whose combination of background, competency, and personality makes them well-suited to strengthen the quality of your reasoning and decision-making via active, grounded discussion and debate.

Put simply, an intellectual sparring partner is a person who is willing and able to question, critique, and pressure test your thinking.

Friends come easy—intellectual sparring partners are harder to find, but are incredibly important and valuable.

A Personal Story

To bring this concept to life, I’ll share a quick personal story…

In early 2021, I was completely lost. From the outside looking in, everything was fine—I had built a large following on Twitter, I had a good job, etc. But on the inside, I felt like I was wandering around with a blindfold on.

I had decided to leave my stable job in private equity—and the wonderful group of colleagues that came with it—to pursue something new, but had run into a series of rejections along the way.

In May 2021, at my point of peak uncertainty, I sat down for a meal with Shaan Puri, the host of the My First Million podcast and one of my go-to intellectual sparring partners.

The conversation went something like this:

Shaan: So, tell me how you’re thinking about the next move?

Sahil: Well, at this point, I’m basically thinking there’s a clear Path A and a not so clear Path B. Path A is to join another big investment fund, but one that’s doing early stage investing—the stuff I like thinking about. Path B is less clear, but it’s probably doubling down on all of my personal business, really trying to build that, and probably investing on my own.

Shaan: Ok…so it sounds like you’re choosing between something that sounds really standard (join a fund) and something that sounds really fun and energizing (personal stuff).

Sahil: Well, damn…when you put it that way…you’re right.

In a very quick back and forth, Shaan had completely reframed the decision in my mind in a way that I never would have been able to on my own.

My own biases and baggage—mainly the deep, misguided desire to have an important sounding title or impressive firm name on my resume—were clouding my ability to make a clear, thoughtful decision about what would be the most enjoyable, energy-creating, and profitable path.

His pushback and reframe was critical. From that day forward, I went all in on Path B. Fast forward 12 months and I couldn’t be happier that I did.

Score one for having an intellectual sparring partner…

How to Identify One

Let’s shift to the tactical: how can you identify your intellectual sparring partner?

First off, it’s important to note that there is no such thing as a one-size-fits-all intellectual sparring partner. The person that works for me might not work for you, and vice versa.

Here are a few of the traits to consider in identifying yours:

• Background: Different from your own across a number of vectors. A fundamentally different “map of reality” is ideal.
• Competency: Exhibited clarity and depth of thinking. An analytical mind that is able to deconstruct problems into component parts.
• Personality: Kind (but direct). You want to feel safe with the person and know that they operate from a basic stance of kindness—but that this kindness does not interfere with their willingness to be direct. This is essential.

Start by thinking about the existing relationships in your life. You might find that there are a few candidates in that pool that fulfill the above criteria.

If not, keep looking. This person (or group of people) will play an important role in your life.

There’s no need to stop at one—you might find that having different sparring partners for personal vs. professional matters is useful.

The Sparring Session

Once you’ve identified your intellectual sparring partner (or partners), I would recommend getting into a habit of having regular “sparring sessions” with the person.

A rough set of guidelines for sparring sessions:

• 1 hour session.
• Weekly or monthly cadence.
• 1-3 pre-planned sparring topics. Each person should send the topic with a few bullets on background and framing in advance of the session.
• Clear desired outcomes. Each person should be clear about the desired outcomes from the session.

I find it helpful to have general discussion prompts on each topic. Some of the starter prompts that you might consider:

• Help me steelman my thinking on X.
• Here’s my current thinking on this decision. How am I being an idiot?
• Let’s invert this problem. If this plan fails, what went wrong?

I’ve personally found that this level of structure is helpful in establishing a baseline practice. If you prefer to be more free-flowing, feel free to ignore this section.

Conclusion

To summarize:

• An intellectual sparring partner is a friend, colleague, or acquaintance whose combination of background, competency, and personality makes them well-suited to strengthen the quality of your reasoning and decision-making via active, grounded discussion and debate.
• To identify one, look for a combination of a different background from your own, clarity and depth of thinking, and a kind but direct personality.
• Establish structure with regular “sparring sessions”—1 hour on a fixed weekly or monthly cadence, with clear topics and desired outcomes to guide the discussion.

I would encourage everyone to make a deliberate effort to identify and foster these relationships. Be a great sparring partner for someone else—create value, receive value.

One intellectual sparring partner can change your life. Find yours—cherish them.

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