142 - The casually curious die early at the altar of pragmatism


personal development

It’s a December afternoon. I’m sitting in my living room, my straightened-out legs making a bridge between the couch and the coffee table, with the laptop balanced on it, when the thought occurs to me: I’ve been here before.

I’m reading an email. It has got a party popper, a beach umbrella, and a coconut tree emoji. It’s a happy email. But I’m not really reading anything because my eyes have lost focus. I’m only picking out words—not words strung together in sentences but disjointed words that float up on my laptop screen and settle themselves in thought clouds.

To my left are…



Take a break

To my right are…




Is the email from HR begging me to go on holiday? It’s an unusual request alright but that’s only what it seems on the surface. What’s different and inviting goes deeper. I’ve been here before.

It’s August from earlier in the year. My three-year-old daughter Mayu is sitting on my lap. It’s our first time on a train. We have a side-lower berth, the best kind of seat on a train. Outside, verdant green rushes past. Lulled by the unending longway of lush, Mayu has fallen asleep in my arms, leaving me to wander. I read. Thoughts woven into words about the lens of utility we bring to our every choice. This lens is the water in which we, like the fish, swim. It is fused with our reality. We use it without being aware. Why?

Before I can string another thought, my mind leaps back—

Late 2021. I’m sitting across someone I heard on a podcast, found super interesting, and reached out to. Aditya Sehgal had just left Reckitt after twenty-seven years, as President of the nutrition vertical in China.

I’m at the time working on a smart writing assistant for scientists, bringing up a one-year-old with my wife, and trying to develop a reading habit that would help me level up at work.

‘I read what I feel like,’ Aditya says to me.

‘What do you mean?’

‘I read whatever feels interesting.’


I see a furrowed brow.

‘How do you put to use what you read?’

‘I don’t read with the intention of putting things to use. I just read.’

  1. I’ve gathered a small community that wants to learn to think through decisions better. When I ask the group what they care about, I’m hoping for a collective shout for curiosity. After all, I write a newsletter called Curiosity > Certainty and it’s through the newsletter that I have gotten to know most of them.

What I hear back is more sobering, more practical. Tools to help do things better, frameworks to approach situations better.

Back to that August day by the train window with my daughter on my lap. This is what I’m reading:

_In the utilitarian logic of Silicon Valley, servile work is the only kind of valuable work. Captured as I was inside this city, I used to feel guilty whenever I used my “productive time” on anything other than what could turn a profit. _

I guess people don’t wander much any more. When they do, it is with the firm intention of making that wandering count.

Reading as a means to being more efficient at a job.

Understanding decision-making as a means to have more impact for business.

Taking a break as a means to be more productive at work.

Why would you call any of this wandering? That was what was most striking about that Friday email.

‘Why do we need to disconnect?’ I say out loud. ‘So that we can recharge ourselves. Why unwind? So that we can return energized. It is like taking a break is a means to an end. We take a break so that we can be more productive after.’

I’ve broken my stream of thought. I’ve spoken my mind. Now, my teammates are looking at me from the other side of the screen.

‘I find this email striking, I guess, not because it asks me to rethink my relationship with work by asking me to get away from work. It is interesting because it solidifies that exact relationship, while convinced that it has done the opposite.’

‘I never thought about it like that,’ someone in the virtual room goes.

Why (not) to wander?

A polymath is a person of wide knowledge. Breadth of knowledge comes from variety in interests. A polymath is, therefore, naturally curious.

Robin Hanson, a~~n economist, computer scientist, social scientist, author~~ polymath himself, writes:

Seen as a production rather than a consumption strategy, polymathing is mainly looking for and building on connections one finds between distant intellectual areas. And while I haven’t seen data to confirm it, my personal experience suggests a hypothesis: polymaths peak later in life.


Because our key intellectual strategy of looking for connections between areas should work better as we learn more areas. And I feel like I see this in my own life.


_When I seek concrete examples of things, I have a far larger library to draw on, and I find closer, better examples more easily. And when I ponder a puzzle, I can find many more analogies and kinds of explanations to consider. _

Polymaths bloom late. But blooming late sucks.

Think back to Aditya Sehgal. The man, who read as he pleased, taught me the randomest of things. Make your presentations imperfect in all the insignificant parts so that you invite people to point out those minor mistakes and feel better about themselves and be more participatory. You turn them from combatants to collaborators.

He probably found this principle echoed in disciplines that were otherwise unrelated. He reasoned that if experts across domains all agreed on this one thing, without knowing of the others who believed the same, the idea must have legs.

And it does, it did. Here are two areas I can vouch for.

1️⃣Managing people - Admit to your mistakes and show that you’re vulnerable and you’ll see those around you trust you more and reciprocate.

2️⃣Storytelling - Don’t tell straight-line success stories where you’re the hero through and through. Show your foibles while building stories of your success.

Aditya Sehgal, the curious savant, had spent the last 27 years building his library. Those years taught him that the boundaries around domains that we take so seriously are arbitrary. He was the exception.

Reason #1 to not wander: It is expensive.

Wandering around can be hard to justify. There is no accepted finish line. No patrons who encourage you to wander around at their expense. You would be stopped in your tracks by the first gatekeeper. Few establishments, if any, are evangelists of randomness.

‘You must be familiar with my work–Vitruvian Man and The Last Supper. But of late I’ve been fascinated by nature—I’m splitting my time between studying birds’ wings and how water swirls around rocks.’ said a young Leonardo da Vinci to Francesco del Giocondo, the wealthy Florentine silk merchant.

‘Good for you. How will that help you draw my wife?’

‘I’ve to find myself to find my art.’

‘Then better find out and tell me. Or else I’m giving this one to Michelangelo. He promises a better turnaround time.’

If you’ve an appetite for the new and the different and you like to keep your terrain wide, you’ll be more useful than others at solving, as Robin Hanson says, ‘broad hard-to-classify problems.’ If you understand light and shadow, you’ll be able to produce masterpieces like the Mona Lisa.

By definition, broad hard-to-classify problems tend to be not well-defined or easily commoditized. So, what are you good at exactly?

Reason #2: You will struggle for an elevator pitch.

And that’s just the unkind establishment that keeps asking you for a label. There’s another unsavory aspect for those who believe in play as the best way to learn.

Here’s David Epstein, author of the best-selling book Range, throwing a light on the pursuit of the murky:

…I moved from a traditional media career to a role driven by my personal curiosity. Combine capacious curiosity with not having a manager, and suddenly figuring out what the heck to work on is a massive challenge.

If you’re not used to wandering, wandering can feel like being lost. I used to do this thing where, like serial entrepreneur Mukesh Bansal below, I would come at a topic from different places. A few weeks into learning how to learn, for example, my guilt would be pushing the roof. Curiosity is the luxury of the privileged, I would lament to myself and go back to my weekly to-do list.

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Reason #3: Your lack of discipline will burn you out. The guilt of not producing tangibly will eat you up.

Enough said. Though I wouldn’t count any of these reasons as a deal breaker. The truth I suspect is both murkier and hiding in plain sight.

Our enemy is our almost compulsive tendency to make the next step a step up, and not a step down.

To explain this, let me pull out a mountain-climbing analogy from a 2009 piece by a16z’s Chris Dixon. I believe the analogy has aged well. It is called quite literally ‘Climbing the Wrong Hill’:

A classic problem in computer science is hill climbing. Imagine you are dropped at a random spot on a hilly terrain, where you can only see a few feet in each direction (assume it’s foggy or something). The goal is to get to the highest hill.

Consider the simplest algorithm. At any given moment, take a step in the direction that takes you higher. The risk with this method is if you happen to start near the lower hill, you’ll end up at the top of that lower hill, not the top of the tallest hill.

But you’re curious. You’ll wonder about what it is like at the summit of the highest peak. You’ll look around, meander in a way that hopefully gets you closer to the absolute summit. As you do so, you’ll have to square off the desire to beat a new path with the need to be constantly moving up. Dixon adds:

People tend to systematically overvalue near term over long term rewards. This effect seems to be even stronger in more ambitious people. Their ambition seems to make it hard for them to forgo the nearby upward step.

The more vertical meters you’ve logged on your current hill, the harder it will be for you to give up all that and go all the way back down just so that you can make a fresh try at the highest peak. Oh, the pain of committing yourself to this terrible loss. The fear of never reaching the top. You’re human, after all.

These are the words from author and entrepreneur Kahlil Corazo that incepted a new thought in me on that August day on the train.

In the utilitarian logic of Silicon Valley, servile work is the only kind of valuable work. Captured as I was inside this city, I used to feel guilty whenever I used my “productive time” on anything other than what could turn a profit. This guilt clearly comes from the morality of utility. This partnership of technology and the free market has undoubtedly produced a lot of good. Yet the emptiness I felt despite this abundance shows that my desires are much bigger than what the useful good can fill.

Emptiness is a sticky companion. On the couch or at the table, in the bedroom or boardroom, it tends to not leave your side. It makes you you feel put upon.

Children know how to avoid it altogether. You and I did too. Somewhere along the way, the desire to be practical swallowed the desire to be curious. The fun stopped, life took over, reputation and prestige kept us awake.

We stopped wondering. We stopped wandering. Some, like Bruce Lee, continued.

Bruce Lee learned several martial art forms, which led him to come up with Jeet Kune Do, a ‘hybrid martial arts philosophy drawn from different combat disciplines that is sometimes credited with paving the way for modern mixed martial arts.’ That’s not all. He learned philosophy and liked to philosophize.

If you’ve read a Bruce Lee quote of note, you probably must’ve gone what the heck, at least the first time. That was my reaction too.

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Naval Ravikant is another figure known to ‘combine things you’re not supposed to combine’. He reasons:

…because at some level all humans are broad. We’re all multivariate but we get summarized in pithy ways in our lives. And at some deep level we know that’s not true, right?


Like the model of life that the ancients had—the Greeks, the Romans right—where you would start out and when you’re young you’re just, like, going to school then you’re going to war, then you’re running a business, then you’re supposed to serve in the senate or the government then you become a philosopher there’s sort of this arc to life where you try your hand at everything and as one of my friends says specialization is for insects.

I know what you’re thinking. Of course, Mukesh Bansal, Bruce Lee, and Naval Ravikant are pathologically curious. It is easier for them.

Or maybe you and I have got it all backward. Maybe it is an extreme form of wandering that led these people to the summits they reached.

Naval Ravikant was raised by a single mother who used the neighborhood public library as a day-care center for her young son. She would instruct a pre-teen Ravikant to station himself in the library after school and not come out until it closed. So he ‘read everything until he ran out of things to read.’

Looking ahead, it is impossible to connect the dots. Looking back, it is clear. The difference between the two views is just one thing: curiosity over time.

Chasing curiosity is a long climb. You’ve gotta love the climb above everything else.

Last week, we defined wandering, discussed the perils of wandering, and (still) detailed reasons to wander. We concluded that specialization is for insects and that to be human is to wander and get lost and find ourselves. And that chasing curiosity is a long climb where the journey is the reward. This week, we discuss strategies to be insatiably curious.

1️⃣Start with a big question and follow wherever it leads you

From Yuval Noah Harari, the author of everything-is-everything tomes such as _Sapiens _and Homo Deus:

“My method was really to focus on the most important questions and then allow the questions to just lead me wherever they go. You take a big question, like, for example, why have men dominated women in almost all large scale societies for the last 10,000 years? And you want to understand why.

And it’s important to take a question which is not only big, but it’s also very relevant to my life to make it interesting. Something that really impacts me every day.

And when you start reading and researching about it, the first thing you’ll discover is that you have to cross all kinds of disciplinary borders. This is not a question in biology or psychology or economics or philosophy or history. It’s everything. You can’t understand gender relations if you don’t know about human biology. But if you think, oh, biology has all the answers, you also, you won’t understand much. You also need to take history into account and economics into account and so forth.

So what gives you the structure is the question. I have this big question, and I’m on a quest, following it wherever it leads me.

2️⃣Get and give yourself permission

I’m eighteen, looking for an undergrad discipline to major in. I’m a stranger to myself. Because I don’t have a clue who I am, I look outward. I see a social mirror. It’s impossible to miss. I cannot not help but catch my reflection in it. My reflection isn’t mine—it’s made pixel by pixel from what family and friends and my teachers project onto me. What I see of myself is what everybody thinks of me. That leads me to a choice about how to spend the next four years of my life that is safe by consensus.

This path would probably have led to more sunk costs had I not decided to move away from it at a later stage in life. When I do make that decision, it feels like I am throwing away years of specialization. I’m sure I don’t want to climb the wrong hill. Still, giving up a laid-out path to wander isn’t easy.

By the time I’m twenty nine, I have left a well-paying job and an upward career trajectory, have stripped down any work that paid my bills to the absolute minimum, am living as a paying guest in a tiny flat, and have to empty my checking account to propose to my girlfriend.

This period of my life has been my most fulfilling. Still, I give it up upon its first brush of failure when I cannot get a literary agent to represent me for the book manuscript I have written. I return to the base of the corporate ladder and resume climbing it.

I come back to a decidedly worse version of a life I had left three years ago. Why?

I don’t have permission.

Seven years later, on a winter morning, in the middle of another covid clockdown, I hear Nishant Jain on The Seen and the Unseen podcast. At the time, Jain has left a PhD program on how stroke patients control their limbs for first stand-up and later urban sketching.

What do I hear that morning?

And this idea of permission is very dear to my life, because I feel like I have always been a contrarian who does not seek permission. But even that idea is on the surface, like deep inside, I feel all of us need permission from various forces in our life to do anything. And we seek it from peers, we seek it from people who inspire us, let me do something, tell me I can do something, show me how I can also do something. I saw the stick figure comic and I told myself, you know, I don't know how to draw, but I can also make a webcomic. And I started to make a webcomic. And I started to make a webcomic just like xkcd. I would talk about my life though. But just like him, I would draw three times a week and publish it. And it became a thing. And I got into this idea that I can put my drawings on the internet, which are not very good.

That’s Jain recalling his life before he makes the leap away from what he has agreed to to what he wants. Today, Jain spends his days secretly drawing the world, teaching people to draw, and talking to artists on his podcast.

Just like permission from a role model (xkcd) allows Jain to jump off into a pursuit of curiosity in the face of an aggravating fear (not completing his PhD, losing a future), permission from Jain kills the guilt to chart my own path.

Opposition to your chosen path is not the only reflection you see in the social mirror.

Rhiannon Beaubien worked at Farnam Street for six years, co-authoring the _Great Mental Models _book series. That wasn’t all there was to her. She had a secret. She wrote fiction too, much to people’s chagrin.

I frequently get patronized about writing both fiction and non-fiction. It’ll be harder to sell, I’m told. People won’t know what to do with you, they say. It all may be true.

But I also know that I’m a better writer because I write both. Learning for non-fiction informs plot construction. Developing story arc in fiction helps me maintain reader attention whilst describing history.

What I love about what Beaubien says here is that she doesn’t deny the merits of honing in on a niche. Her goal is different. How many tools do I have as a writer? What can get me more, newer tools? It’s a scorecard she keeps just for herself. That drives her explorations.

In the moment, when you haven’t tasted success or been validated by society’s standards, it may be hard to stand your ground and fly the flag of curiosity. You need a way to look at your reality that is helpful to your cause.

I tell myself that people have strong opposing views because they aren’t sure.

Being right brings a calm reassurance, like you wouldn’t break your head if someone said 2 + 2 = 3. Wanting to be right, on the other hand, brings with it the need to justify, defend, and prove your position. People wanted to prove to Beaubien that sticking to a niche was the best way. They _wanted _to be right, so they spent all this energy in their fight to be right.

3️⃣Let your fooling around be guided by a deep instinct (not utilitarianism or casualness)

‘When reading I’m looking for ideas,’ says Naval Ravikant about his consumption process. ‘When I find something really interesting I’ll reflect on it. I’ll research it. When I’m bored of it I’ll go to another book.’

‘Switch when bored’ may seem like going in circles but it’s not. It is given meaning by reflection. I think of Ravikant’s process as a series of W’s. Scan the surface, dive in, come up for breath, scan the surface, dive in. Do enough dives and you’ll find something new on the ocean bed. Utility is the by-product, not the destination.

The notion of boundary-less knowledge can be sometimes abused by the casual curiosity-seekers.

During my early days of public writing, I once moaned to Aditya Sehgal about how I wasn’t getting feedback on LinkedIn and how that was stifling my growth. He shot back: ‘Then spend your time somewhere you’re more likely to get feedback.’ The casual seeker often confuses feedback with validation.

How to separate casual from genuine? Robin Hanson employs a clarifying strategy.

What about the risk that one will pretend to be a polymath as an excuse to dabble unproductively in many areas? My strategy is to **hold myself to the standards of publishing original insights in each new area **I allow myself to pursue. If I don’t think I could meet that standard, I’ll give the new area a pass.

What does being curious look like?

Two issues ago, I published a piece championing friction. How in meaningful pursuits in life, the inefficiency is the point.

Sometime after, on a weekday run, I tuned in to a conversation between polymath Tyler Cowen and Lazarus Lake, someone who has made a profession out of designing ultramarathons. His most famous creation is ‘Barkley Marathons, an absurdly difficult 100-mile race through the Tennessee wilderness that only 17 people have ever finished in its nearly 30-year existence.’ All of this without GPS.

At one point, Cowen asks Lake about the one skill that holds back participants, a number of whom are special forces people from around the world, the most. Lake says:

I think these days, navigation is a bigger problem than it used to be because people have become dependent upon GPS. If you don’t use part of your brain, it withers. If you’re not accustomed to knowing, in your head, where you are and just listening for a little voice to tell you when to turn next, it’s something of a problem because they don’t get to take GPS.

Incidentally, my piece on meaningful inconveniences (London black cabs and their four-year apprenticeship, minimally invasive heart surgery, Gen Z dating habits) links up with Lake’s specific point. Together, they all roll up to the broader and very interesting question of what it means for us humans to be always looking for convenience.

I’m not suggesting that every random thing you expose yourself to will lead to a connection somewhere down the line, a connection that is practically useful. I’m not even saying that making connections is the ultimate objective of chasing interesting things. I’m only asking you to reconsider the definition of utility. Making connections can be joyful. Doing things because they seem interesting is freeing.

  • Openings: 1) remember reading Patrick Colison's piece on research and wondering what the heck does this guy know.
  1. disconnect, utility
  • Robin Hanson article

  • Aditya Sehgal goal-less reading list

  • Yuval Noah Harrari follow a question

  • Naval Ravikant combinatorial

  • Tyler Cowen's intellectual curiosity

  • my own experiences with decision-making community

  • permission kills guilt

  • multiple frames

  • most jobs are designed for specialists

  • generalists are like children. They have much less to lose than specialists who are adults with responsibility and reputation

-Certain combinations of skills come pre-packaged such that someone skilled at that combination earns a specific label such as a founder or entrepreneur or CEO, without being called a jack of all trades or a generic term such as a polymath.

-this constant nagging feeling about being unproductive en route to satisfying intellectual curiosity (being an eternal student/hobbyist, learning at someone else's expense)

-paradigm shift: maintain your own P/PC balance. Intellectual curiosity is a good night's sleep that readies you for the day ahead.

-permission from role models, and permission to self to choose a response of curiosity in the face of dire stimulus (money, lifestyle, prestige)








Learning how to learn: Ultralearning + The Art of Learning + Check Kindle library

Rhiannon Beaubien on keeping her territory large

Are we literally losing our way?

Why do I quote Robin Hanson so extensively for this piece?

Climbing the wrong hill



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