#143 - Strategies to be insatiably curious

Part 2 of 2 on what it means to spend a life wandering

I like to hit the ground running with every issue, yet I also believe I may have something of value for you that needs a moment’s attention. So, would you please check the end of the article for an important announcement? 🙏

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 covers 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.

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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. By this time, Jain has left a PhD program on how stroke patients control their limbs for first stand-up comedy 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 had 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. 

Nishant Jain’s work

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. 

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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 around 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 my mentor 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.

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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. I used the life choices of Christopher Nolan to make a 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.

Lazarus Lake’s observation couldn’t have linked up any better with my piece on friction and meaning (London black cabs and their four-year apprenticeship, minimally invasive heart surgery, Gen Z dating habits). Together, they roll up to the broader and rather interesting question of what it means for humans to be always looking for convenience. You can now take this one question and go wherever it leads you, just like Harari. 

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 for interesting-ness is fun.

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👋Hi, I’m Satyajit. Welcome to my newsletter that picks apart the messiness of decision-making about business, careers, and life.

This coming week I’m doing a masterclass organized by Colabx for emerging leaders on building a champion team. The plan is to break down 3 old habits that hold back team-building and show 3 new ones that are transformative.

Mar 14 (Thursday), 6pm IST, Zoom. You guys are my special tribe. I’m counting on you. You only have to sign up here: https://shorturl.at/dqEU4 📢

🤿Rabbit holes from today: 

Yuval Noah Harari on YouTube

Where I got permission from: Sneaky Artist

Where Sneaky Artist got permission from: xkcd

Sneaky Artist sees the world: podcast

Rhiannon Beaubien on keeping her territory large

The Great Mental Models (non-fiction); Alone among Spies (fiction)

Robin Hanson

Our lost generation without GPS