Reading a book on how to do something is not always as productive as we think it is. I think that sometimes reading books on how to do something, or how to achieve a goal, is often a direct hindrance to actually doing the thing you are reading about.

For those without experience, a book seems like the most sensible way to learn about doing something. I have some personal experience with this. I loved reading books on finance and economics. It’s what I studied in university and absolutely loved being able to “think big and do all the math.” It made me feel like I was actually doing something! I am solving these textbook problems! Getting good grades! I loved reading Nassim Taleb and repeating shadows of his ideas to my class of non-English speaking teachers and classmates who I thought at the time really thought I was a cool and smart guy!¹

I had a strange mentality where I thought I actually knew what was happening in the world, but this really got knocked down in my first year of my first official “big boy” job. I was an account manager for the European arm of a Taiwanese chip manufacturer. I worked at HQ as the only foreigner who had to report to the local higher-ups regarding what was happening in Europe. At the same time, I was an entry-level salesman where the idea was that I would be mentored to be a big boy salesman.

Obviously, I wanted to impress! I was whipping out spreadsheets and generating estimated future returns based on news articles and reports of metal price fluctuations. I thought I was an analyst. The managers were polite and told me they read all my email reports (sometimes). I thought I was doing my job, but nope—my job was to process orders and just manage the backend of the sale process.

Long story short, I received an email from one of our clients in Spain. It was their CFO with an attached audio recording of him screaming “Me declaro en bancarrota!!”

Oh no… I realised that they are not going to pay us once the OA 30 days deadline hits.

The resolution of this half-a-million USD potential loss was entrusted to me. I was very scared… but I thought that this was my time to shine! I got to work mapping out probable returns and the current risk value of this entire case, calculating the insurance we can claim and future prices of the goods bringing down the market price if they were sold at deep discounts. It was just like the textbooks in business school! Finally, I can prove that I’m smart and that I really know what I am doing!²

I got on a call with the insurance company and explained the situation, laying out the value of the goods, our margin, the shipping costs, and yada yada. I expected them to take the information, provide us with the claim, and deposit the cash in the company’s account by month’s end. You can imagine the shock I felt when the agent explained to me that based on their current analysis, they will not pay out the claim…

“What?? What do you mean?? Is this not why we have insurance?”

See, in the classroom and textbooks, we defined the risk that the insurance might not pay to be something called “Counterparty Risk”. Usually, this Counterparty Risk is there for the sake of simplifying your expected return model. We need to assume sometimes that there is a global financial meltdown and the insurance company has somehow also burned to the ground, leaving them unable to pay.

But what they don’t teach you is the reality of the situation: it’s not the end of the financial world that will stop you from getting your payout. It’s an account manager called John working for a bank on the other side of this insurance claim who just doesn’t want to bother with some extra paperwork before he clocks off.

My point is, I thought I was hot shit, assured management I could get it done, and got slapped in the face with reality real quick. I ended up only getting around $3,500.00 from the insurance claim after we had to send the rep over to the company and have him talk the business into shipping the goods back to some warehouse in Hong Kong.

Reading all these books and doing all these fancy statistics really got me nowhere. In fact, it inflated my ego and might be the reason I was unable to get the full insurance payout. Was I better off knowing these things? I do think knowing this was better than not knowing it, even if my view of reality was skewed… but I think there is something that the classic “nerd” stereotype does get right: we get lost and get proud of being able to intellectualize things that we assume to be reality.³

The Taiwanese and, to a greater extent, the Japanese experience this with their English skills. They are amazing test takers, but they can’t speak a word of English when confronted with a native English speaker. Why? Because they have never spoken a word of English. Their Chinese or Japanese-speaking English teacher has prepared them to get 90+ on the IELTS. And they do! They ace that thing! But then they struggle to order coffee because either due to environmental factors or just plain fear of failure, they are unable to practice the spoken part of the actual language—which is the main reason they started learning the language in the first place.

It’s not that the theory is viewed as having greater importance, but it’s doing seemingly productive things that make you feel like you are confronting the thing that you should be doing, when all you’re doing is hiding behind a spreadsheet or learning more vocabulary.⁴

My intuition tells me that I can save frustration and time by leveraging other people’s experience and supplementing my endeavors with the wisdom and knowledge of the successful people that came before me. Don’t get me wrong; theory has its place and should definitely not be neglected. I know how to ride a bike.⁵ I was reading about inverted pendulums after watching this really cool video and got shown the example of “countersteer,” which works in a similar way to the pendulum effect. I went out and tried it and holy crap! It works! If it was not for my random rabbit hole, I would never have learned about this really useful thing and then ultimately tried it! It’s about both theory and practice timed correctly.

You can write many lovely children’s books on how to ride a bicycle and that will never actually teach the child how to ride a bike. And that’s maybe the point of this whole thing. I went out and tried it, figured it worked, and now I use it everyday. Here is what I did NOT do: I did not linger on the Inverted Pendulum and its Lagrangian equations of motion in an attempt to first perfect the theoretical side of riding a bike.

But this is something we do in other fields every day, and the price we pay is inaction while feeling that we have accomplished something.

Please do not neglect theory; read thoughtfully and carefully. Do your logic exercises. But at the same time, know that it is in service of reality. Don’t stay at home looking at the map. Go climb that mountain!⁶

“The first and most necessary aspect of philosophy is the one that has to do with the application of theories such as ‘Don’t tell lies.’ The second has to do with proofs, such as why one shouldn’t lie. The third confirms and analyzes the proofs by asking what makes this particular argument a proof: what is it to be a proof, what is entailment, incompatibility, truth, falsehood? So the third aspect is necessary because of the second, and the second because of the first, and the one that’s most necessary, and is therefore the one over which we should be spending time, is the first. But we get it all back to front. We linger over the third aspect and put all our efforts into that, while utterly neglecting the first. And the upshot is that we tell lies, while being thoroughly conversant with how to prove that we shouldn’t lie.” — Enchiridion 52