How hard could it be?

A superpower?

I think that that’s the superpower of an entrepreneur. They don’t know how hard it is, and they only ask themselves how hard can it be? – Jensen Huang on Acquired

So when the big online record stores told me they couldn’t sell my CD directly, I thought, “Ah, screw it. I’ll just set up my own online store. How hard could it be?” – Derek Sivers in Anything You Want

How hard can it be? Topology was founded to solve a problem that is intractably hard. But how hard can it be? The project would not have been founded if we had not asked ourselves this rhetorical question.

How hard can it be? A five-year-old saying this versus a thirty-year-old saying this are entirely different things. A five-year-old basking in reasonable parental protection has not had the baggage of frustrations. A thirty-year-old has usually experienced many let-downs by this point in life. To be able to embrace challenges with enormous uncertainty and go all-in in the endeavor as an adult is a superpower.

… or is it?

I think that’s only a tiny part of the picture.

The treacherous line

The line between ignorance and courage is a treacherous one.

Ignorance is: How hard can it be? I don’t want to actually know yet. I am just enjoying the thrill of accepting a very hard challenge. I identify myself as someone that can do and must do significant things, and by accepting this challenge I reinforce my self-image.

Courage is: How hard can it be? Thinking about it briefly, I can already name a long list of failure modes, another list of resources and skills required unavailable to me or anyone in my circle, and another list of necessary external conditions that are low-probability but I do not have control over. However, I estimate it is possible to overcome all of them. The mere possibility excites me. I want to make it happen and am willing to endure the process.

From the outside, they look very similar. Even from the inside, they can be confused because the mind has a funny way of tricking itself.

Descending and ascending

To be able to descend into details (engineering, science, creative, branding, human, finance) in one moment and ascend back to big picture thinking in the next to cross-examinate is an important skill. It’s quite a rare skill. In scuba diving, descending and ascending too fast is very dangerous. In entrepreneurial pursuit, descending and ascending very fast through the abstraction layers (go from 30,000 feet to 3 feet in a split second) is needed to constantly course-correct in the here and now towards the general direction of a distant future that is desirable.

Curious at a paranoid level

It is helpful to be curious to the point of being paranoid. To have the desire to know, to open black boxes, to question assumptions and common practices.

If I can’t explain something in plain language with a sharpy on a whiteboard, invoking no jargons in the process, I don’t know it yet. Without this practice, it is very easy to fall into a kind of trap: to explain a set of concepts by circularly referencing others in the same set, without actually understanding any individual one. That kind of “knowledge” is merely a cluster of vectors that suspends in vacuum in the knowledge vector space. It is not grounded knowledge. It it not my knowledge yet.

If the strongest reason I can think of behind a strategy is “successful businesses did it before”, my alarm goes off big time. Successful patterns succeeded in the past, potentially in very different circumstances. Our challenge lies in creating an alternate future. If we are creating something new, it is likely that our organizational structure needs to reflect that. That means questioning common business practices, common management practices, common org structures. If we are creating something new and contrarian, there must be common assumptions made by everyone else that are wrong. What are they? People who make such assumptions aren’t stupid at all. Why do they make them? To find out, if I need to devour information at 3 feet altitude I will do that. If I so much as sense an epistemic connection between the intractable problems at hand and a distant discipline, I will go there to study it and talk to their people.

And it’s definitely not about questioning for questioning’s sake. Feeling good about questioning everything is not helpful. We need to be biased toward taking actions especially the vast majority of those whose outcomes are reversible.

How hard can it be?

It may be already rare to ask that question in the face of uncertainty.

It is probably rarer to back such appetite with the stomach.