(11/3/20) getting sneaky good

How do we right-size the learning process in the era of bureaucracy?

What’s up everyone,

I hope this email provides some respite from Election Day anxiety.

There’s a thought that’s been percolating for a while. “Sneaky Good.”

There are some athletes that are Sneaky Good at the game. Roger Federer is a great example. He is a titan in the world of tennis, but I get the sense that I won’t ever fully appreciate what he does that makes him so good.

There are products that are Sneaky Good. Muji, Apple, and Stripe come to mind. Even if I acknowledge how well-considered they are, I still can’t gather how good they are.

Other less-obvious Sneaky Goods (for your late-night rabbit holes): David Silva, Odelia Goldschmidt, Redis, Clojure, Erlang, Metalab, monasteries in Kyoto, Piet Mondrian, Jhumpa Lahiri, Dhafer Youssef.

The Sneaky Good leaves a profound mark on the psyches of those who encounter it. With thousands of subtle, deft touches and tweaks, it distances itself from the rest of the pack. It exits the plane of competition and enters the plane of beauty.

How does one get “sneaky good”? I’m not quite sure on that yet, but I’ll be exploring that idea with you this week.

What I’m Thinking About

I frequently over-plan the doing of the difficult things. I do so because I'd rather not do the hard thing itself. It's scary. More fun to think about the constellation of related things surrounding the actual thing.

Rather than writing code, I'll scheme about how I would write the code. If I plan it all upfront, it'll compile and work perfectly the first time I run it.

Rather than build a new habit, I'll scheme about what great things life has in store for me when I make that change. If I plan it all upfront, I won't have to deal with the painful dips and valleys inherent in any unfamiliar terrain.

A lot of unnecessary bureaucracy sprouts here. I crave certainty, so I develop procedures to make sure nothing unexpected could ever happen.

This pain-avoidant gridlock grows more and more elaborate the more fear I develop about actually “doing the thing.” What if I get it wrong? What if I simply can’t do it, or look stupid trying to do it?

So I conjure up all sorts of guard rails and distractions and narratives to run away from the reality of doing.

The Reality of Doing

Here is the reality of doing: We take some action and we learn that our current understanding is insufficient. Or we do something and actually accomplish what we set out to do.

In hindsight, we see that our journey towards accomplishment necessarily passed through insufficiency. At each discrete step, we commit to an attempt, acutely experience how it wasn't quite right, and use that discord as fuel to try again.

We have to viscerally experience our own inadequacy to adequately accomplish things. Otherwise we end up deluding ourselves that we've made progress.

Put in other words...

Observations + Costly Signals = Learning.

This is the a lightweight process that undergirds almost every productivity system, theory of design thinking, or development methodology.

The pomp and circumstance of an elaborate process takes the eye off the real goal of a process. Which is for learning to become the purpose of the individual and the organization.

So we can momentarily strip away the Double Diamonds, the Sprint Planning, and the Second Brain. We are left with two important triage points in one's learning experience: Observing and Costly Signaling.

Observing: “What is actually going on here?” We directly observe what is happening within us and around us. Study the game tape, apprentice with the pros, shadow the practitioners and the participants.

Costly Signaling: “Do I experience the effects of my decisions?” Through our actions, we signal our commitment to a position. We don’t offload risks and pool them onto others. We directly experience decision effects, and these effects become our teachers.

Carefully notice things. Feed that forward into consequence-bearing signals of action. Clean up the scrapes and bruises and do it all over again.

The better you observe and the better you produce costly signals, the more you will learn.

Every other learning process is merely trying to make these triage points less painful.

Those who observe and signal will produce much higher quality work, much faster and more certainly, even if their actual process works less linearly than those of process junkies.

The pain and joy of costly signals feed forward into future observations. You create a really tight, adaptive, and organic way to work on anything. Your intellect becomes a tool (but not the only tool) that moves you more dynamically and creatively to these triage points. The way you approach your pursuits becomes less bureaucratic.

Doing both of these together hurts because they force us onto the razor's edge of our comfort zones. But in a time of information abundance, what is rare is the courage to act in conditions of uncertainty.

Some Relevant References

Ultralearning - Scott Young. A manual for autodidacts and students of the school for hard knocks.

Designing Design - Kenya Hara. An exploration of mid-century Japanese design and the importance of “emptiness”.

Creative Selection - Ken Kocienda. Inside Apple’s design process, which is driven by frequent demos and relentless prototyping.

Roger Federer as a Religious Experience. A classic essay from the late David Foster Wallace on the majesty of an athlete at the height of his powers.

How Ronaldo Sought Perfection on the Pitch - The Athletic. Tracing Cristiano Ronaldo’s development from supremely-talented-yet-flamboyant youngster to timeless, efficient, and awe-inspiring superstar. Paywalled, but I think your first few reads are free. Also, The Athletic is the only periodical I pay monthly for. They produce incredible sports journalism.

I hope you all have a wonderful week!

Ammar