step 51: ambiguity
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Step 51: Ambiguity (optimization pt. 4)

The most obvious problem with optimization is “who (or what) are you optimizing into?”

First you must know yourself, then have a mission with little goals along the way allowing you to hack or increase productivity. But if you are in a rush to gain career capital for survival or to earn freedom, your mission is likely not your own, thus requiring disciplined willpower to pursue. This opens us to problems with subjective truth amidst culturally embedded systems. More problematically, optimization reduces for efficiency, in which case there may be no space left for the messy ambiguity of the human soul.

This is part 4 in a 4 part series on Optimization.

PART 1: Bildung

I recently read two books about career advice: Range by David Epstein and So Good They Can’t Ignore You by Cal Newport.

Range discusses that specialization needs to come later in life. You should be collecting experiences, dig in, learn, then pop up, look around, hop fields towards a compelling interest, and then dig deep again. With lateral thinking and making novel connections between fields, you can become a Rockstar. Supplement your specialization with variety so you don’t get locked into static ways of thinking.

So Good They Can’t Ignore You discusses that you should not follow your passion: passion does not lead to success. Being skilled, like a craftsman, and getting to the frontier of your field, while watching out for career traps, will allow you eventual freedom through skills acquisition.

Both books are answers to how to develop career capital. But in both books you must either focus now or focus later if you want success, which grants you more freedom and happiness to follow your own pursuits.

The classic way to get there was Bildung , a German concept of building yourself for life. The idea was that you could stay focused, work hard, accumulate experience and the world would reward you. But according to Richard Sennett and Robert Jackall, this type of life-long loyal dedication, or being a “good stable person” with skills, no longer works in corporate capitalism.

moral mazes step 27
step33: specter of uselessness

Sennett says it is now about Potential, you must appear to have potential , and that means flexibility to do anything or become anything. This means you are not specialized, but merely appear capable of being molded into specialization.

Our schools now train this: not actual specialization, such as productive skills, but how to pass tests and appear promising. This creates a permanent state of deferral, where your skill is having the appearance of being capable of skills… you pitch yourself as a Swiss-Army knife… but when you actually have to produce/work, you just jump jobs… exit instead of overcoming… or play deceitful politics instead of producing.

Newport thinks that you definitely need to specialize and get some skills: otherwise you are subject to the political whims of these “potential” posers: to earn skills is your only leverage and protection…. and unlike “bildung” (earning these skills over a lifetime) you better get them quick if you want to survive in The Culture of the New Capitalism.

Part 2: Willpower and marshmallows

When a person can’t find a deep sense of meaning, they distract themselves with pleasure.”

Viktor Frankl

This seems true… but let’s also look at the reverse benefits of distraction.

First, in “Range” and “so good they can’t ignore you,” as well “Atomic Habits”, everyone says you need to identify your mission or your passion, find your meaning, figure out who you are… and that’s when you put these amazing self optimizations and productivity systems to work.

The unfortunate chicken-and-egg Paradox here is often until you have been active in the world long enough, or have developed a set of deep skills, and had lots of interactions how do you know your mission?

Until you try you cannot know.

While you are on this path to find meaning, but before you have found a “deep sense of meaning,” how will you avoid ” distracting yourself with pleasure” long enough to find your mission?

The classical answer is Willpower.

Willpower is ridiculously fickle, the Self is an illusion

Based on Research by Daniel Kahneman in the book Noise, the “consistent self” is an illusion: it really is a cloud of possibilities that cannot be accurately predicted. You are a multiplicity of selves with a multitude of desires, enacting a market of choices in your head. Yet, we attempt to project a “consistency of self” that just doesn’t exist.

If you cannot know who you will be moment to moment, context to context, what chance do you have of landing on the version of you with strong willpower?

George Ainslie, as discussed in our earlier podcast, Step 19: Breakdown of Will, researched our psychological mechanisms of willpower, showing them as similar to how we perceive the world: anything close to us is more important and looms larger.

Now, with those notes in the background that disrupt our concept of reliance on willpower and our illusion of the fixed self, let’s consider the infamous “marshmallow experiment” where researchers taunted kids taunted with marshmallows, and if they can resist, researchers and other people predict they will be more successful later in life.

But what really happens here isn’t “delayed gratification” or “having a deep sense of meaning”… the successful kids aren’t staring at the marshmallow and resisting temptation. Given what we know of willpower depleting when you use it, instead the children who were successful at the marshmallow test had a coping strategy: the ability to “reorient focus“. They distract themselves with another game.

The lesson: you cannot turn off desire, but you can redirect it.

Just the Tips

Sonke Ahrens in his book How to Take Smart Notes discusses proven techniques to quit relying so much on willpower, shifting productivity into a system fueled by curiosity and discovery.

Part of being productive without pushing yourself is
1 being clear about your goal (short term) and
2 setting up an external scaffolding that can make success natural.

For instance to be successful in Academia, nothing you do matters unless it is published. Publish or perish.

Niklas Luhmann, the highly prolific sociologist Ahrens writes about, developed a framework called Zettelkasten, which leads (almost naturally) to publishable results of your research. The problem is, to publish a paper the way we were taught, you must become several different selves: the Curious consumer, content scraper, outline structure creator, prose generator, then editor.

But what if we could jot down a few key notes in a way that would instantaneously create an outlined publication without us really trying or having to switch between selves? Then we wouldn’t need to fuel each of those selves, each of those roles, with that ever dwindling supply of willpower? Even better, what if your natural curiosity made working feel like discovery, not drudgery, with each idea prompting more until the publications just flow out of you?

“I never force myself to do anything I don’t feel like. Whenever I’m stuck, I do something else”

Niklas Luhmann

Part 3: Stoics v Epicureans

The stoic vs epicurean: This is Willpower vs. Marshmallows. Zettlekasten is really just a structured marshmallow hunt you set up for yourself.

The stoic admonishes you to change your perspective: through an effort of sympathy and will, you need to recognize alternate scenarios of the world through various mental imaginings.

“That person cut me off in traffic: can I control that situation? No. What if they are a jerk, I can do nothing about that, so I cease to respond.. or what if they are in a hurry to get their kid to the hospital? then considering them a jerk is uncharitable and egoistic.” Or stoics use the momento mori imaginings and visualizations to keep us on the right path: “What if I am dying tomorrow, how should I live today?”

Sure, it’s a great system, but it uses a lot of willpower and mental scaffolding to maintain itself as you move through your day, and it is based on your sympathy. You are playing your actions against your imagined, better self: you are manipulating your emotions with mental judo, and once again, the “self” is very unreliable in terms of consistency.

The other option, an alternative to Stoicism is the much less talked about is Epicureanism: The epicurean does what the kids in the marshmallow experiment would do: reorient desire in another direction. This isn’t toughing it out, or manipulating your own sympathies with guilt, as much as finding external desires around us and re-orienting our focus.

To wrestle with a bad feeling only pins our attention on it, and keeps it still fastened in the mind where is if we act from some better feeling the old bad feeling soon folds its tent… and silently slips away.”

William James

This epicurean re-orientation of desire plays into your animal instincts, allowing the self to be whatever it is… which sounds not at all like self-optimization… it sounds more like self-love.

Part 4: Subject/Object, over-indexing, and ambiguity

a long time ago, from Plato to Kant to Descartes, philosophers have been moralizing about people who could not “think for themselves”

Kant Says the enlightenment is

“man’s emergence from his self-incurred immaturity… a lack of resolution and courage to use one’s own understanding without the guidance of another.”

Immanuel Kant

Then he goes on to call people lazy and cowardly for not holding their own counsel. By combining demeaning terms with “how to be” we have a morality: the ideal of the individual thinking subject, who’s goodness was in proportion to his/her isolated interior thought processes.

A bit later Kierkegaard, then Jean Paul Sartre, get into this notion of Subjective Truth, the lived experience from the individual perspective, as perhaps more important than the Objective Truth, or the exterior world we all share.

That is a gross simplification, of course. But we the people liked this idea: it implies the voices in our head were right all along! Hooray! we are right! And everyone else is right too! But at least now, in our subjective heads we are subjectively free, and they can’t steal our “rightness.”

To combat this Subjective Truth tidal wave, Simone de Beauvoir says the problem with modern society is that the subject and object get over indexed. (Over-indexing means it is measured as performing better than it really does.)

This is fascinating: if we believe that our freedom of inner subjectivity keeps us free: “I can think whatever I want, and you can’t steal that,” then how do we account for the relations of the world around us? What happens if you are a slave, bound to a master who objectifies you? Or you are the objectifier? This Object/Subject distinction sets up binaries, which are often used to form ideologies, but on this podcast I keep speaking of overcoming them.

De Beauvior says To be free is to be radically contingent. That is, to be free is to be fundamentally dependent, not independent. My freedom is bound into this reality, it’s values, and the other people within it.

If you consider an analogy, people sometimes refer to humans as computers, with inputs and outputs optimizing our software and upgrading our Hardware. So, yes, we have some subjectivity, but we also tend to be running on platforms developed by coders in California (or wherever), and they have set a range of options in which we are becoming. In this way our subjectivity is still reliant on a shared external reality, you are not simply free because you say so, or because you overcome so hard.

You might be asking, what does this have to do with Self-Optimization?

What are yourself optimizing into?

The premise of most optimization is to become better, to become more, to achieve your goals… and why would you want to achieve? Curiosity? Maybe, but more than likely it is freedom and validation.

If we are optimizing ourselves to be FREE, it is problematic: you shape yourself to be more useful in a culture or system… you optimize your code, which implies stripping out junk and streamlining…

As Douglas Rushkoff says, to play this optimization game is to auto-tune yourself… to only land on perfect notes. There is nothing off-key, you align yourself completely with a fixed point that was designated and designed by someone else. Rushkoff says there is no soul in that. There is no room left for the singer striving to get to that next note, to revel in the humanness of the soul. (this is from “the Knowledge Project” interview)

There is no space left for ambiguity in optimized code.

De Beauvoir speaks of “freedom as transcendence,” that is a movement towards an open future without fixed possibilities. What if, optimization strips away the openness of your future? You can play the self-optimizing productivity game, feel great and see results, but at least know what you were getting into.

In short: be aware of being too subject, which can lead to solipsistic ego, be aware of being too much a superhero reliant on willpower. Remember: your “freedom” (in a human sense) is not found in a mapped out future, freedom is openness and risk… your 10 year plan is not freedom, it is a path and having a path can reduce anxiety, but beware of slavishly adhering to the path.

Above all, beware as your productivity turns you into a tool for the culture, too much a machine, an object of utility. The more you try for freedom, the more enmeshed in the machine you can become.

If I am gonna be a tool, which I am… a really big tool… I want to be some sort of meta-tool. Somehow staying attached to people and the world while overcoming and moving beyond the binaries of mind/body, subject/object.

That is not optimizing… that is complicating. That is reveling in inefficiency and feeling your way around. It is not optimal at all.

My daily habit:

Belly Button Lint


Ugh… way too many references in this one.

I’ll plug these in later when I have more willpower


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