On Freedomspotting

Of all the seductive ideas in psychology, none is more dangerous than the idea that one is free. Humans have a tendency to jump to conclusions on the matter, on the basis of the flimsiest of evidence. We also believe that freedom is fragile. So humans who do suspect they are free are usually reluctant to advertise the belief. They suspect that to act visibly free is to invite some form of unwelcome authoritarian attention.

This classic exchange in The Dark Knight Rises illustrates how we think about freedom (Daggett is a corrupt executive with designs on Wayne Enterprises and Bane is the super-villain he has allied with, against Batman):

Bane: [to Daggett’s flunkey] Leave us!
John Daggett: No! You stay here, I’m in charge!
Bane: [puts his hand on Daggett’s shoulder] Do you feel in charge?  (flunkey leaves room)
John Daggett: I paid you a small fortune.
Bane: And this gives you power over me?

How does a free person act? Like Bane? Like a Bodhisattva? Like an Ayn Rand caricature? Like a successful entrepreneur with an early-retirement stash? Like a jerk? Like Frederick Douglass in Diary of a Slave when he has his first epiphanies about the nature of freedom in an environment of whippings?

All of the above. Freedom is a set of archetypal patterns of behavior rather than a state of being. Learning to detect these patterns is an interesting pursuit I call freedomspotting. It can be pursued as a hobby, or as a calling by teachers, investors, dictators, revolutionaries and others with a professional interest in either fueling or extinguishing sparks of freedom.

Freedom as Transformation

I’ve been nurturing this dangerous I-am-free belief for quite a while now, and as the strength of the belief has grown, so has my interest in figuring out whether or not I am deluding myself in some elaborate way, a life-long project.

In parallel, I have become increasingly interested in figuring out how free others are. Relationships depend on getting good at this. In selfish utilitarian terms, non-free people are of limited use to you because their limits depend on your imagination. The utility of free people by contrast depends only on their own imagination. The former must borrow against your freedom to act in novel ways.  The latter bring their own capacity for novelty to the party. The imagination of a group is limited by the collective freedom possessed by its members.

A conservative philosophical position is that no one can free or even predictably awaken another. The best we can do is spot freedom where it has already taken root and decide how to engage it.

Freedom has also become an anchor concept in my approach to thinking about business problems. Such problems become much more tractable when framed in terms of the freedom of corporations (or lack thereof) to act in certain ways. Few businesses bother to ask whether they are philosophically free or enslaved in some sense, but the concepts apply just as they do to individual humans.  There are companies trapped in markets or static self-conceptions just as there are humans trapped in lifestyles.

A business problem is almost always a freedom problem (often masquerading as a “scarcity of discretionary resources” problem), and solving it usually involves doing some freedomspotting.

The most useful conclusion I’ve reached so far is this: freedom is a transformation process  with certain characteristic features, rather than a state of being.  A becoming rather than a be-ing as the cliche goes. Humans are free to the degree that their behavior (which may not be visible) at any moment in time manifests these features:

  1. Expansion: The behavior has an expansive element of exponential evolution to it
  2. Growth: The behavior drives continuous structural change towards higher-dimensional self-perceptions
  3. Inscrutability: Thought processes cannot be reliably inferred from visible behaviors, even if they can be predicted
  4. Openness: The behavior can absorb randomness from the environment

There are conventional labels for the first two of these four features. We use a lot of un-words to describe the first feature: unfettered, uninhibited, unleashed, unchained, unbridled. The words imply both a removal of a constraint and the activation and release of stored psychological potential energy.

For the second, we use words like generative. By higher-dimensional, I simply mean “requiring more variables to describe” rather than something mystical. An individual who moves from an “introvert/extrovert” self-perception to a 2×2 self-model based on “introvert/extrovert; thinking/feeling” has gone from one to two dimensions and can explore four instead of two states of being.  A business can similarly go from thinking that it is an early/late adopter of new technologies to thinking in terms of early/late, core business/new business.

The increased dimensionality of being does not imply evolution from a more impoverished (as in “one-dimensional movie character”) to a less impoverished space. It is not really about exploring previously inaccessible new dimensions (though there is some of that). It is primarily about recognizing new dimensions in what was previously regarded as noise, and hidden in subconsciously generated behavior. So within an introvert/extrovert frame, the effects of thinking versus feeling ways of acting would show up as noise. So increasing dimensionality is an awakening of sorts, to the richness in one’s own behavior. Structural change reframes the meaning of the past as much as it frames the potential of the future (the process can also be understood as a reversal of near-degeneracy in a mathematical sense). The future fully inhabits a space that was partially crumpled or curled up as a zone of bounded noise in the past.

The third feature is probably the least recognized, and I don’t know of any common labels. Inscrutability means that the behavior of a more-free person can appear mysterious to a less-free person. A non-free behavior, even if it is something as simple as taking a sip of coffee, is usually transparent to a sufficiently attentive observer. By contrast, the same behavior can be opaque when it is free, because the intentions driving it can be arbitrarily complex, depending on the current dimensionality of the growth process generating it. If the complexity is visible, it appears as illegible noise to an observer with less freedom along the relevant dimensions. This might be ignored (leading to effects such as the Dunning Kruger effect) or cause FUD.

The last element is usually called learning in the most general sense, but while it overlaps somewhat with what we understand as learning, openness is a larger, more basic notion.  The role of randomness or noise is subtle.

Think of the difference between using a bench-press machine versus free weights. The machine constrains a bench press to be a one-dimensional movement (up-down). Free weights create “noise” — random small deviations from the vertical in the other two dimensions — which requires compensation. This forces you to use your muscles in three dimensions rather than one. So one role of noise in learning is to deliberately introduce what engineers call a jitter signal into quiescent dimensions to keep them bounded away from complete degeneracy. Or equivalently, cause leakage from nominally unperturbed dimensions into nominally controlled ones.

This is also a relatively widely understood phenomenon relating to randomness in many domains.

What is not as widely understood is that true randomness forces you to deal with all reachable dimensions. It is possible to be undergoing an increasing-dimensionality transformation and still remain trapped. If it weren’t for true noise, an optimist who only explores positive emotional states could do so with increasing sophistication throughout life, and never encounter negative thoughts. Just like you could count towards infinity and encounter only even numbers, if you started with zero and stuck to using increments of two. Add noise in the form of random integer increments, however, and you cannot avoid odd numbers. Noise leaking across open boundaries prevents you from censoring parts of reality from influencing your behavior. 

The four elements represent a necessary sequence in the progressive evolution of freedom. In other words, a person undergoing visible transformations (for example, a drug addict cleaning up their act in a rehab facility), but with no snowballing exponential behavior, does not manifest increasing freedom. A behavior that manifests the first three elements (for example, athletic striving) represents freedom of a more evolved quality than one that just manifests the first two.

The key point to understand here is that freedom as a behavior transforms the agent doing the behaving. This is why understanding freedom as a state is a bad idea. Freedom as a state implies a stable entity completely modeled by that state, a contradiction in terms.

Example: Freedom in Art

Art is a particularly revealing example domain, since it is generally pursued by people who believe they are free to a degree, and because the behaviors leave highly visible traces. So as an example, consider the following sequence of artists, whose behavior is revealed by their work.

Let’s assume a baseline: an artist who does one kind of artwork extremely well (say realistic pencil portraits), based on a learnable technique, but has no recognizable signature style. Now consider a sequence of increasingly free artists:

  1. An artist whose work exhibits compounding complexity, but in a signature recognizable style
  2. An artist who work seems to evolve through unpredictable stylistic jumps every few years
  3. An artist whose work does not seem to drive a convergence of critical opinion regarding its significance
  4. An artist whose work incorporates recognizably new elements throughout their careers

The baseline artist is not visibly free; he or she may exhibit freedom in other life behaviors, but it is not evident in the art, since it lacks even signs of exponential evolution. The first artist produces the kind of work that could be imitated (for instance) by a simple machine learning algorithm. The second is undergoing some sort of discontinuous personal transformation — a sort of repeated mold-breaking process. The third confounds the critics because no one theory of the artist’s evolution seems to cover the entire evolving body of work. The fourth artist works within an open boundary rather in his/her own head, and the ongoing incorporation of novelty makes their evolution path dependent. 

Central to this progression is the idea of compounding complexity.

Compounding complexity is easy to spot, but hard to define outside of simple mathematical contexts. What I called the three R’s in The Calculus of Grit are a dead giveaway: Rework, Reference (self-), and Releasing (early and often) 

Why is “compounding complexity” the right term for it? Because, like compound interest, the process feeds on its own past, and in doing so, breaks out of its own older molds. The third is the main mechanism by which openness is enabled.

Example: Freedom in Business

I first started thinking about these ideas in the domain of corporations, which humans construct in their own image, but in simplified form.

As with artists, you can establish a hierarchy of increasingly free businesses.

Assume a baseline: a young business that produces one product (say pencils) using a best-in-class modern process, but with no product differentiation. Now consider the following:

  1. A rapidly scaling company that offers an increasing array of differentiated pencils, with an instantly recognizable design
  2. A company that pulls ahead of the competition in pencil design at an accelerating pace, without stumbling
  3. An inimitable company, seemingly in possession of an innovation secret sauce, that regularly surprises competitors
  4. A company that creates and jumps to new markets without going through painful near-death-experiences every time

In the case of businesses, it is useful to think of freedom as the process of discovering new degrees of freedom just as old ones become locked down in mature market balances of power.

The idea is to always stay on an exponential curve of some sort via repeated discovery of exponential breakaway paths. I briefly explored this phenomenon in my post on the Tempo blog, Overtake on the Turn, Overwhelm on the Straightbut I won’t say more about the business version of this.

The point of this example is that  the freedom-as-transformation-process applies to any entity that exhibits agency, so there is nothing ineffably human about this model of freedom.

Frontiers and Freedom

The un- prefix in words we use to describe freedom is revealing. Freedom is a dynamic that becomes active when a restraint is removed. This restraint removal need not be external. It might be an internal epiphany that opens up closed off realms of thought (through recognition of hidden dimensions in one’s own past for instance). Implicit in all the un- words is the idea that the newly free individual will actually notice and be driven by a kind of latent psychological energy that was always there.

The idea of learned helplessness is an interesting illustration of the interplay of internal and external restraints upon action. Even after an external restraint is removed (such as a door being unlocked), the corresponding internal restraint it maps to may persist (preventing us from recognizing that we can walk through the door).

So an act of recognition separates an unrestrained state from unrestrained pattern of behavior. This act of recognition is what converts  an open doorway into a frontier. It is not sufficient (or for that matter, necessary) to consciously recognize that a door is open and that you can walk through it. A kind of creative energy must take possession of your behavior and propel you through that doorway. The real act of recognition lies in noticing that runaway momentum is developing and choosing not to arrest it.

This phenomenology, however, is not enough. It is also present in the start of vicious cycles that lead to self-destruction, cancerous growth patterns, and patterns of irresistible addictive behavior.

What characterizes snowballing freedom is that it must acquire increasing structural complexity (what startup types think of as scaling) in order to sustain itself as it grows. Otherwise, the rapidly increasing volume of energy flows causes the sustaining structures — internal and external —  to unravel. You have to level up to stay in the game, or risk some sort of explosive collapse.

Addictive collapse is the opposite trajectory, where complexity is lost at an accelerating rate, reinforcing the trajectory rather than limiting it.  Think of running down a steep hill and at some point becoming unable to move your legs fast enough, resulting in a Jack-and-Jill tumble.

Freedom Phenomenology

We can say quite a few more interesting things about freedom behaviors. I’ll offer just four by way of example, but you can apply the basic characteristics of the freedom-transformation process to identify, label and parse a much larger universe of freedom phenomenology.

First, the process is strangely not very dependent on initial conditions. Because it compounds in complexity and unleashes progressive structural change, it eventually becomes unmoored from its beginnings. So you may have first discovered freedom through art during a miserable childhood constrained on every other front, but if the process of exploring freedom through art is never restrained, it will eventually leak into every other aspect of life.  Freedom may retain a memory of its origins, but is not constrained by it.

Second, freedom breeds uniqueness. Because of its path-dependent incorporation of novelty in the environment via structural evolution, a free person becomes more unique over time, a living record of a life that never permanently plateaus. This uniqueness may be very visible in the case of an artist and completely invisible in the case of a monk, but in every case, you have a distillation of the essence of a unique path through the material world.

Third, freedom is a leaky, subsuming process. Human lives have external dimensions, not just internal ones. An inner process of compounding and increasing dimensionality that manifests externally must eventually “take over your life” externally as well. So no part of your life, internal or external, can be walled off from the workings of a freedom transformation. The driver of this subsuming leakage is the fourth feature of the freedom process, the feeding-on-noise. This is what causes a sort of fear of freedom. We all like freedom where we are able to handle it, but prefer captivity where we are not yet ready to handle it (or where we think we might never be ready).  So we compartmentalize both internally and externally — create barriers that separate regimes of being with different “noise” levels. So you might work out with free weights for your body, but be attached to the security of a paycheck at work. But to contain the freedom that is taking root for your in the gym, you have to create and strain to maintain a sort of work-life separation.

Fourth, freedom processes are paradoxically about yielding control over your decisions to runaway energy on the one hand, which drives structural evolution through repeated mold-breaking, and to randomness on the other hand, which ensures that the trajectory is never trapped in addiction or aversion loops. So a truly free person has no real decisions to make; he or she becomes a force of nature, driven by the logic of internal energy and external randomness.

Theaters and Non-Freedom

Here’s the thing about freedom: you only need one outlet for behaviors that manifest freedom in order to be free. You do not need to be free in all aspects of your life. You do not even need to be mentally healthy. You can be messed up, paranoid and generally a psychological train-wreck.

But so long as you’ve got one freedom process going, your freedom is the most essential fact about you; the fact that explains the most about you and most determines your future. This is why we have seemingly paradoxical phenomena like jealous, raving artists and paranoid entrepreneurs. Freedom contaminated by screwed-up-ness.

Of course, how long freedom can continue depends on how ready the rest of your life is. Once freedom leaks and expands into unprepared areas of being and becoming, it can cause fatal collapse rather than than expanding growth. But the process does not have to sustain for eternity, only for a human lifetime. So that is a risk well worth taking.

It is tempting to equate freedom with life itself and non-freedom with some form of slow psychological death, but I’ve concluded that this is not true. It is possible to achieve a state of stable stasis, with all freedom frontiers veiled off. When an environment has a behavioral floor that prevents addictive collapse, or a spiral down into extreme degeneracy and death, you can have stable non-freedom. Add some elements of illusion and you can even manufacture certain fragile kinds of life satisfaction.

Such a state of stable and contented non-freedom is what I’ve come to think of as a theater, and theaters are invariably socially constructed. A theater is a subsuming social environment that draws veils over exits without locking them, but locks away some paths to likely destruction. Every comprehensive social order, such as “American consumerized middle-class life,”  is a theater of this sort, though not all theaters are such comprehensive social orders.

Theaters are not the same as prisons. The represent environments of self-domestication rather than external restraint. Where we share fears, we can collaborate in building walls.

Freedom and Collectivism

Theaters are important in the larger scheme of human affairs because individuals cannot help each other become free, but can help each other keep the possibility of freedom alive. If a society keeps its psychologically trapped members from spiraling down, there is always a chance that they will eventually discover a frontier.

I’ll leave an exploration of collective manifestations of freedom to another day. For now, I’ll just say that the normal identification of freedom in a political sense with highly individualist viewpoints is not entirely misguided. It is far easier to conceive of freedom for an individual or an entity like a corporation, with one locus of true free agency, than for a true collective with multiple loci of true free agency (of course, “one locus” here is an approximation for a highly pre-aligned collective, but we’ll let such niceties pass).

Engineering such collectives is possibly the hardest kind of challenge there is, so most of us default to a collectivism-individualism dichotomous trade-off instead, when we fail to rise to the challenge.

If I sometimes come across as an anti-collectivist libertarian in my writing, it is mainly because we live in a society that operates on the default belief that the trade-off cannot be violated.

In other words, I am not a libertarian (a state-of-being self-perception at odds with a becoming account of freedom). I just find it hard to take collectivism (of both Left and Right varieties) seriously because I don’t see them taking their stated problem seriously beyond some wishful thinking about collective freedom magically “emerging” out of isolated individual freedoms.

Freedom has to start at individual loci because it is a bootstrapping problem, but it need not stay there. You cannot take a random collective and attempt to “liberate” it or catalyze a “mass awakening.”  There is a reason freedom narratives, such as the movie version of I, Robot and the recent Planet of the Apes origin story start with a single free entity. It is not actually possible to script a broader freedom transformation that begins nowhere in particular.

Spotting Freedom

To return to my opening question, how do you spot freedom?

Obviously, you should look for a process that is hard to characterize in terms of a state-of-being. But that is not enough. A big confounding problem in freedomspotting is that a high-dimensional trapped state can look free to a lower-dimensional free process. 

This is one of those pernicious mechanisms by which non-freedom perpetuates itself. A young person is impressed by the mature, evolved and complex life of an older person and seeks to emulate him or her. By the time he or she realizes that the model (the word model is revealing, it typically picks out a state of being rather than a structurally evolving process) is a sort of high-dimension frozen idol, it is already too late. They have spent too much time on a non-free path and are themselves trapped.

Going the other way, we are prone to wishful thinking. We see potential, hope and a chance for vicarious living everywhere we see energy more youthful than our own.

The two rules of thumb I have for freedomspotting under these conditions are the following.

First, freedom rarely looks finished. Anything that looks polished, smooth, seamless and complete in any sense of the word is not free. Hidden freedoms never stay completely invisible.

This of course does not mean that anything that does not look polished is free. The presence of rough edges is merely cause for further investigation. Do the rough edges represent ongoing structural growth; the scaffolding of continuous  identity refactoring. Or do they mark collapsed realities and mindlessness?

Second, only freedom can spot freedom. Humans are much better at detecting similarities between patterns than identifying patterns in isolation.  The main reference pattern humans use in spotting freedom is themselves. So to spot freedom, you must maintain your own freedom.  Your own freedom cannot be evaluated via comparison, however, since that would be circular. It must be grounded in isolation.

The second rule of thumb implies that recognition of freedom is usually a mutual matter involving a notion of polarity. Two free individuals recognize each other as fundamentally more aligned than opposed (kindred spirits) or fundamentally more opposed than aligned (evil twins). In extremely polarized cases, you get soul-mate and nemesis effects. Curiously though the length of the journey so far does not matter. A Voldemort can spot a future nemesis in a Harry. There is more to be said here, involving the Jungian notion of shadows, but I’ll leave that trail for you to explore on your own.

By contrast, the free react to the non-free by experiencing a stab of loneliness: the recognition of the fact that the other is not likely to ever recognize you.

So freedom spotting is a matter of staying unfinished yourself via grounded isolation, and looking for mutually acknowledged evil twin and kindred spirit relationships. If you’re lucky you might find a nemesis or a soul-mate. Somebody who completes you the way the Batman completed the Joker.

This post is related to the last installment of the Gervais Principle and various posts on the Tempo blog earlier this year. You might enjoy reading those if you enjoyed this one.

About Venkatesh Rao

Venkat is the founder and editor-in-chief of ribbonfarm. Follow him on Twitter


  1. The bit about “[t]his of course does not mean that anything that does not look polished is free. The presence of rough edges is merely cause for further investigation” makes me think about classical bohemian notions of freedom. Seeking out the rough edges, dark areas and at that point perhaps enjoying the Russian roulette aspect of not knowing whether will find freedom or “collapsed realities and mindlessness” And, in addition, and different from your take, perhaps not caring. Reference Artaud maybe.

    • Interesting. Didn’t think of that. Perhaps it is difficult or impossible to a priori separate the two without engaging it completely. So not caring would be a sort of nihilstic fail-safe gonzo motivation for chasing rough edges.

  2. “Inscrutability means that the behavior of a more-free person can appear mysterious to a less-free person…the same behavior can be opaque when it is free, because the intentions driving it can be arbitrarily complex”

    I’ve experienced this when I begin working with a new group of people. As soon as my behavior becomes opaque, unfree new colleagues react with fear and suspicion. It seems that they assume illegible behavior is subversive or somehow deviant. Because of this reaction, I have learned to initially limit myself to only one visible norm-crossing behavior at a time.

    I’m really pursuing iterative, exploratory learning. I want to experiment with different tools and styles of work. That’s all.

    • It also seems that there are ‘illegibility hats’ that grant the wearer a reprieve from closer scrutiny. The hat signals that the wearer has a socially defined role where illegibility is expected – “Oh, he is an engineer, and I’m baffled by all that math he must do. No wonder his behavior looks odd to me.”

      I imagine that the ‘mad scientist’ archetype is another example of this sort of sanctioned illegibility.

      • Hmm… I’d say a hat that shields you from outside scrutiny also limits your freedom. A hat is a “closed boundary” in the sense of the “open to randomness” feature in this model.

  3. Leaving a comment while in the middle of this article so I don’t forget:

    What I’m seeing in the four criteria of freedom is a lot of concepts that coincide with chaos theory. The trait of inscrutability makes me think of hysteresis: the system may be repeating in quasi-predictable ways, but there are “hidden variables” at work, changing its future trajectory in the phase space. Meanwhile, this seems to mathematically tie in with both “evolving” in some nonlinear way and growing to some higher level of dimensionality. In fact, the “inscrutability” ties in with the dimensionality even more tightly: the dimensionality of the system’s decision-making has outgrown the phase-space its being viewed through.

    As for openness to randomness, that seems to have to do with a system’s ability to learn, which ties into the other three, but I’m not 100% sure how. What I’m noting from all of this is that this kind of “freedom” can be equated to the mathematical properties of organisms.

    There’s also a tie in to OODA here: the overarching “goal” in Boyd’s discourse is not any kind of set goal, but some intrinsic drive towards achieving more degrees of freedom. As if there were some two way street linking the meanings of “growth” and “freedom”. I’ll have to think harder about it.

    • Yes. I was trying to skirt around those specific bunny trails (chaos theory and more generally, the obvious mathematical way to understand this whole post, and OODA). I try to avoid using those frames too much because they tend to get people thinking about the framework rather than the substance under investigation, freedom in this case.

  4. Also noting that the Gollum effect may be the opposite of this process of freedom, with total gollumization possibly being a state where the process of freedom is arrested. This is for mathematical reasons: the Gollum effect reduces the process of living to a Cartesian plane of discrete points in a finite set of dimensions.

    • Yes. Gollumization is journeying towards degeneracy. I don’t think it is an accident that the word “degenerate” is used for social outcastes. Outcastes and long-oppressed underclasses are merely more degenerate than the mainstream.

  5. Venkatesh –
    I really, really enjoyed this piece from you. I found it insightful on a level deeper than many of your former pieces more economically/corporate/business focused which, despite your argument above, I think are themselves powerfully freedom-limiting “illusions”. At least in American society.

    But your insights here are really worth thinking about. Especially the freedom spotting concept of finding and recognizing another, while your resulting argument of “nemesis/soulmate” possibilities made me smile. You go about your approach on this so differently than I would ever frame it and yet I “recognize” the truth of it, from my own life. But for me, there is no way of getting around the necessary interpersonal dynamic to really decide if it is more likely one or the other, and there are complicating emotional/behavioral and social-constrictive unconscious “blind spots” and un-excavated biases that make that so critically true.:-)

    Really liked this piece therefore and also Alexander Boland’s interesting mathematical and Chaos Theory possible expansions. Fun new ways for me to think about these ideas that I have thought about from a fundamentally different approach, all my life.

    But I can see how they might ultimately be complementary, even “joined”, to help overcome the “broken parts” and get a much freer result overall?

    Thanks, Venkatesh. :-)

    • I am still trying to decide whether you are an evil twin or not June.

      • And that I think is the potential for the greatest freedom-opening possibility of all – what we can break free from in our own naturally developed “cages” to truly spot the other correctly, and thus really learn transformatively. :-) The hardest learning of all, I think.

        • I have enjoyed the article as well.

          One short note about a positive idea of collectivity. An example of a shared collective good is language, which is at the same time highly individualized. Unlike Alexander’s chaos theoretic reference, language growth, meta-level reflection, inscrutability and openness to random aggregation in language poses a model of freedom complying to Venkat’s axioms which at the same time drops sensitivity on initial conditions: individually we all started with baby babble or random first-steps when we learned a computer language, mathematics or some natural language at school. Since language as a model is so compelling, one might ask if it is universal in the sense that if one has another model there might be some homomorphism from that model to language?

          • Hmm… interesting speculation there. Language certainly is one of the least restrictive modes of free expression. Interpreted more generally as somewhere higher up on the Chomsky hierarchy, and used to model random other things like a martial artist’s moves or a bird’s flight, your proposition might well be true. A sufficiently expressive language may be able to expand as fast as the freedom of the person using it.

            I wonder if there is “freedom muteness” of sorts (perhaps the frustration of being on the other side of a Dunning-Kruger effect is such muteness) that comes from being unable to express felt freedom in specific situations. It is a different condition from slavery or oppression.

  6. Venkatesh,

    Really enjoyed this, thank you.
    As a practical matter, I’ve found that it can be difficult to express freedom and also engender confidence in professional settings. Freedom is inherently unpredictable, and people committing resources, time, and reputation to you and your efforts can be made uncomfortable by inscrutability, which they often perceive instead as capriciousness. I have found that repressing my expressions of freedom in these exchanges has increased my ability to get commitments of resources (raise money, influence board decisions, etc). Not sure that it is good in the end, since the value I am offering largely springs from my freedom. Eventually, one’s successful track record can take the place of the performance of scrutability, so perhaps from the practical standpoint, the more successful you are, the more free you may allow your behaviors to be.

    I think this may be why so many resource holders (the VCs in start-ups, producers in film making, publishers in writing, etc) seem to be so absent of freedom. They make a career out of getting others (i.e. LPs) to give them responsibility for their money, largely by appearing professionally predictable, pointing to relevant experience, etc. The breakdown is when this class tries to pick winners from among the free.
    Caveat – when the VC is a successful entrepreneur, (success based on their freedom, more than luck), reverse this relationship – they will often be more likely to invest when seeing like freedom, which can’t be faked in the eyes of the free.

    The hardest part of my professional experience has been negotiating these dynamics.

    • Thanks, your experience confirms mine as well. The most “free” rich people I know seem to treat wealth as flows rather than stocks, and are driven partly by curiosity about how the flow can be directed, and what its physics are, rather than anxiety about stocks being raided/stolen.

      Investment driven by freedomspotting, I suspect, will be more likely to select-in potential Steve Jobs types. When freedomspotting becomes a negative test, to select-out, you get more reliable and predictable investments, but ones that are limited by your own imagination as an investor rather than the entrepreneur’s imagination.

      • Agreed. There is a third class of investing going on increasingly, I’ve noticed, which at first look appears freedom-indiferent – roulette investing. A colleague of mine told me recently of an investor they knew who made 500 $50k bets on as many start-ups. No decision making required, ostensibly, but you only get to be one of the 500 if you fit into the “megatrends” the investor feels are taking place (“software eating everything”, “internet of things”, “mass customization”, etc), which circles back to your excellent point that such an investor is limited by their own imagination.

        • Megatrend spotting …

          A short note about that. Just yesterday I was engaged in a brief conversation with some people who would like to use a micropayment system – basically they want to pay for journalistic articles – but don’t trust Paypal after the Wikileaks affair, or Flattr or other Start Ups founded by smart guys. Likewise Google, Facebook or Amazon with their data collection mania. They are not out for spotting freedom but good manners and they get nostalgic about the Deutsche Bundespost – not because their service was excellent but it was under public control and run by people who took that seriously. For them, freedom is not to fall victim to gamblers ( like the VC you mentioned ), corporate sociopaths, optimizers, secret service agencies. They are not scared about terrorism as much as they are about those who pretend to defeat it. They prefer cash and stocks and what they really own – e.g. a book from a printing press, not a right-to-read on an e-book which can eventually be withdrawn because they violate some terms of contract.

          I just mentioned this because it is easy to miss them through the Start Up filter bubble – small capitalists with great ideas who never approach those who actually hold the money.

  7. Foucault comments in his essays on power that “liberty is a practice,” not a fixed thing. Freedom appears to be similar.

  8. Just adding a brief comment while I’m thinking of it; on practicing freedom, I am reminded of James C. Scott’s “anarchist calisthenics,” from Two Cheers for Anarchism.

    See: https://plus.google.com/102162793011751589081/posts/4FrV9RzJtRF

  9. This reminds me of the Gervais articles.

    You have free sociopaths who are acting in ways that are inscrutable to others. You have the clueless who think they are free but really aren’t. And you have the losers, who have chosen to arrest their freedom in some way: Pam with her art, Toby with his atheism, etc.

    There’s much more to say here, but I haven’t the time. Does that make me “unfree”?

  10. Love this topic. I have a few relevant (I think) concepts for you to incorporate/ refute/ mock as you see fit.

    in-joke: an insight one demonstrates as proof of an attained threshold (or level of freedom). Can be in discussion of a koan or Metamorphasis or Being There, etc, or more covertly in response to a “dog whistle”, where the in-joke serves as encoding-resistant pass(not)word. A cheap trick as currency?

    Awareness without understanding of the in-joke often leads to:
    finger looking: About to speak, the Teacher points at the moon, only to see everyone looking at his finger. Also via Alan Watts as *climbing the sign post* (instead of taking the road). The philosopher’s turpentine effect?

    And lastly, inverdoxical: having paradoxical qualities due to inversion at the extremes. Freedom (as told by Venkat) is clearly an inverdox at the gollum edge, but I suspect this holds at the other extreme too. Surely there’s already a word for this, but I don’t know it.

  11. Venkat,
    Do you happen to have kids?

    I am a freelance DevOps architect and a startup founder. My 3rd one, a girl, was born 2 months ago.

    A lot of younger people in the startup world look at having children as an obstacle on their way to entrepreneurial success.

    Most of the people have kids by default.

    I find that despite the heavy financial and time costs,
    having kids made me freer by adding complexity to my world.