Authentic freedom through loneliness
Sinking into the de-created self to find more space for love

It’s strange how loneliness can feel like freedom. But that’s the thing about the freedom we strive for constantly. It is lonely.
In a brief respite the other day from the varied and multiple responsibilities I usually carry, I noticed myself feeling these two things simultaneously—freedom…and loneliness. In the next moment, I wondered what was going on. How are these two things connected?
I have resisted writing about loneliness. It is such a ubiquitous topic of newsletters, social media posts, news articles, research, podcasts, influencer advice. What could I possibly add to the noise?
Well, with those two feelings in my being and with a curiosity about their relationship, I thought it was at least worth further investigation.
In order to go beyond the current discourse, I began to look into older texts authored by people who chose to think deeply about loneliness. In the Preface to his 1963 book, The Loneliness of Man, Simon Nash seems to describe a contemporary reality that made me wonder how new all of the causes of and concern over loneliness are: “It is no new discovery that loneliness is a particular problem of our time. The big towns foster it; technological advances give it nourishment; those things which seem to improve human life take their price in the increase of loneliness.”
In Chapter 1, he continues to describe our current moment which, it appears, is many past moments as well but that in our myopic vision we have failed to acknowledge:
However often the words are repeated, it remains true that we live in a highly self-conscious and analytical age. We are constantly reminded of our difficulties and told that we are anxious, lost, and introspective. We are also told on all sides that we live in a fragmented society where there is no common background of belief from which valid symbols can be drawn. It is a society in which home ties and local affiliations are weakened, so that there is more of the physical aloneness which draws out inner loneliness. Work is often impersonal and boring, the service of a big, anonymous corporation with no visible representative to be loved or hated. In two generations we have seen terrible wars and their consequences, a reversion to studied barbarity which we thought the human race had long outgrown. We have seen allies turned into potential enemies, and old enemies wooed for their prosperity. In the midst of it all we stand amazed and question whether any loyalty endures, whether there is anything of which people are not capable in the ways of hatred, vanity, and mutual destruction.
All these things we know; and the worst of it is that we know ourselves to be a part of the situation. Hopelessly involved in the march towards annihilation, we know that this same annihilation is one way of bringing about the individual death which each one of us must meet. The shadow that hovers in its mushroom shape above the world is just one visual symbol of what nobody can escape. It is as important to us, in this our time, as the personification of pestilence and famine were to earlier ages. The forms differ, but that which they bring is the same.
Despite the similarity of the problems he outlines individuals and society facing over fifty years ago, Nash (nor others I read) did not view loneliness to be a disease state. Rather, loneliness is our window into the meaninglessness inherent in human existence. One hundred years prior to Nash, in describing how entrenched soldiers sought all kinds of “busy work” to avoid facing head on the danger in which they existed, Leo Tolstoy touched on how we all seek refuge in something because in the end: “Nothing is trivial and nothing is important, it’s all the same—only to save oneself from it as best one can…only not to see it, that dreadful it.”
Nash suggests that the strategy for dealing with “the tragic loneliness of existence”—that dreadful it—is not to find refuge, not to create refuges for others, not to attempt to fix, solve, distract from, or avoid loneliness, but indeed to sink more deeply into it. What if the prevalence, indeed the epidemic of loneliness, is counterintuitively a sign that humans are inching closer to a fundamental self-awareness and growth that could ultimately bring us all closer together? What if the pervasive loneliness all around us is an instrument of connection and not the annihilator?
Loneliness is an existential recognition that one is alienated from oneself—argues Clark Moustakas in his 1961 work titled Loneliness. It is a signal, rather than a symptom, that there is work to be done before an individual can connect to others authentically. The world that Nash described (and which we still live in only exponentially increased) has created a separation between one’s outward self and an internal feeling of intrinsic value which, Clark explains, needs to be rediscovered since “man has become increasingly competitive, exploitative, status conscious, and suspicious of his neighbor. He seeks group adjustment rather than group solidarity and enters into relations on the basis of formal agreements and contracts rather than trust. In modern life, much social interaction is between surface figures or ghosts rather than real persons.”
We are naive to think that this problem can be solved merely by increasing connection, just as we are mistaken to utilize a medical framing of loneliness as a pathology. The loneliness we turn away from recognizes the “complete absence of concern and love in the world.” When we suggest lonely people increase their social connections, we may only be feeding into the problem. We ask people to connect before they have sat with themselves in aloneness—and not just sitting in it, but mining it for meaning. In this, we offer another escape for loneliness, this essence of the human condition, that each of us needs, first, to recognize “in every fibre of his being” and then, second, to turn bravely towards as it can be the authentic opening point for deeper connection. The paradox is that by doing so—by breaking through the anxious feeling that loneliness dredges up and diving into the depths of existential solitariness—we can shed the pretense of self, just as we must shed the constant distractions we use to keep from knowing this self. Indeed:
There is a power in loneliness, a purity, self-immersion, and depth which is unlike any other experience. Being lonely is such a total, direct, vivid existence, so deeply felt, so startlingly different, that there is no room for any other perception, feeling, or awareness. Loneliness is an organic experience which points to nothing else, is for no other purpose and results in nothing but the realization of itself. Loneliness is not homelessness. There is no departure or exile, the person is fully there, as fully as he ever can be.
Loneliness involves a unique substance of self, a dimension of human life which taps the full resources of the individual. It calls for strength, endurance, and sustenance, enabling a person to reach previously unknown depths and to realize a certain nakedness of inner life.
Being lonely…is an experience of raw sensitivity. It is so entirely pure and complete that there is no room for anything else or anyone else. Being lonely involves a certain pathway, requires a total submersion of self, a letting be of all that is and belongs, a staying or remaining with the situation…until the individual becomes, grows from it, reaches out for others in a deeper, more vital sense.
Loneliness isn't merely a psychological state to be "cured" but rather an ontological structure essential to human being and loneliness anxiety (Moustakas’ term) is “a defense against an unloving world.” A defense. The prevalence of loneliness does not reveal a problem with connection in our world, or at least not primarily so, but rather reveals its emptiness and then further, implicates the human designed structure of that very world in its impersonal, competitive, self-denying constitution.
Thus, loneliness feels simultaneously like suffering and like freedom. In loneliness, we are close to touching meaning, possibility, the mystic perhaps. Loneliness is the opportunity to push the self aside. Being self-absorbed in your own thought is hell, some say, or the worst disease as the narrator in Dostoevsky tells us at the start of Notes from the Underground where he reveals that he “couldn’t become anything—either evil or good, either a villain or an honorable man, either a hero or an insect…[because] an intelligent man of the nineteenth century must be, and is morally obliged to be, fundamentally a being without character; whereas a man with character, a man of action, must be, and is morally obliged to be, a fundamentally limited being.” In The Hills Beyond, Thomas Wolfe identifies the suffering kind of loneliness where: “shameful feelings of inferiority will rise up suddenly to overwhelm us in a poisonous flood of horror, disbelief, and desolation, to sicken and corrupt our health and confidence, to spread pollution at the very root of strong, exultant joy.”
Moustakas's understanding of loneliness anxiety as 'a defense against an unloving world' finds a deeper philosophical foundation in Kierkegaard's work on anxiety and despair. Like Moustakas's lonely individual who must face their isolation to find authentic connection, Kierkegaard saw anxiety (angest) not as a psychological affliction but as the very marker of human potential. For Kierkegaard, anxiety is both an attraction to and a repulsion from the futility of future possibilities. Thus, because of its fundamental relationship to human choice, anxiety is not a psychological state, but a marker on the pathway to human freedom. Perhaps even more material to this conversation, Kierkegaard explained despair (fortvivlelse) as a “not-willing-to-be-onself,” the selfsame self-alienation which Nash and Moustakas illuminated in their work.
Kierkegaard also famously posed a challenge which we still choose to ignore: the question of what is the truth of a thing conveniently ignores the question of what is the meaning of a thing? In the search for truth comes the distorted selfhood which is a pervasive aspect of modern life. Why must truth and distortion be thus related? According to Kierkegaard, truth is subjective. Furthermore, just as you or I can present ourselves in a host of varieties to an other, the self is more than able to relate itself to itself in a multitude of ways—many or most of these mis-relations or misrepresentations. Kierkegaard argued that this misrepresentation of self to self is the cause of despair.
Perhaps or perhaps not. What seems more pivotal is not which part of ourselves is true, but which part of ourselves holds meaning. Similar to the pretense of connection we get from social media, much of our contemporary social system is built on the pretense of self (the pervasive myth of the self-made man, rugged individualism, and the idea that choices can be made independent of social influence are just some). The results of this pretense are that we buy into them or that we do not—and the latter leads to situations like our easy comfort with the commodification of each other through dating apps. These beliefs in individuality—of the self-owned, self-made, self-separate self—are so ingrained in us that when we do find ourselves entirely alone, the true shock—the fear or even despair—is that there isn’t anyone there at all. Truth is a shell surrounding a neverending emptiness.
Whereas some will misinterpret Kierkegaard to argue that true freedom comes from knowing one’s authentic self, what he contended was that true freedom comes from confrontation with inner fears and existential challenges—those very things that come into play when we are deeply alone. Moustakas explains how the person who suffers in loneliness is also
deeply suspicious. Even the slightest criticism hurts him. He often perceives nonexistent deprecation in surface or tangential remarks. Because he feels such grave failure in everything he undertakes, because he constantly strives to raise his level of achievement and win praise and approval and at the same time employs devices and strategies which constantly alienate him from others, eventually he either gives up or responds with aggression to cover up his inner feeling of separation, anxiety, and despair. He is not open enough, flexible enough, expansive enough to attach himself to new persons and find value in new experiences. If he could only surrender to real loneliness, he might emerge as a new person.
The surrender to loneliness can thereby open the door to our truest freedom—not the freedom from responsibility, and certainly not the personal freedom from of which Isaiah Berlin writes in “Two Concepts of Liberty” of which:
Whatever the principle in terms of which the area of non-interference is to be drawn, whether it is that of natural law or natural rights, or of utility or the pronouncements of a categorical imperative, or the sanctity of the social contract, or any other concept with which men have sought to clarify and justify their convictions, liberty in this sense means liberty from; absence of interference beyond the shifting, but always recognizable, frontier. ‘The only freedom which deserves the name is that of pursuing our own good in our own way,’ said the most celebrated of its champions [John Stuart Mill].
In this type of freedom, the width of the space of non-interference corresponds to the extent of my freedom. My freedom is determined by how much (or how little) other human beings prevent me from attaining or achieving something, thus very often leaving me with a self-righteous belief that I am the victim of the law, the state, the elite, or the “corrupt” minority. The positive notion of freedom—freedom to—stands in contrast because it is defined by a desire to be master of my own fate: “I wish, above all, to be conscious of myself as a thinking, willing, active being, bearing responsibility for my choices and able to explain them by references to my own ideas and purposes,” writes Berlin. The problem with this latter notion of freedom, Berlin believed, comes in its divided, zero-sum concept of self wherein there is a self that dominates and a self that is subject to nature and passions such that the “dominant self is then variously identified with reason, with my ‘higher nature’, with the self which calculates and aims at what will satisfy it in the long run, with my ‘real’, or ‘ideal’, or ‘autonomous’ self, or with my self ‘at its best’; which is then contrasted with irrational impulse, uncontrolled desires, my ‘lower’ nature, the pursuit of immediate pleasures, my ‘empirical’ or ‘heteronomous’ self, swept by every gust of desire and passion, needing to be rigidly disciplined if it is ever to rise to the full height of its ‘real’ nature.”
Berlin's distinction between negative and positive liberty illuminates why loneliness feels simultaneously like suffering and freedom. In pursuing freedom from—the removal of external constraints—we often achieve only further isolation. But in facing the anxiety of freedom to—the challenge of authentic self-realization—we must necessarily confront our existential loneliness. This is not the loneliness of isolation but the loneliness of possibility that Kierkegaard recognized as essential to human freedom.
Berlin offers a possible way out of this impossible duality, though he presents it only as an additional problem of the freedom to. The division into ideal self and lower nature can further cleave when the higher self is conceived of as part of a social collective pursuing higher (read moral) goals. The danger of this view comes in the presumptions that can then be made by a particular individual towards society’s other members in that he can genuinely believe he is acting on their behalf in forcing them to do something (through law or structure) that they resist merely because they are not conscious of their own real selves and thus not aware that they actually desire said outcome. Truly this is a danger—this notion that I know what you need best, but you are too ignorant to realize that you want it too—and we have witnessed plenty of it in recent political, cultural, medical and other realms.
Here, though, is where I also see the possibility of a new perspective on both loneliness and freedom, and it turns on the dime of self. Berlin's concepts of freedom from and freedom to still assume a self to be freed, whereas genuine freedom might require the dissolution of this very assumption. Despite Kierkegaard’s older reputation being that of a champion of the isolated self, newer and more nuanced readings of the complete body of his work offer a different vision of self in which
a human being is said to be a synthesis of distinct poles, “of the infinite and the finite, the temporal and the eternal, of freedom and necessity.” But the human self is not just a static synthesis of these poles. Rather, the self has the task of achieving a proper relation or equilibrium between them. As Anthony Rudd puts it, according to Kierkegaard, human "nature is not simply given to [one] as settled and finished. . . . the synthesis of the different factors in a human being is the task of that human being.
So, for Kierkegaard, the self has capacities for self-awareness, self-revision, freedom, and constitutive relations with others, among other things. But these capacities yield a corresponding project, i.e., the task of becoming oneself, or reaching one's telos of eudaimonia, by realizing one's capacities in a way that brings one into right relations with others and causes one to achieve inner integrity.”
This is a project towards selfhood that does not view the self as split into higher and lower natures, nor does it suggest a static “discoverable” self. Instead, the self consists of capacities which can be reached or not through choices, through the freedom to realize these capacities in a relational process based on meaning, not truth.
In the endless search for truth—whether of morality or of a genuine self—we can find only the “ultimate emptiness of a cynical questioning intelligence,” as Sean Illing aptly articulated the cage of self-absorption and self-distraction in a The Gray Area episode titled How to Feel Alive.
Modern discourse about freedom focuses heavily on freedom from (interference, oppression, etc) while potentially neglecting the “positive liberty” Berlin illuminates, this freedom to self-actualize. The irony is that self-actualization must begin in a state of loneliness—anxious or existential—where one is willing to explore our over-association with ego identity and escape the narrowing of human practice to truth and rationality. Yet, there exists a different kind of consciousness—one that moves beyond individual truth-seeking toward collective meaning, pointed to by all the major religions but also emerging in mystical traditions and in what Durkheim called collective effervescence: those shared experiences of music and mass gathering where self is de-created, discarded, pushed aside—which loneliness can be the doorway into…this new relational freedom a counter to Wolfe’s “pollution at the very root of strong exultant joy.” Loneliness can be the catalyst for both individual and collective transformation as it offers an entryway to the freedom of the collective self without the proselytizing morality of Berlin’s divided self, and the freedom to, as the medieval French mystic Marguerite Porete put it, “hew and hack away at oneself in order to make a space large enough for love to enter in.”
In the hope found through loneliness,
Katie


