Our Fear of Being Free
The Paradox of Choice
Freedom comes at a price. And it’s easy to romanticize that price and forget that freedom can be so overwhelming that you can easily feel trapped by it.
Thomas Jefferson said, “I would rather be exposed to the inconveniences attending too much liberty than those attending too small a degree of it.” And I think most would agree with him.
But while freedom allows individuals to pursue their dreams, make their own decisions, and express themselves authentically, it also exposes them to the complexity and uncertainty of unstructured life. This psychological overwhelm can be traced to the challenges of responsibility, the fear of making wrong choices, and the emotional toll of navigating infinite possibilities.
Imagine, for example, being a new employee in a company and being told, “Don’t worry. You have complete freedom here to figure things out yourself. No one is going to tell you, ‘It must be done this way or that way. ' You get to figure it out on your own!”
We might understandably say (if only to ourselves), “That sounds great and all, but what I’d really like is more structure.” Self-management may be more like riding a bike than driving a train, but if you’re riding a bike on the edge of a canyon, the security of the train tracks becomes an appealing alternative.
And this is one of the core polarities that exists within self-management and leadership: When do we need more freedom, and when do we need more structure?
The Paradox of Choice
At its core, freedom demands responsibility. When individuals are free, they must make decisions and bear the consequences of their choices, good or bad. Psychologist Erich Fromm explored this phenomenon in Escape from Freedom, highlighting how freedom while liberating, can lead to feelings of isolation and anxiety.
Without clear external guidance, individuals may feel unmoored and unsure of how to structure their lives. While this sense of autonomy can be empowering, it can also feel like a heavy burden as people grapple with the pressure of shaping their destiny.
Moreover, freedom often brings with it an overwhelming number of choices. The modern world, abundant in opportunities, amplifies what psychologist Barry Schwartz called “the paradox of choice.” When presented with too many options, like when you’re at a grocery store, and you’re presented with 500 different salad dressings, individuals may experience decision paralysis, heightened anxiety, and a greater likelihood of regret. The fear of making the “wrong” choice can prevent action altogether, as people strive for perfection or worry about future consequences.
Additionally, freedom can introduce existential uncertainty. Without predefined roles or societal scripts, individuals must confront fundamental questions: Who am I? What do I value? What is my purpose? The process of defining one’s identity and goals in a limitless landscape can be daunting, particularly in cultures that prioritize individualism over collective frameworks of support and meaning.
While freedom is a cornerstone of psychological and societal well-being, it is not inherently easy to navigate. The responsibility, abundance of choices, and existential questioning that accompany freedom can leave people feeling overwhelmed. To mitigate this, many turn to self-imposed constraints, external authorities, or supportive communities to create structure and provide a sense of direction.
This interplay between freedom and structure reflects the deep human need for autonomy tempered by the comfort of supportive guidance.
Good and Bad Fear
Obviously, we need a way to think, though, when we have too much freedom and when we have too little. Here is a chart of different situations in which giving up some of your freedom might make sense:
Note: If you are reading this in your email, you may need to click to the article to see the full table.
Note 1: Don’t Forget to Yell for Help.
Note 2: The Only Leadership Theory You Need.
Note 3: How to Sense Your Tensions.
Note 4: Our Inner Gangster.
Note 5: Descriptive vs Prescriptive Expectations.
Conclusion
Freedom has its limits. And sometimes, reliable structures give us the confidence to explore. Rather than feeling limited or constrained, our response to healthy structures is liberation. Not oppression.
One study1 that makes this crystal clear examined how the presence or absence of a fence affects children's exploration behavior in a playground setting. In this study, teachers took preschool children to two different playgrounds during their normal recess time. One playground lacked a fence, while the other was enclosed by a fence. The observations revealed that in the unfenced playground, children tended to stay close to their teacher, showing reluctance to venture far.
Conversely, in the fenced playground, children felt more secure and freely explored the entire area within the boundaries. The study concluded that defined boundaries, such as fences, provide children with a sense of safety, encouraging them to explore their environment more extensively.
True freedom, then, requires a sense of security. And security often requires some limits on our freedoms. So, while freedom is good, it can be overwhelming. If fact, too much freedom actually feels constraining. This is important to remember, especially for those who advocate new ways of working that emphasize increased autonomy.
Rather than assuming that more freedom is the answer, we need to get better at managing the polarity between autonomy and alignment, freedom and structure, in an ongoing and caring way.
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But Don’t Take My Word For It
Too little freedom is captivity, too much freedom is chaos. -Amit Kalantri
Anxiety is the dizziness of freedom. -Søren Kierkegaard
Those who expect to reap the blessings of Freedom, must, like men, undergo the fatigue of supporting it. -Thomas Paine
Man is condemned to be free; because once thrown into the world, he is responsible for everything he does. -Jean-Paul Sartre
People are going to use their freedom badly. That's the way freedom works—but it's better than not having freedom. -Zena Hitz
Freedom is just chaos with better lighting. -Reddit post, a restaurant sign
The average man doesn’t want to be free, he wants to be safe. -H.L. Mencken
https://www.asla.org/awards/2006/studentawards/282.html?utm
 | A guest post by
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All life, all healthy life, is a balancing process of cooperation and competition, of community and individual, of subservience and freedom. Both are necessary for life and health. No rocks are free. No rocks are subservient.
If we are totally subservient, we live a limited, sickly life. If we are totally independent, we are probably lying to ourselves and to others.
We tend to not think of "freedom" as competitive, but freedom is the ability to compete with our communities goals, to create new communities. Humans life in communities of communities of communities of communities. We create, enter, leave, and discard communities without a backward thought in many cases. Some communities, like husband and wife, require a serious commitment, and "freedom" is seen as a failure. Some enforce laws. Others, enforce rules of professional behavior. Others, like a Facebook community of people who love a specific local musical group, can fade away as the subject fades and disappears, without anyone really noticing.
Communities are also individuals, more so as they grow stronger and longer lived. Communities also need to cooperate and to be independent. A community that is not independent, simply doesn't exist. A community that only competes might be a theoretical corporation. In reality, corporations cooperate.
But remember, communities are axholes. Individuals have morals, created and judged by their communities, and moral behaviors, or immoral behaviors, can change depending on the community involved. But communities have no morals, because they have no "peers" comprising a moral community. We tend to enforce community on individual members rather than on the community - a bit of moral blindness.