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Impossible Dreams and Skillful Means

3 min

Thoughts on the tension between hope and practicality

Effective art bottles up human experience and makes it available on demand. The artist taps into a particular flavor or texture of experience and distills it into their given medium.

As Josef Pieper says in an essay about music: "In this existential depth of the listener, far below the level of expressible judgements, there echoes—in identical immediacy—the same vibration articulated in the audible music."

Frank Sinatra's rendition of "The Impossible Dream" masterfully evokes the mood of inspired determination. The song swells over the following lines:

This is my quest, to follow that star.
No matter how hopeless, no matter how far.
To be willing to give when there's no more to give.
To be willing to die so that honor and justice may live.

Inspired determination is the combination of an uplifting ideal and a strong will to act in service of that ideal despite obstacles and setbacks.

As a mood it provides catalytic energy that evolves our actions in the world.

Apathy, cynicism, nihilism. These stances are endemic in the modern West. [1] We have trouble caring enough about anything to feel what Sinatra is evoking.

Or, increasingly, we care strongly about things, but in a darker, vitriolic way. We have the conviction without the transcendent ideal.

Mature inspired determination is saturated with love.

These lyrics originally come from a musical about the classic novel Don Quixote.

Don Quixote, after reading tales of chivalry, sets out to become a knight errant, traveling the world doing heroic things. As the song captures, Quixote is full of passion and determination to fight the good fight.

However he is mostly a fool and is the comical epitome of the idealist that makes things worse with their lack of wisdom and skill (and contact with reality).

This source material is important, because it is emblematic of the misunderstanding that so many people have today, where they mistake mature inspired determination for the foolishness of Don Quixote. They over-index on the realism and practicality and become pessimistic and plodding.

Naïveté involves a lack of awareness of how systems we want to change actually work. At best this leads to our efforts at change being ineffectual. At worst, it leads to creating more harm and dysfunction in the world as the second and third order consequences of our actions work against our intended outcomes.

Instead, we want the romanticism and audacity of Sinatra's bellowing, tempered by a grounded pragmatism that is concerned with what works. We want impossible dreams and skillful means.

Our media landscape is filled with a pervasive sense that things are bad, getting worse, and that there is not much we can do about it. [2]

It can be vulnerable to state our deeper longings with earnestness. Most of us want to help others. Most of us want love, peace, joy, freedom, justice. Most of us have a tender-heartedness, even if it is obscured by layers of defense.

Even though it can be uncomfortable accessing these parts of us, they are essential if we are to cultivate the mood of inspired determination. Reliable connection to these parts of us also increases the meaningfulness and significance of life.

Know that it is possible to be overwhelmed with love and care for the sacredness of life and to be deeply practical and skillful.


[1] A problem with the postmodern skeptical attitude is that it doesn't allow for sincerity and deep commitment to a transcendent ideal, because according to its logic there are no ultimate truths, only arbitrary social constructions. Its mode is increasingly snark and derision.

[2] This has been true for at least as long as I've been alive. I'm not just referring to contemporary issues. Also, it is of course a generalization, and the opposite is true in some circles.

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