Home » Reviews » Review: Head in the Clouds: An Invitation to ‘Philosophy’ by Tyler Olsson

Review: Head in the Clouds: An Invitation to ‘Philosophy’ by Tyler Olsson

Michael B. Fielding
Author of The Sailboat Diaries


What books would you bring to a desert island?

This question has been asked on many occasions, yet few people actually run the experiment. The question encourages us to think in unfamiliar ways. In everyday life, our choice in literature might seem a rather mundane dilemma because if I pick up a book and don’t enjoy reading it, I can simply exchange it for another. The desert island scenario thus forces us to imagine a different system of values from which we derive novel evaluations based on the unfamiliar terrain. It’s a fun game to play, but without the first-hand experience of being alone in the middle of nowhere, it can be hard to give much weight to our resolutions.

cover_2I recently lived in a desert for 2 months by myself. It was on a peninsula, as opposed to an island, but the point is that I personally experienced the consequences of limited book choice in that solitary environment. Fortunately for me, I was handed Head in the Clouds: An Invitation to ‘Philosophy’ by my friend, Tyler Olsson, which turned out to be one of best books I could have had in a situation like that.

A cave in Baja California. This is where I was when I was afforded the opportunity to read Head in the Clouds. The conversational prose immediately resonated with me, perhaps because I had no one to talk to, but more likely because it engaged me in imaginary dialogue with philosophers spanning the last couple of millennia. As Olsson has suggested from time to time, philosophy, or philosophical activity, is something like a party had between deep thinkers of all ages, a festival wherein we find ourselves bouncing ideas off one another, testing our notions against evidence and reason. With this imagery in mind, I felt like I was there, discursively dancing, listening, and responding with my friends, while simultaneously engaging Athenians alongside Socrates in ancient Greece. Over the course of this event, I came to appreciate the universality of our drive to live well, something all humans share but few have the courage to pursue. At times my mind raced, trying to synthesize eclectic ideas; at others, I found peace in simply being present with the words.

While Head in the Clouds can certainly be thought of as a book about philosophy, it is more vividly experienced as an artifact of a philosopher’s way-of-being. Olsson’s written words exemplify his own philosophical journey in such a way that astute readers can glean a sense of the general form of this way of life. In effect, the reader is initiated into philosophical space. Like following footprints on a beach, we can learn something about the walker long before we run into them. Our author has been deeply influenced by the thinkers and ideas he has come into contact with, and his reflections on what philosophy is embodies a synthesis of those collected influences. Olsson shares this synthesis with us along with the invitation to join the party, to integrate new perspectives, and pass on our insights to newcomers in turn.

We follow our philosopher down his path by first tracing the roots of the word ‘philosophy’ back to Greece where we also discover the three branches (or moments) of philosophical thought. These moments take place in different settings over the centuries, from the agora, to the church, to the university, where we ultimately find ourselves tangled in self-referential “thinking about thinking” in the present day. Along the way, our guide is careful to skirt disaster while describing certain academic interpretations of the practice, such as definitions of philosophy as the second-order analysis of first-order experience. Olsson ultimately uses this discussion as a foil to set up his own appreciation of how philosophy might be conceived as a lifestyle.

In the second half of the book, we find ourselves back in Greece, this time trapped in a cave watching shadows dance on the wall and wondering if they are real. We begin to talk about knowledge, universals, immortality, virtue, and other ideas that can’t be pinned down with precision. The moral of the story: we cannot attain a true vision for reality unless we figure out the proper way to balance the pull of bodily pleasures with the mind’s desire for understanding. After chatting with Plato, we are swept to India where our vehicle shifts from dialogue to myth. We find the two worlds share a common theme, including a distinction between appearances and truth. We meet Arjuna, a hero-in-the-making, trying to do the right thing when it’s not at all clear what’s right. Struggling alongside him, we are blessed with divine wisdom from Krishna and find peace in knowing our place in the cosmos.

Back to the Greeco-Roman world, with our newfound peace-of-mind, we take notes from the Stoic handbook to liberation: some things are in our control and others not. Simple yet profound, we learn to change our perspective when we cannot change our predicament. Like dogs tied to a moving cart, we can either walk alongside or be dragged, yet herein lies our ultimate freedom! Perhaps counter-intuitively, freedom is enabled by constraint; we cannot play games without rules.

Finally, we are swept eastward once more to witness the dance of the juxtaposed ancient Chinese philosophies of Confucianism and Taoism. Order and chaos incarnate (or so it would seem), and it appears as if we are in the privileged position to change chaos into order at the whim of sheer willpower. Our mental capacities grant us the power to affect the world around us, and the felt responsibility to affect it wisely ensues. Stewards of the earth, we picture ourselves—its future is in our hands!—but the initially felt pressure is short-lived. Our author would caution us not to take the role too seriously. We become anxious only when we try too hard, and our efforts often backfire, creating more problems than we started with. Olsson, following in the tradition of a wise old boy, advises that we instead practice the art of non-action.

Without saying too much or too little, by the end of the journey our guide shows us that we’re already flowing with wisdom. Whether or not you realize it—that is up to you.

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