The late religion scholar and philosopher Alan Watts (1915-1973) observed many of life’s sure foundations that had been taken for granted as dependable and unshakable crumble throughout Western culture. This experience of getting the rug yanked out from under us time and again has filled many hearts with anxiety and left them grasping for a sense of security. But what if this stripping away of dogmatic certainty were a pathway to peace and a more intimate experience with life? In The Wisdom of Insecurity, Alan Watts invites us to embrace insecurity as a way to die to the illusory “I,” and discover new life and awareness awaiting us in the present moment.

We can think of life as a blip of light between two deep darknesses. And when we contemplate this blip of light, we might consider it a cruel joke that our stories end with question marks and incompleteness when we humans are so full of hopes, dreams, yearning, and a hunger for meaning. But the hunger for meaning, the desire to make sense of what is happening in our lives, is like trying to wrap up water in a parcel and mail it to a friend. There’s no good way to do it. How do you contain this chaotic, dynamic liquid inside a package? The water will seep through the paper before you ever tie it up with a bow—let alone send it off.

Yet this temptation to bottle up life always dangles in front of us. We are constantly trying to draw lines around everything in an attempt to make sense of it all. Plenty of geniuses in philosophy, art, literature, economics, and politics have tried to do the same. It’s actually tragic how many of the best minds are ground down to dull futility in their attempts to capture the essence of this or that phenomenon in life. They’re trying to put something as complex as life and experience into an explainable, static package.

You’d think we’d learn. Life appears to be speeding up. New historical discoveries and scientific findings outmode our old assumptions before we even let go of the older assumptions. The packaging we try to put around the raw chaotic experience of life continues to burst in our faces.

This experience of constantly having what we’re sure of debunked has bled into even the most deeply held foundational traditions and religious beliefs. Even among the staunchest believers, Doubt’s chilly fingers still shock and sting our fundamental beliefs. The popularization of scientific exploration has given rise to a tidal wave of skepticism, leading to brilliant discoveries in this world, but also doubts about a world beyond this one. 

Some philosophers and apologists have tried to coax those who waver back into the fold of traditional orthodoxies via intellectual arguments. But these arguments lack any compelling vibrancy. The myths have already been emptied of their power, thanks to the skeptics.

So between skepticism about the reality of anything eternal and unsatisfying arguments that the eternal exists, we are left in an existential pickle: The conundrum fills us with anxiety, driving us to desperately and voraciously pursue whatever pleasure we can find along the way. To ease the frustration, anxiety, and unsettledness that we feel, we pursue distraction and stimulation in our free moments and work jobs that leave us wondering, “What for?”

What are our options? In the face of this anxiety, we could try to create a new myth to replace the old ones, or we could try to live as if the old religious myths were true. Another option is to face down the void, say it’s all meaningless, and hope that science and technology make our passage into the void a little more comfortable.

But what if all of this uncertainty and insecurity were a blessing rather than a curse? Something to find hope in, rather than despair? What if the stripping away of systems and shattering of our reliance on dogma were an opportunity to embrace the eternal in a new way? What if fretfully clinging to our beliefs and symbols has so far prevented us from truly embracing the transcendent? What if insecurity is emptying out the bowl so that it can finally be filled with something? Maybe you’ve never seen the sky before because you’ve been busy painting a glass ceiling blue. A new way of embracing uncertainty could be a help and a relief both to those who neurotically cling to their images of God and to those who neurotically cling to their beliefs that there is no God.

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Religious systems are attempts to point us to Ultimate Reality, but many convince themselves that their religious system is Ultimate Reality itself. What if our calcified systems of belief were the very thing keeping us from experiencing life in its fullness? What if we hold to these systems so vigorously that we miss the opportunity to be held by the things those creeds point to? It’s a lot like sucking the thumb of the hand that points to Truth. Some traditions call this desperate clutching “idolatry.”

While images and symbols and creeds are meant to express truth, they are not a means of controlling or clutching a truth. Chinese, Japanese, and Indian spiritual traditions respect mystery and entertain ambiguity far better than we do in the West. What many Christians miss (and miss out on) is the way Christ embodies comfort and the embrace of insecurity. He leaves the security of heaven and takes on human incarnation. He’s a wandering vagabond moving from town to town, teaching his disciples how to do the same. They are learning to move forward in the face of uncertainty. Jesus doesn’t have a den or a nest like foxes or birds do.

So here is Christ, the God image himself pointing the way to God. And it's only through his destruction that we can get in touch with the Ultimate Reality that he was pointing to. He died to the things that we try to hold on to for security. As he reminds his disciples, “Unless a grain of wheat falls into the ground and dies, it remains alone. But if it dies it brings forth much fruit.”

So it’s only by dying to our need for certainty, for concrete facts, and by acknowledging the limitations of our knowledge that we become available to God, to the infinite, to the absolute. As hungry as we are to possess the mysteries of the universe, the power of these mysteries comes only when we let go of the impulse to possess it. For atheists and the religious alike, the temptation is to shed openness to reality and harden our posture into dogmatic stances. But in doing so, we close ourselves off to mystery and to wonder, and we can’t see beyond what we think we already know. Without meaning to, we’ve imposed a ceiling on our imagination.

We manage to get nowhere faster and faster when we try to look for security and permanence in a world that never ceases to be in flux. We end up fighting ourselves, like the snake that tries to eat its tail. As long as we fight against the way things are, the parts inside us will fight each other.

As long as we try to change by attempting to freeze and tinker with everything in our lives, we will never understand change. Life is something we flow with— not something we can pick apart like a mechanic in an auto shop. Instead of resisting change, we understand it better when we jump into it and learn how to work with it, to dance with it.

As we’ve discussed above, religions make a fatal flaw when they try to figure out life through fixation and obsession, when they try to distill everything down to a point of doctrine. For whether we use religious language or not, the idea that we can make meaning of life by shoehorning our experiences into a list of immutable laws and boxes means missing out on the ebb and flow of life itself.

We are really quick to forget that words and language we use are just conventions. These conventions make life manageable, but they don’t make life meaningful. The word water is a more efficient way of communicating a concept than dragging someone to a river and pointing, but there’s also no substitute for the experience of bracing cold water rushing over your legs. Conventions help us move through life efficiently, but when we take conventions too literally or too seriously, they can turn rigid and close us off from the deeper meaning beneath the conventions.

Part of our confusion comes from believing that by defining something we have truly understood it. We overestimate the power of words. Intellectuals aren’t the only ones who do this. They merely play out an extreme version of a process that all of us engage in—believing that conscious thinking and articulation capture the heart of something. We delude ourselves when we think this.

Words help us to define ourselves in the world around us, but that doesn’t mean we understand ourselves or the world around us. Moreover, by defining ourselves with words, we cut ourselves off from that flow of life. We remove ourselves with our words; we make ourselves static and separate.

But life is constant movement that we attempt to freeze through thought. That’s a lot like trying to pinpoint the exact location of a train speeding to the next station: As soon as you finish saying the train is “here,” it’s no longer there. Paradoxically, we will open ourselves to more of life when we stop overestimating the ability of words and language to capture it. As soon as we try to make life intelligible through our words, we end up with something other than life.

It is a grand paradox that God, the eternal Word, cannot be adequately expressed through words. And every spiritual tradition recognizes that we must surrender the “I”—the part of us that insists on knowing and defining itself—if we ever hope to lose the feeling of isolation and separateness. When we begin to admit, “I do not know” and “I cannot make sense of this,” visions of God and the infinite begin, too. As soon as you try to name God, and think your words can capture the eternal, you end up with something else.

We’ve discussed problems with trying to capture life with words, and that we run into the same problem when we try to capture God with words. It's like trying to capture wind in a box: the moment you do the breeze is gone, the mystery unravels.

Still we insist on looking to God for wisdom. The problem is not that ultimate reality gives us no wisdom, but us looking for explicit knowledge, advice, and facts to give us a sense of direction. From the indescribable, mysterious source of life, we expect clear, definable instruction.

There’s a tremendous amount of wisdom to be found in the body. Think about it: Your body never needed written or spoken instructions on how to digest food, fight disease, or pump blood through your body. These miraculous and complicated processes are performed instinctually. No matter how much instruction or how many books you read, it does nothing to aid the body’s instinctual know-how. That know-how can’t be replicated through written or oral instructions.

The truth is that the wisdom we rely on most is instinctual rather than explicit. The more explicit the instructions we receive, the more removed they are from the way we actually go about life. It seems the more we try to calculate and create gadgets and techniques to solve problems, the more we mess things up. Conscious thinking can only get us so far, and we’ve deprived the deep, unconscious intuitions of any say in our lives.

We are split into “I” and “me,” where “I” is the conscious self that stands outside of life and experience and attempts to explain and understand it. It also incessantly critiques the “me,” that part of us that experiences life as it is. “Me” takes a dip in the river and lets the river flow over it, and “I” makes judgments of how cold it is and how silly it is that you got yourself all wet. When we split these parts and they are not cooperating, the “I” usually rules us, and keeps us critiquing and analyzing experiences without living them. Some call this way of operating “European dissociation,” where we split brain and body, mind and nature, thought and experience.

So what’s the solution? This is the question that springs from most people’s lips, but it also reflects that we failed to really understand the problem. We assume we can, by some explicitly stated direction or technique, solve the conundrum. But no matter how you thrash your arms up and down or side to side in the dark, you don’t get rid of the darkness. A light has to be switched on.

By “light” we mean awareness. We mean a way of attending to the world in which we experience things in the present moment, while also resisting the temptation to name everything we’re experiencing and put it in boxes. Can you observe life as it is, let it “be” without judging it?

What are we looking for in the moments when we judge and define life and our experiences? We’re looking for security, a type deeper than just physical security. It’s a spiritual, psychological, and existential security that we want even underneath material comforts. We are trying to guard ourselves, to fortify the “I” which has become isolated and lonely by separating itself from life. Hunting for security in a universe that is fundamentally impermanent is a hard ask. Paradoxically, hungering for security and the feeling of deep insecurity are one in the same. When you hold your breath you cut yourself off from breath. If we could learn to stop hungering for security, we would not experience the feeling of insecurity. We would be able to take another breath instead of holding on the last one.

This discussion brings us to the subject of worry. Worry is very much bound up in our hunger for security. We know at some superficial level that worrying does us no good, and yet we compulsively do it. Simply reminding ourselves or having other people remind us not to worry does little to assuage our worry or prevent us from going right back into a state of worry.

Demonizing the desire for safety doesn’t help much either. What will help us more is understanding that there is no safety in isolation as we presume. Uncertainty and insecurity are always with us. If we manage to let go of the idea of an internal continuous self, then the compulsion to grasp for security to protect it will slowly diminish. There is no “I” that we need to save.

And as we let go of this hunger and compulsion to save ourselves, we slowly begin to experience life in the moment as it is. In other words, we have space freed up to become aware. We can enjoy what is in our lives instead of anxiously turning every experience, person, and object in our lives into an anxiety-mitigation tool.

Awareness is full immersion in the present moment, a deep attending to an experience right in front of you. To understand things means to not be divided within yourself, with one foot in the experience and the other part separate from it picking it apart. The moment you tell yourself, “I am listening to music right now,” you are no longer listening to music. The moment you stop laughing at a joke and start analyzing its structure, the magic of the humor dies. To say “I’m afraid,” or “I’m full of joy,” or “I’m excited” takes you out of the immediacy of the moment. But to simply be with yourself and your experiences without labeling them allows you to gain awareness. You can finally stop thrashing your arms around in the dark, hoping it will chase the night away, and you can begin to notice the light appearing on the horizon.  

These insights are just an introduction. If you're ready to dive deeper, pick up a copy of The Wisdom of Insecurity here. And since we get a commission on every sale, your purchase will help keep this newsletter free.