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Here's Why the Obstacle is the Way
Jan 5, 2023

Reading time 7 min.

Reality can lead us from self-deception to a richer life.
Ryan Holiday shows us how to apply Stoicism to modern life in The Obstacle is the Way. Late in the book, he summarises his message in a few sentences:

See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.

The Way (or Path)
The underlying point is that life sends us what we need to grow and progress. What confuses most of us is that these developmental gifts from life arrive in unattractive packaging. We get passed over for promotion. Our dream date turns us down. We can’t secure the money needed for our venture. Our relationship hits the rocks.

Teacher and author, Mary O’Malley, delivers a similar message in What’s In the Way Is the Way — our pain and disappointment show us the way forward.

Are these wise authors expressing themselves poetically? Or might they be appealing to a cosmic synchronicity that tracks our progress and lays stepping stones to support our journey? Why or how is it that the obstacle is the way? How does nature lay this path for us?

The Stepping Stones
For me, the message makes most sense through a psychological lens.

  • Modern science shows us that unconscious bias rules much of our decision-making and even our perception.
  • Therapists have helped patients for over a century, exposing repressed and suppressed material we cast into shadow, material that squeezes out in neurotic behaviour.
  • Spiritual sages have long shone light on how our conditioning (inherited traits and early interactions) affects our current experience.

What do these perspectives have in common? The power of the individual and collective unconscious. Our perceptual and cognitive processes sift and distort reality into an image or story before it reaches our conscious awareness. How is this so?

  • Far more information bombards us every second than we can manage. We evolved to use filtering mechanisms that focused on what mattered most to life, death and reproduction.
  • Even dealing with a streamlined data feed, solving every problem from first principles would be painfully slow, so our brains evolved to specialise in shortcuts — rules of thumb that delivered workable solutions most of the time.
  • We were each born into a particular culture in a specific era. The dominant belief systems, social norms, linguistic forms and mythical material shaped how ideas — including ours — formed and propagated in that time and place.
  • Even before we could speak, the emotional environment of the household and family moulded our behaviour, thought and perception into a package that would earn the love and care we needed. That package became our self-definition. We polished this image further to fit in as well as possible with peers as we grew.
  • This self-image and its photo-negative — our shadow — projected further to our assumptions and interpretations of others and even the inanimate world. So our specific inheritance and experience refined evolutionary filters and cultural templates.
  • So was born the storyteller — that voice in our head that narrates life as we live it, the false self interacting with a false world, the self-image that meets our projected image of external reality. It brings its own blind spots, filters, judgements, sensitivities and demands to our experience.

The Lamp
The thing is, there’s only one reality. You know the one — Reality. It includes these images and stories, but it dwarfs them and pays no heed to how the narrator says things should be. The mind’s storyteller paints an ideal world — simple, predictable and comfortable. Meanwhile, reality is wild.

Every self-image is false, as is each story of the world. Just as any computer model of the global economy is a gross simplification of the real thing, every story also misses the mark — blunt-edged and rigid in its attempt to portray reality’s elegant chaos. This is why Lao-Tse said the Tao that can be spoken is not the real Tao.

Today’s world differs greatly from the one in which evolution honed filters and shortcuts in our prehistoric ancestors. We may live in a different culture than the one that shaped us as children, or its norms might have shifted since we were young. Our homes are probably not those we grew up in. Most significantly, we now have greater and more flexible capacities to manage the full range of life experiences. But we’re still operating from the story formed from these outdated components.

Each story misses the mark in its own ways — based on individual conditioning. On some fronts, in certain moments, yours may be a useful approximation of yourself and the world. Mine comes closest in other times, in different dimensions. On the whole, though, every story is out of date, never as dynamic as the world it second-guesses.

What shows where each story conflicts with reality? Reality does! Every moment of our lives, it shows each of us where our self-image and our story are disserving us. These moments of misalignment show up as… obstacles! Experiences we do not want. Events we believe should not be happening. What do they look like?

The better question is, ‘What do they feel like?’ They are the moments of our most intense experiences, the ones that include a powerful sense of discomfort in our bodies. The ones that knock our most advanced cognitive capacities offline. We might replace the word ‘obstacle’ with ‘trigger’ — the things in life that touch a vulnerability and grab us. These unwelcome visitors that defy our preferences are indicators of opportunity. They show us where our self-image and its projection onto the world keep us from dealing with reality as it is.

So you see, life doesn’t deliver obstacles. Life delivers itself in all its variety, and each of us rejects aspects that don’t conform to our personal image and story of how things should be. This is the sense in which ‘the obstacle is the way.’ As children, we unknowingly define what we will view as obstacles throughout our years. Life then highlights them for us so that we can update our definitions as we mature.

Life shows me there is no guarantee others will understand me as I am, no matter how loudly I demand they do. It shows you that even those who love you most will sometimes let you down. Life shows the shopkeeper that she cannot control the behaviour of her staff, suppliers and customers.

Each of us has a path with unique details because every person’s conditioning contains not only evolutionary and cultural components but also household and individual ones. The stones making up each path are shaped and laid by that conditioning. My path is mine. You have yours.

The Blindfold and the Invitation
Reality’s lamp has always illuminated the way. Why have we not followed it?

The storyteller in us doesn’t see this light and its messages as helpful guides but as threats. Their strong physical sensations seem to signal danger, so instead of investigating and heeding them, we flee. In fact, our fear of these intense feelings is so great that we’ll do almost anything to avoid them — disappear deeper into our head-bound narrative or create and act out an external drama to distract us. The short-term distractions are painful in their own right, and they create longer-term issues. Worse still, they don’t insulate us from the unwanted sensations.

This neurotic organisation of distractions makes up a great deal of human experience, and it follows directly from our misinterpretation of fear, anger, confusion and pain. These allies invite us to grow — to become true adults rather than grown-ups acting from a child’s psyche.

We flee them. What might we do instead? Life invites us to experience the anger, including the throbbing it brings to our temples. Experience the confusion, including the knot it ties in our gut. By facing them, we demystify them. When we sit with and through them, we gradually erode our association of these powerful sensations with existential threat.

As we progress, our personal stories and images may adjust, but they won’t disappear. Human life is the experience of story. But life transforms when the story includes awareness of itself as story, when the image includes recognition of itself as image.

This awakening requires a relaxed nervous system, one no longer lurching from threat to threat with each intense experience. Life gives us the material we need to carry out our own experimental training, to relax and to see from a new, more courageous perspective.

The reward is not the reliable satisfaction of our preferences. It is a more intimate experience of life through more robust emotional capabilities. We enter a virtuous cycle, building faith that we can work with whatever life brings.

The way, the path, is the journey toward experiencing life more directly, less through our storyteller’s narration. The stones that make up that path are the aspects of reality that our blind spots, biases, judgements and self-deception have hidden or distorted. We’ve avoided these stones throughout our lives — consciously or not.

But these cobbles populate our present and future as well. Reality shows us the path through the triggered intensity of feeling that accompanies each such stone’s arrival at our feet. Life invites us to step here, not turning around, not skipping to the side, not attempting to soar over on the wings of fantasy. In this step we bear discomfort and learn that we can do so again.

By placing our full weight on each cobble and taking it in our stride, we reclaim and integrate an abandoned piece of ourselves. Walking onward, stone after stone, we finally create the adult we were meant to be.

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