I used to think awakening was something that happened to you. Like a lightning strike. Or a really good retreat. Or that one conversation at 2 AM that reorganizes everything. You’d go in as one person, something would crack open, and you would come out different. Awakened. Transformed. Done. Cue the sunrise.

I was wrong about this one. Not completely wrong, though, for those moments are real, and they matter. But I had the mechanism backwards. Awakening isn’t an event. It is a direction. And the difference between those two things turns out to be everything.

The Question That Won’t Leave

There is a question that has followed me around for most of my adult life. Sometimes quietly, like a patient companion walking a few steps behind me. Sometimes loudly, like someone who is tired of being ignored, and gets really loud.

Who are you, really?

Not the job. Not the roles. Not the story you have been telling since childhood – the one that started as a coping strategy and gradually became a personality, and then gradually became, in your mind at least, you.

The Enneagram teaches something that stopped me cold the first time I really heard and understood it: we don’t just have a personality. We become identified with it. We mistake the map for the territory. We confuse the adaptive self – the one that learned how to survive, how to be loved, how to get through – with the actual self. And then we spend the rest of our lives wondering why something feels slightly off, slightly thin, slightly “not quite it.”

The unexamined personality is a closed system. It filters out information that doesn’t fit. It reinforces what it already believes. It is, neuroscientifically speaking, a set of grooves worn deep by repetition, and the deeper those grooves, the more invisible they become. We are not driving anymore. We are simply following the ruts.

Which is where the question becomes urgent: Who are you, when you are not being run by the story?

What Awakening Actually Feels Like (Spoiler: Messier Than Advertised)

I want to be honest about something, because I think there is a lot of beautiful-sounding nonsense out there about what awakening looks and feels like. It does not, in my experience, feel primarily like expansion and light and fluffy clouds with floating unicorns. Not at first.

It feels, more often, like noticing. And noticing is uncomfortable, because what you start to notice is how much you haven’t been noticing. The automatic reactions. The loops you have been running for decades. The ways you abandon yourself, or defend yourself, or perform yourself – depending on the space you are in.

I have written elsewhere about a summer where I found myself deep in the grip of my personality – cornered by a renovation project and a cascade of disappointments – and how heavy and airless that rabbit hole became. The personality wasn’t just running the show; it had locked the doors and swallowed the keys. What got me out wasn’t willpower or positive thinking. It was seeing. The moment I could really and clearly see the pattern for what it was – could name it, hold it at arm’s length even briefly, look at it with some flicker of compassion instead of just being inside it – the grip loosened. Just a little. Just enough.

That loosening becomes a step on the journey of awakening.

And here is what I have learned: you can’t force it. You can’t think your way to it. You can’t attend enough workshops about it. You can, however, create the conditions in which it becomes more possible. More likely. More sustainable.

The Problem With Insight (And Why It Keeps Not Working)

Most of us have had The Insight.

The one in the therapist’s office. The one from the book that felt like it was written directly for you. The one during that breathwork session where everything made sense for about forty-five minutes, and then you drove home and got annoyed at a parking situation and were more or less yourself again by Thursday.

This is not a failure of character. This is just how humans work.

Insight without integration is a beautiful, traceless experience. The nervous system doesn’t reorganize around a good idea. It reorganizes around repetition, relationship, embodiment, and time. The old pathways are deep and fast and automatic. The new ones have to be built – slowly, consciously, over and over – until they too become grooved, and what was once effortful becomes natural.

This is why the journey matters more than the destination. This is why staying matters. Not white-knuckling it. Not performing growth. Genuinely, patiently, curiously staying with the inquiry long enough that it stops being a thought you are having and starts being a way you are living.

There are no shortcuts to any place worth going. I keep returning to this mantra, as a strangely comforting orientation. Because it means the path is the point. It means the small daily awakenings – the moment you catch yourself mid-pattern, the moment you choose differently, the moment you let something land in you instead of bouncing off – those aren’t practice for the real thing. Those are the real thing.

What the Body Knows That the Mind Won’t Admit

One of the things I have come to trust more and more is this: awakening is not only a cognitive process. The mind is involved, yes. But the body keeps track of everything. Has been doing it since the beginning of my time, and yours too. The places we brace. The breath we hold. The tension we have been carrying so long we have stopped noticing it as tension and started experiencing it as self. Somatic awareness – learning to actually listen to what the body is communicating – is one of the most direct routes I know to genuine self-knowledge. The body doesn’t lie the way the mind can. It doesn’t rationalize, or spin a convincing narrative, or get defensive. It simply… holds what it holds.

When we start to listen – really listen – something begins to move that thinking alone can’t reach.

The Role of Others (Or: Why a Cave in the Himalayas Is Not the Answer)

There is a romantic image of awakening as a solitary pursuit. The hermit on the mountain. The monk in the cave. The lone seeker, stripped of distraction, arriving at truth through pure inner silence.

I am not saying that is wrong. I have done it myself, cycling and backpacking solo for 9 weeks through Chile and Argentina in 2002. It was impactful and meaningful. It was also incomplete.

We are relational creatures. We develop in relationships. We get stuck in relationships. And, crucially, we often wake up relationships. In the mirror of another person who loves us enough to say the thing. In the friction of community that refuses to let us hide in our usual corners. In the strange alchemy that happens when a group of people commits, together, to witnessing and being witnessed. Margaret Wheatley put it beautifully: “For as long as we have been around as humans… we have sat together and shared experiences… Whatever we did, we did it together.”

This is not a soft, feel-good sentiment. It is a deep recognition of something structurally true about how humans grow. Transformation is not just an inside job. It is also a relational one.

A Beginning, Not An Arrival

Here is where I land, for now, knowing full well that where I land keeps shifting: Awakening is not a state you achieve and then maintain. It is a practice of orientation, sometimes illuminating, sometimes frustrating. A repeated returning. A willingness to notice when you have fallen asleep again – without drama, without self-flagellation – and to turn back toward the light.

Some days this feels sacred and alive and full of meaning. Other days I’d genuinely trade all of it for a clear to-do list, a strong cup of coffee, and not having to look at myself quite so honestly.

Both are true. Both belong. This is what it means to walk the spiritual path with practical shoes.

The question isn’t whether you will fall asleep again. You will. I do. We all do. The question is how quickly you notice, and whether you have built – in and around yourself – the kind of conditions that make waking up a little more possible each time.

That is the work. That is the journey.