I am walking along the familiar path in the old-growth forest. I come to the point in the forest where the Queen of the Damned scorched the trees and everything living; there is nothing but charred stumps and ash on the ground. All that is left of the wooden signpost is a charred stump that is no more than six inches tall.

I start digging, and the ground almost immediately opens to the dark, deep cavern from my first Active Imagination session. I look around, holding a rope in my hand, wondering what I could tie it to so that I can lower myself down. Without warning, I find myself jumping into the abyss, falling at least forty feet before I land on the ground. My right knee is injured, and I cannot stand. I break a glow-stick and begin crawling along the cavern’s floor. A massive, angry badger comes into view, hisses at me, and continues on its way. I decide to start digging by hand using a trowel. After a few minutes, I wonder how long it will take me to make any significant progress and whether I should give up altogether.

To my right, an animated skeleton appears with a shovel. I feel uneasy, but do not panic. Behind me, I hear a voice, “Need a hand?” I look behind me and see Eliot from The Magicians. He helps me to my feet, and we watch the animated skeleton dig the hole for us. “He’s handy for when you don’t want to break a sweat,” he tells me. I struggle to stand, and Eliot says, “Oh, right. Let me fix that for you.” I wonder how good his healing magic is, but I figure if he can animate a skeleton, then healing a damaged knee shouldn’t be difficult. He moves his hands in the typical ‘Magicians’ manner, and I find myself screaming in pain as the bones repair themselves. Once repaired, the pain is gone, and Eliot suggests that we continue walking.

“What about the hole?” I ask him.

“What about it? I have something better,” he replies.

He waves his left hand, and a flame appears in his palm. He holds it in front of him to light the way. We come to a wall in the cavern, and Eliot runs his right hand against the wall, feeling for something. He whispers an incantation, and the wall opens. “Speak, friend, and enter,” I think to myself.

We step through the opening and find ourselves in a sterile white room with bookshelves and books as far as the eye can see.

“All the knowledge of humanity,” Eliot declares.

I look around, taking it all in, when Eliot asks, “Do you know what knowledge is?”

“Power,” I reply.

“Power. Yes. But what type of power?”

I pause. It occurs to me that I haven’t ever given much thought to this before. Isn’t power just power?

He continues, “Inside all these books is knowledge that has been built upon the knowledge of others. It is creative work. It is imaginative work. Without creation and imagination, there is no true power. What good is all the knowledge of humanity if you cannot imagine what you’d do with it?”

He hands me an old leather book, and as I open it, he transfigures into a bat and flies away. “Odd,” I think, as I open the book. I look at the pages, and they appear to be old, yet well preserved. There is a faint glow coming from the center of the book, and I find myself being pulled inside of it.

I am falling, like Alice falling into Wonderland, but words and letters surround me as I fall. I reach the ground and am surrounded by a yellow-ish mist, like the color of aged paper.

I look around and yell, “Hello?” and the mist parts. “Hello!” I yell again, and the mist parts more, as if creating a pathway. “I am looking for the Self!” I cry out. The path is cut through the mist for a significant distance, and I step forward. As I do, the letters and the words from above fall around me, clanging as they hit the ground as if made of metal. I run along the path, words and letters crashing around me, while I continually shout, “I am looking for the Self!” A letter falls immediately in front of me, and I trip on it, falling face-first onto the ground. I sink into the ground and fall up into a black room.

“Original sin,” I hear a voice say.

“I am looking for the Self,” I reply.

The room zooms at an immense speed, and I am sitting on the edge of a mechanical device that has various cogs and a rotating crest of rings, almost like the Basileus’s Machine in the movie 13 Ghosts. At the center of the device is a glass dome that appears to contain something resembling a cosmos. The rings spin, oscillate, and flip, and I with them. Looking toward the center, I say, “I am looking for the Self!”

Again, I hear a voice say, “Original sin.”

I don’t understand. Before I can ask for clarification, the ring I am standing on flips, propelling me through space. I am traveling faster than the speed of sound because I see sound barriers breaking around me. I see that I am fast approaching the Earth. Flames surround me as I enter the atmosphere, and I worry that I won’t slow down and will crash into the ground. I see the old-growth forest below me, and my body slams into the scorched wooden signpost, leaving a bloodied corpse impaled, while the speed of my travel sends my spirit through the ground and into an underground ocean. I look up at my corpse and determine that I need to continue searching for the Self.

I swim deeper and deeper into the ocean until I come to an underwater cliff. I swim over the edge, and two giant eyes appear in the depths. I swim back toward the surface, looking back over my shoulder, I see a massive sea serpent swimming after me. I begin swimming at a supersonic rate, but then remember the importance of facing unconscious material head-on, and turn back around. I swim toward the serpent and begin to fight with it. I land a punch between its eyes, and it changes, shrinking, shrinking, until a small sea creature forms and floats in my hands. It is a small seahorse, happy and playful. It leads me over the cliff and deep into the crevice. We swim deeper and deeper, and the seahorse grows to a size that allows me to climb on his back and ride him into the depths.

We arrive at an underwater enchanted forest, and I thank my seahorse for delivering me to the destination. I step into the forest, whose trees are a silvery coral, and continue toward the heart of the forest. The coral’s branches grab me, and rather than resist, I submit. I am passed from one branch to another until I arrive at the opening: the center of the forest.

“I am looking for the Self!” I proclaim.

The ground erupts, and Cthulhu appears.

“You will not find the Self here!” He says.

“I am not afraid of you. You have prevented me from reaching the Self before, but you will not again.”

I see him, and remember the Queen of the Damned’s wings, and how they reminded me of Cthulhu’s.

“The Queen of the Damned is your consort, isn’t she? She escaped her prison because of me. She destroyed my forest. I suspect you are hoping that I will set you free. What destruction will you unleash if you reach the surface?”

Cthulhu remains silent, staring at me.

“My mission is not to stop you, nor is it to help you. I seek the Self. Do what you will.”

Cthulhu laughs and surges upward, frantically breaking through what appears to be stone above us, and continues making his way to the surface.

Again, like at the end of my previous vision with the old-growth forest ablaze, I find myself wondering what destruction is about to be unleashed upon the world.

I sit on the ground and draw a heart in the sand. I close my eyes and think, “I seek the Self.”

The sand swallows me, and I am moved through a tunnel filled with eyes. It reminds me of Alex Grey’s Collective Vision.

As I move through the tunnel, I repeatedly say, “I am seeking the Self.”

The voices of many, in unison, reply, “No man can behold, and afterward remain in the flesh.”

“I have died,” I say, pointing to my impaled corpse way off in the distance.

“You have died once,” comes the voice of the many, “to understand death is required.”

Despite this, I continue pressing through the tunnel, hoping to arrive at the Self.

The tunnel of eyes begins to close off, and the voice of the many cries out, “You have not an eye single to the glory! Go back! Go back!”

I am then pulled out of the tunnel by an unseen force and land on the ground of the old-growth forest, reunited with my body, no longer dead, bloodied, and impaled.

Through this active imagination session, I came back up with insights, but also questions that I can’t seem to let go of. I went looking for the Self, and three different guardians told me, three different ways, that "looking" might be the wrong verb. Maybe that's the teaching. Maybe the Self isn't waiting, buried in a burned forest, in the vastness of space, or at the bottom of an ocean; I don't know yet (ask me in another year).

Where are you still digging for answers in a cavern when the part of you that already knows is standing right behind you, asking if you need a hand?

I’m lying in bed at 2 am (it’s a Tuesday, house is quiet, everyone else asleep) and I’m staring at the ceiling doing that thing where you review the whole inventory. All the boxes: checked. Life: achieved.

So why does it feel like I’m about to tell a waiter, this isn’t what I ordered?

It’s not like this is some dangling-from-a-cliff-in-a-movie scene. More like the chirp of a low-battery fire alarm I can’t seem to locate. And underneath the inventory, the thing I kept telling myself: you did everything right. You have nothing to complain about. People would kill for this life. Go to sleep.

You hate that you feel this. Because you did everything right. That’s the annoying part. The ceiling doesn’t care about your logic.

No good answer. Just the ceiling.

The Myth of the Midlife Crisis

We’ve turned this into a punchline. Guy turns forty-five, buys a sports car, maybe has an affair, gets a tribal tattoo, and buys a gym membership. We laugh about it. We dismiss it.

But underneath the clichés, the psyche has been building toward something for decades — and it’s not going to wait for you to be ready.

Jung called it individuation — one of those words that sounds impressive until you try to explain it at 11 pm. Skip the technical version. What it actually is: you spend the first half of your life building an identity out of Papier-mâché. Your parents’ expectations (and their parents’ expectations, handed down like furniture you didn’t ask for). Whatever your industry calls success. The life your neighbors seem to have, based on what they post. You build a house with it. Photographs well.

Around midlife, the psyche starts checking the load-bearing walls. It seems to ask How certain are you these will hold? Let’s find out! Then the pressure starts to be applied, and the cracks start forming. Most people deal with it by repainting the exterior.

The First Half of Life vs. The Second

Career, reputation, respect: the whole architecture. You built it piece by piece, and it’s standing. That was the point.

Here’s what I wish someone had told me leading up to thirty-seven, instead of letting me figure it out via ceiling insomnia: there’s a second game. Jung called the first one “building the ego”: creating an identity, establishing yourself, proving you can survive and succeed. You do need this part of life.

The second half is something different: taking apart what you built and figuring out which pieces are actually yours. It’s about meeting the parts of yourself you sacrificed to become successful. The creative kid you shut down because art doesn’t pay the bills (and now you paint walls in your house a very safe shade of gray). Remember having opinions? Before the conference room trained that out of you? Maybe even the person who wanted to write, or travel, or do something that didn’t have an ROI attached to it, the one you stopped mentioning at dinner parties because the conversation moved on too quickly.

The crisis happens right at that transition. You’ve mastered the first game, and now the rules are changing — and nobody gives you the new playbook. Because there isn’t one. I looked. I even asked my Jungian Analyst, who essentially said, “Yeah, that’s the point.”

What Your Unconscious Is Trying to Tell You

When I hit my own version of this (mid-thirties, corporate job that looked great on LinkedIn, four kids, a mortgage, the whole architecture of a life I was supposed to want), my dreams started to suggest otherwise.

I started having dreams so vivid I’d wake up genuinely disoriented, unsure for a moment which world was real. A Dream about a massive wall near my corporate office collapsing because the machine boring into it misaligned (Freud would easily spot the word play here; do you?).

I ignored them for months. Told myself it was stress. Bad sleep. Too much caffeine. The usual suspects.

What finally moved something wasn’t more midnight reading. It was a fellow dream worker. I’d been attempting to solve this solo, and then, within one session with my colleague, it clicked. I described the collapsing wall dream, and she said something I wasn’t expecting: “If this were my dream, that doesn’t feel like a warning. That feels like a needed demolition. My conscious part wanted to drill a clean hole through the wall, but I haven’t been aligned with my unconscious, so the entire wall is being deliberately taken down.”

The unconscious gives zero shits about your pre-determined plans if there is misalignment (in my experience, at least, and from what I’ve watched with clients). The irritability that doesn’t match your circumstances. The feeling that you’re going through motions that used to mean something and don’t anymore. It can often feel like what’s the point?

That can also be depression, genuinely, and if it is, please talk to someone who isn’t me. But I’ve seen enough people in that in-between state to notice something: underneath a lot of what gets labeled midlife depression is something older. A self that’s been waiting for decades, getting increasingly dissatisfied about being neglected: it has its own agenda, and wholeness is on the agenda. When you’ve shelved significant parts of yourself for decades, those parts start making noise. First in dreams. Then in restlessness. Then, in the 2 am inventory, that won’t balance.

You can keep trying to ignore it, sleep through the chirps, or you can change the battery.

Why This Isn’t About Happiness

This isn’t a happiness project. It’s not about finding your bliss or building your vision board or whatever the Instagram therapists are selling this week.

It’s about wholeness. And wholeness includes the parts of yourself that are contradictory and, frankly, a little embarrassing to admit. It includes the shadow: all the qualities you’ve decided aren’t acceptable—the ambition you relabeled as greed somewhere around your late twenties. The anger, which, let’s be honest, was probably the first thing to go. And whatever that feeling is at 10 pm on a Sunday when the week ahead looks exactly like the one behind it.

The entire first half of life is partly designed to suppress exactly this kind of inquiry. The educational system, the career ladder, the mortgage; they all run more smoothly when you don’t stop to ask whether any of it is actually yours. The system requires assembled, functional people. Individuation is, at least partly, a subversive act.

Midlife isn’t asking you to be happier. It’s asking you to stop repainting and start renovating. Those are very different projects. One involves admitting the life you built might need renovating, perhaps a significant renovation. Some walls come down, papier-mâché replaced with wood and drywall. Some rooms get added. Maybe even foundation supports. The disassembly phase can genuinely feel awful; I can tell you from the inside, not just from observing it in clients.

And, as a heads up, from what I have read, and am starting to observe, what’s on the other side isn’t a finished product. It’s more like: a life that feels closer to yours.

Not someone else’s meal. Your meal. Just the way you ordered it. Which still has quirks (you’re really going to eat that?), but you know that it is yours, you know that you’re not simply ordering it because it is the best-selling item on the menu.

What I can’t tell you is how long it takes. That part, the unconscious has been working on without asking your permission. It doesn’t check your calendar.

The Dream Tells You First

My own dreams started months before the conscious crisis hit; the unconscious was already working on it, sending images and trying to get a word in while I was busy convincing myself that the ceiling was fascinating.

You write the first one off. Maybe the second. But the fourth one about those recurring images? The one that wakes you up and sits with you through breakfast? That one’s harder to dismiss.

The first thing I like to know when someone comes to me in the grip of this: what have you been dreaming? Why? The unconscious has likely been drawing up plans for renovation, making room, and packing boxes in the basement or the attic, while you continue going about in the living room, kitchen, and bedroom, insisting everything is fine. It might have started months ago, or maybe years.

What Now?

If the 2 am question is visiting you (before you buy the car, get the tattoo, ok maybe go ahead with that tattoo, I’ll even recommend the artists, or decide it’s all just burnout), write down at least one dream. Not to analyze it. Just to acknowledge it happened. I use a pencil and paper or (an app, not affiliated; I’ve just been using it for two years, and the developers seem to understand that recording a dream at 5:45 am means you need a fast, dark screen with minimal friction). You might be surprised at what’s been trying to get your attention.

The clients I’ve seen handle this best (and I’m including myself in that category, qualified as it is) stopped trying to solve it. They started asking what the dream is actually trying to say.

The dreams you wrote off as stress or anxiety — what might they actually be trying to tell you?

I know how that might sound. A grown-ass man with certifications in Jungian coaching and dreamwork, tucking a note under his pillow like a kid leaves a tooth for the tooth fairy. But dream incubation — asking your unconscious a specific question before sleep — is one of the oldest healing practices humans have ever devised (assuming humans devised it in the first place). And I keep doing it because it works, even when the answers aren't what I expect.

That night, I dreamed I was standing in a forest at dawn. Beams of sunlight cut through the canopy. In front of me: a massive tree — possibly a sequoia — already cut down. A two-man saw was propped against the stump.

That was it. No drama, no chase scene, no dead relatives delivering cryptic monologues. Just a forest, a stump, and a saw that takes two people to operate.

The sequoia — majestic, reddish-brown, something I've never seen in person but have always found striking — had been felled. By whom? The saw was a two-man tool. I remembered using one in Boy Scouts; the teeth were dull, and it took real effort. Nothing about it was quick or clean.

If the tree represented my anger — this massive, rooted, alive thing — then someone had already helped me cut it down. Or maybe the tree wasn't the anger at all. Maybe it was the vitality I'd been severing. Maybe my anger outbursts weren't the disease; they were the symptom of something essential being removed. And the two-man saw meant I wasn't doing it alone; perhaps, an unconscious part of my psyche was helping me sabotage myself.

I'd asked how to resolve my anger. Instead of handing me a fix, the dream acted like a coach, looking at the dilemma from a different angle. It was as if the dream were asking me to consider: What if the anger isn't the problem?

The Greeks Had a Building for This

Three thousand years before I shoved a note under my pillow, the Greeks built entire temple complexes — Asklepieia — dedicated to the same idea. You showed up sick, injured, or lost. You bathed. You fasted. You made an offering to Asclepius, the god of healing. Then you slept in a sacred chamber called the abaton, holding your question or prayer in mind, and waited for the god to visit you in a dream.

Temple priests interpreted what came through. Sometimes the dream prescribed a treatment. Sometimes the dream was the treatment; it restored whatever spiritual imbalance had manifested as a physical affliction. According to inscriptions at Epidaurus, these dreams were said to relieve more than symptoms—they could change your fate.

I think about this whenever someone tells me dreams are "just your brain processing the day." The Greeks built temples for this. The Egyptians wrote instruction manuals. Cultures across the world developed specific rituals for calling in healing dreams. To me, this suggests these are not merely folk superstitions, or obscure esoterica, but systematic practices with preparation, intention, and interpretation built in.

We forgot all of that. Somewhere between Plato and Netflix, we decided the night was for recovery at best and wasted time at worst. We stretch our waking hours until they snap, choosing one more episode over the thing that might actually help: our dreams. Heraclitus had it right twenty-five hundred years ago: "The waking have one world in common; sleepers turn aside each into a world of their own." We've been avoiding that private world as if it were a load of laundry to be folded or a sink full of dirty dishes.

How to Ask

Dream incubation isn't complicated. What it requires is the same thing the Greeks signaled with their fasting and offerings: intention.

Here's the version that doesn't require a temple.

Start by getting honest about what you're actually asking. Not the surface question, the real one. "Should I take this job?" might really be "What am I afraid will happen if I stay?" My anger question felt straightforward, but the dream suggested I might be asking the wrong question entirely.

Write it down. Something shifts when the question moves from spinning in your head to sitting on paper. It doesn't have to be fancy; a torn piece of paper will do. Write it the way you'd ask a friend.

Before sleep, reflect on the question. You don't have to obsess over it; just let it be part of your awareness as you drift to sleep. Some people visualize it; I just read the card a few times and put it under my pillow. The Greeks bathed and made offerings; your version might be an Epsom salt bath, turning off screens an hour early, or reading something that matters to you instead of doomscrolling. The point isn't the ritual, it's how you choose to signal to your unconscious that you're paying attention.

Then catch whatever comes. It might not arrive on the first night. When I incubated a question during my training at the Institute for Dream Studies — show me a guiding image for my time here — I had a dream about playing golf in Spain at midnight with a broken watch. Not exactly a clear directive. But the confusion in that dream, the sense of being in a beautiful place while anxiously calculating whether I'd make it back in time, told me something important about how I was approaching the program: one foot in, one foot already trying to figure out the next thing.

Even fragments count. A feeling counts. Write it down before you reach for your phone. If you remember nothing, write that: I didn't recall a dream, but I know I dreamed, and I'm listening. The act of showing up for the dream — consistently, patiently — is what opens the channel.

The Night Is Not Wasted Time

Freud thought dreams restored psychic balance by fulfilling wishes we couldn't admit to while awake. Jung saw them as compensatory, the unconscious correcting for whatever our waking attitude had gotten wrong. Both agreed on one thing: the dream is working on something, whether you participate or not.

The difference between letting your dreams run unattended and practicing incubation is the difference between overhearing a conversation and joining it. You're not attempting to control what the unconscious says. You're telling it you're listening, and willing to act.

The Greeks slept in temples. You have a pillow and a pen. The practice is the same: ask a real question, prepare yourself to receive, and trust that the night has something to offer besides rest.

What question have you been carrying that your waking mind can't seem to answer? Write it down tonight. Put it somewhere you'll see it before you close your eyes. And pay attention to what comes. Not just the first night, but over the week that follows.

Your dreams are already working on something. You might as well find out what.

I woke up and, as I was writing down my dream, I had a bit of a laugh thinking that, if I had Googled ‘teeth rotting,’ it would have told me it means anxiety. Thanks, Google.

Here’s the thing about dream dictionaries: they’re not wrong, exactly. They’re just lazy. “Teeth falling out = anxiety” is like saying “crying = sad.” Sure, sometimes. But if you stop there, you miss everything.

That dream wasn’t merely about anxiety. It was also about the gap between what we polish for other people and what we let decay where no one’s looking. The man who looked in the mirror wasn’t worried about his teeth; he was proud of his decision to get veneers and couldn’t care less about the rot below, so long as others didn’t see it.

Rather than turn to Google, AI, or Reddit, I became curious.

Where in my life was I doing that? Veneers on top, decay underneath?

Where was I investing in the visible version of myself while ignoring the parts “no one really sees”?

Individuals familiar with Jung’s work might point to that and suggest that it represents the Persona, a mask we wear for the world. I don’t love that word here because it makes it sound intellectual when the dream made it visceral. The image of rotting teeth behind a perfect smile does more work than any conceptual term could.

The Problem with Symbol Dictionaries

Nearly all dream websites seem to operate like a math equation: Water = emotions. House = self. Car = control. Snake = fear (or sex, depending on which site you trust). Add it all together? The dream means you have a strong emotional reaction to trying to have self-control around sex. Makes sense—if you are a pop-psych Freudian.

It’s not that these are wrong. It’s that they flatten something alive into something dead. Your dream chose that specific image for a reason. Not “teeth” in general — those teeth, in that mirror, with that man’s satisfaction and disregard for rot. The meaning lives in the details the dictionary throws away.

Water in your dream isn’t “emotions.” It’s that water — the still lake, the flooded kitchen, the ocean you won’t enter. The specificity is the message. When you reduce it to a symbol-equals-meaning equation, you’re doing to the dream what the man did to his teeth: polishing the surface and ignoring what’s underneath.

The Stranger in the Diner

Back in 2014, I had what I consider a big dream—one of those long, layered ones that stays with you for years.

I’m sitting on a barstool in a diner. A waitress tells me they’re closing and that I need to leave. But I can’t. I’m waiting for someone, a woman I can’t name, can’t describe, but I know she’s supposed to be here.

“She? Are you waiting for someone?” the waitress asks.

“Yes. I mean, no. I…” The words are hard to find.

I look around and discover that the diner is suddenly empty. I’m sitting in the dark with passing headlights casting shadows on the walls, and I still won’t move. Some paralyzing certainty that if I leave, I’ll miss her.

Then the diner shifts. Same place, yet it seems different; the colors are more vibrant, almost as if each object and person were generating color from their very being. An old man sits beside me, sips his coffee, picks up his newspaper, and says: “She’s not here, son.”

We go back and forth. I don’t know who “she” is. He knows I don’t know. He finds this amusing.

He takes his sweet time — another sip, folding his newspaper, collecting his things — is he leaving already? There has to be more than our brief exchange! He says, “My boy, you will learn that April showers indeed bring May flowers, but if you spend all your time anticipating the rain, you’ll forget about the reason you wanted it to come in the first place.”

He shakes my hand and tells me, “She will come. Joy and happiness will come with her. But don’t spend your entire life waiting. Live, love, and experience life as if there were no April showers, and find your own way to those May flowers.”

Now. If I’d typed “stranger in dream meaning” into Google, I’d likely get: “The stranger represents your shadow, the parts of yourself you’ve rejected.”

Does that cover it? Does “shadow” capture an old man in a diner who knows more about my life than I do, who speaks in Better Home & Garden type metaphors and laughs at my confusion? Does it capture the woman I’m waiting for, who hasn’t arrived, and what keeps me sitting in that diner?

For me, that dream was about how I was putting my life on hold for something I couldn’t even name. The old man wasn’t my “shadow.” He was the part of me that already knew I was wasting time, and found it funny that I hadn’t figured it out yet.

Dream dictionaries give you a word. The dream gives you a world. And if you stop at the word, you never walk through the door.

What to Do Instead of Googling

Write it down. Everything. The stained teeth. The empty diner. The old man’s coffee cup. Before you interpret, before you analyze, capture the damn thing.

Then sit with it. Not the meaning. The feeling. What did it feel like to see those rotting teeth? What did it feel like to sit in that diner, refusing to leave?

The meaning shows up when you stop chasing it. Perhaps, days later, in the shower, when you’re thinking about something else entirely.

If you want a structure for this, I put together a free dream journal guide—questions you can ask every dream, and how to start remembering more of them. Grab it here.

What image from a dream has stayed with you despite asking Google or AI about it? And what would happen if you stopped Googling it and started listening to it instead?