The cycles of transformation

Birthing what wants to emerge

Nov 30, 2025

“Hey Claude, how many weeks has it been since March 3rd, 2025?”

37 weeks.

Seeing that number flash back, and even now, I feel something settle in my system. It’s as if some energy that had been dancing around in my head dropped into my body. If I had to put words to it: “Oh, of course, that’s what’s been happening. That’s where we’re at: 37 weeks into the job search journey.”

The common metaphor for transformation is the cocoon. The caterpillar liquifies, emerging with wings. I appreciate it, but it doesn’t feel quite right. The larva is alone, unconscious, passive. But then I thought of being in a womb, and when I saw ‘37 weeks,’ it clicked: the human birth process. Transformation isn’t happening to you; it’s a process you’re consciously stewarding.

Tracing back the last few years of my life, I found they break down into these 8-10 month cycles, the duration of pregnancy. Each has entailed an unfolding of layers of identity, birthing a deeper experiencing of ‘who I am.’

Transformation is almost always a confusing process. You’re quite literally stepping away from the familiar, comforting contours of a way of being, one that also no longer serves you. But when you’ve spent months floating in uncertainty with no sense of where you are or what’s happening, the hardship can feel meaningless. You question everything: “Am I making progress or just stuck?” The hardship has no container, no shape. It’s just endless. And hearing a platitude like “The only way is through” doesn’t help—it’s just empty words without emotional resonance.

Archetypal stories give our hardships a container to rest in. They remind us we’re not alone, that others have walked this path. So often, we turn to the hero’s journey or the cocoon, dramatic transformations with clear triumph. But the birthing process resonates more with me. It’s gentler, more natural. Maternal. Less about slaying dragons and growing wings, and more about the quiet, steady work of becoming ready.

As a man, I find this metaphor beautiful. I’m not claiming to know what actual pregnancy feels like, nor will I ever. I’m just mapping my experience with some assistance from Claude, with the hope that it may resonate with one of you and be of support when life as you know it begins to fall apart.

First Trimester (Weeks 1-13)

The process is barely noticeable. You’re aware something is underway, but it’s not visible or fully ‘real’ to you or observers. In a transformative process, it’s often the commitment or intention, like leaving a job or cultivating secure attachment. There’s the excitement of “What’s life gonna be like?” and fear of “Am I ready to lose this?” You’ve just begun to sense into the possibility of what life could be like.

My move to San Francisco in February marked the end of one cycle and the beginning of another. Pretty immediately, I began grappling with the sense that something was ‘off’ despite my long-held vision materializing. On March 3rd, I felt the ‘yes’ to commit to returning to a job. It’s what wanted to happen.

I felt both relief and an antsiness I hadn’t realized was there. I wanted ‘it’ to happen quickly, like it did when I left investment banking. In hindsight, it’s clear I intellectually felt ready, but didn’t feel ready in an embodied way. I don’t know if a first-time mother is either at this point.

In mid-April, an opportunity with The Commons appeared that felt aligned. I began to feel into what an integrated life could look like. One where my day job is imbued with the essence of what I care about most: collective healing and transformation. One where my life isn’t siloed into pockets of ‘more’ or ‘less’ alive and aligned, but instead, seamless. Whole.

Looking back, I think the work of this trimester is to allow the commitment or intention to settle. To not try and rush into any big decisions, but instead to feel into the possibility of what could emerge. We often want it to happen now, because life will obviously be ‘better’ if we were already ‘there’ in an aligned job or feeling more securely attached. Not realizing that the journey itself is what allows this life to emerge.

Second Trimester (Weeks 14-27)

“Okay, this is really happening.”

There’s more settling and acceptance of what’s happening, bringing energy and movement. By this point, I’d been in conversations with The Commons for months. Truthfully, a Part of me felt like it was destined to happen. It felt too perfect. In hindsight, I recognize this same Part tried to make it a fit. Tried to rush towards an integrated life sooner rather than later, and avoid the discomfort and difficulty that would follow in the coming months.

I’ve realized the first trimester is often the honeymoon period. Once it wears off, the reality of the process is revealed. One where the questioning and emotions don’t disappear, but instead, intensify. You’re in a spin cycle, knocked off center over and over again, praying for it to ease up.

At the end of June, I found out that The Commons went with someone else, and it rocked me. Questions swirled like: “If not this, then what?” and “Am I ever going to find something that brings me alive?” I felt seriously lost, unsure of how or where to proceed. I needed the RV trip in Washington to reset, be in nature, and find some ground. I had to touch grass and sit in a river.

Returning, I continued to live the question “What does an integrated life look like?” I began exploring consciousness venture capital as a possible path, which brought some aliveness. I co-hosted a two-week pop-up village in Antigua, which brought even more aliveness.

As difficult as transformation is, it’s important to ground and relax into what’s happening. A lot is churning and turning within you; life is literally being born. And while it’s instinctual to reach for control, it’s a process entirely out of your hands. To the best of your ability, all you can do is allow the river to flow and carry you for a ride. All the while, recognizing how far you’ve already come from where you’ve started, and what already feels different in your being, even if it’s subtle.

Third Trimester (Weeks 28-40+)

“I’m tired.”

At this point, there’s a physical and existential heaviness and exhaustion that comes from carrying something for so long. And of course, emotional distress. Perhaps impatience or readiness for this all to be over with and to get on with life’s regular programming. It’s quite literally backbreaking work to be in this process for so long.

For months, I couldn’t admit I was tired. I have Parts of me who don’t think tired is an option, shaped by immigrant parents who never stopped working and never complained. These Parts keep me trudging on and presenting an appearance that everything is going swimmingly. Easy peasy! Even when that couldn’t be further from the truth. All I wanted to do was curl up, cry, and wait for the process to all be over.

When I didn’t get the Imbue job, I felt even more ungrounded than I had with The Commons. Imbue felt so aligned and alive in an embodied way that it broke some Part of me that believed “When you want something, all the Universe conspires in helping you to achieve it.” This same Part that pushed me to start following my dreams and aliveness.

Once more, I needed to rest and reset. I went on a week-long meditation retreat in Ojai. I spent the days sleeping in a tent, eating nourishing food, meditating, and connecting. I came back rejuvenated and inspired for the next stretch of the process. This trip reaffirmed to me in a deep way that it’s okay, and needed, to rest, wherever I am. I don’t have to earn it.

After Imbue, I’ve been resting in “I have no idea what the hell is happening…Do I ever?” This process has shown me “No, you don’t, and that’s okay.” It’s often our own conditioned expectations of how we should be that make the process far more draining. We exert energy performing rather than simply allowing ourselves to be as we are.

The process, be it birth or transformation, is the journey of embodying the readiness to navigate whatever greets you on ‘the other side.’ Reading books on how to be a mother doesn’t prepare you to be a mother. Readiness comes from 8-10 months of constant attunement. Learning to witness your needs, hold space for your emotions, nourish yourself through the uncertainty, and ask for support when needed. You’re building the capacity to be present with what’s emerging. In this way, transformation is a witnessing, holding, and experiencing. More a birthing than a cocooning.

When people ask me how I’m feeling about the job search, I tell them there’s this felt sense of ‘readiness.’ Yes, there are still emotions, but they emerge within a deep ground and steadiness that has matured through this process. The huge emotional swings I felt even a month ago have quieted. By being present with myself throughout this entire experience, attuning to and holding space for everything, I feel truly ready for what wants to emerge. And with that, there’s a sense of ‘it’s coming.’ Like a mother feels her baby’s impending arrival, the job feels on the horizon. More of a ‘when’ rather than an ‘if.’

Each trimester developed something in me. The first taught me to sit with uncertainty without rushing. The second taught me to stay grounded when life doesn’t go as planned, and to let go of the planning. The third taught me to hold the full spectrum—despair and joy, helplessness and gratitude—without judgment. This is what I mean by readiness. Not knowing what’s coming, but trusting you can meet it.

Towards the end of a transformative process, a way of being that once felt foreign or unreal is happening. It’s yours to birth. And the longer you’ve been in it, the more ready you feel for its eventual emergence. You’re just patiently waiting now. There’s a deep okayness. Not excitement, not frustration, just readiness. A stillness.

That’s not to say I don’t feel tired. Every day, even if I haven’t consciously thought about the job search, it’s been present. It’s been challenging for me to go through this, to have no idea what the fuck is going on. To have felt total despair, helplessness, and aloneness. To have felt joy, gratitude, and a sense of breaking through. Through it all, I’ve realized I am the container, womb, holding everything.

And maybe that’s the thing: the birthing process and cycles of transformation aren’t just for creating a new life or way of being. They’re about preparing us, again and again, to meet what wants to arrive. And it isn’t just the new job, the healed attachment, the integrated life.

It’s you.