Photo by City of Gold Coast

Welcoming the Healthy Masculine Home

Embodying sacred union within myself and Grail Leadership

Holly McCann
Published in
18 min readJan 14, 2023

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“The Self then functions as a union of opposites and thus constitutes the most immediate experience of the Divine which it is psychologically possible to imagine.” ~ C.G. Jung

I am profoundly grateful for the wealth of multi-faceted gifts I continue to receive from Grail Leadership ~ the body of work that is emerging through me as its visionary and one of its founding co-creators.

As with all great muses, it continues to inspire me, challenge me, and educate me about its true nature. One of its primary lessons is that Grail leaders do not lead from command nor control, but rather as living examples of what is possible. Our visions for a thriving future become reality only as we embody them ~ as we ‘be the change we wish to see’ and radiate that out into the world.

The path of the Grail leader is not for the faint of heart. It increasingly demands nothing less than utter devotion to realizing our vision and fulfilling our mission, bringing every bit of our being into full alignment and integrity with that endeavor.

A core principle of Grail Leadership is what I refer to as Sovereign Unity ~ the state in which seemingly opposing polarities are dancing in harmony. In other words, operating in alignment with the life-giving, regenerative principles of Nature.

If you are reading this, you are one of the pioneers of our emerging future in which humans and the Earth exist in a state of abundance and mutual thriving. This is our natural state of being ~ one that is increasingly accessible to us the more we’re operating in Sovereign Unity.

This is the third in a three-part series of articles. You can read the first two here: (1) Restoring the Feminine to Birth a Whole New Vision and (2) Forgiving My Wounded Masculine.

Heroic journeys

Photo by Bailey Zindel

Our lives are the hero’s/heroine’s journey of legends ~ the voyage from separation into sacred union of the masculine and feminine polarities within. As we follow the breadcrumb trail of our experiences through many initiations and threshold crossings, we are alchemizing the wounds and distortions we took on while walled off from parts of ourselves. Ultimately, we’re able to integrate these vital aspects into wholeness.

This is the epic quest for the Wholly Grail.

This heroic journey is an archetypal one, with several phases that we all progress through in our own individual ways and timing.

Throughout 2021, I was trekking through Central and South America ~ and through the phase of my heroic journey known as the Healing of the Wounded Masculine.

In mid-2022, I set out on another excursion ~ one that spanned six months through Portugal, Italy, Scotland and Australia … and into the culminating phase of integrating my {healed} masculine with my feminine.

While visions of a book about Grail Leadership had been dancing in my head for quite some time, they kicked into full-speed Highland dancing as soon as I set foot in Scotland. I was being flooded with inspiration and intuitive insights about a mythic, multi-dimensional origin story that would both inform and activate the reader in the nature-based principles of Grail Leadership.

I was led down numerous rabbit holes of research that would both confirm some of my insights and simultaneously open pathways to several more. At times, I felt like I’d been plugged into a universal library with access to the secrets of the ancient history of humans and the Earth, overwhelmed with a feeling that I might spontaneously combust as all this information and energy coursed through my system.

So, as I set out for the Sunshine Coast of Australia where I would spend six weeks with my co-creator in Grail Leadership, I thought I had the trip all figured out: Julia would help me bring all the ideas and information scattered in my brain into a book outline with a coherent story arc; and I would help her set up some offerings about Grail Leadership that she was chomping at the bit to implement.

Ahh, the best-laid plans of mice and men….

The need for a pathway

Photo by Khachik Simonian

After beginning the day with a sunrise beach walk, Julia and I sat down to discuss the “work” we wanted to do during our time together. As we always do at the beginning of our sessions together, we went within ~ tuning into ourselves and each other so we can be fully present and focused.

After several minutes of silence and deep listening, Julia said something I don’t usually hear these days ~ that my presence felt extremely chaotic, and that there was so much energy swirling around {especially in my mental space} that it was difficult to connect with me. Oomph!

And then she said something that would set the tone for my entire stay: “All that energy is swirling around so forcefully because it has nowhere to go. It needs a pathway.”

Tears started streaming as my body felt the prophetic truth in her words.

And, for a few minutes, I still thought that pathway would be a book…. {cue snickering from the cosmic peanut gallery}

Julia began sharing what she was experiencing in the two round tables she was facilitating at the time. People were hungry for what Grail Leadership has to offer, starving in fact. They were lighting up like crazy as she shared even small aspects of what had been emerging through us over the past few years, inspired and enlivened by tremendous possibility in areas where they had begun to feel stuck, hopeless and defeated.

With a great deal of fire and passion, Julia said, “We have to find ways to finally get this model out there. It’s time. People are really ready for it!”

I could feel a nervous excitement stirring within me. After years of crystallizing the vision of Grail Leadership, moving through incredible layers of personal transformation and embodiment of its principles, attempting to get it out there and pulling back in a cha-cha dance of premature starts….

I began to let it sink in that it was well and truly time for this vision to land.

The leaders are ready. Grail Leadership is ready.

But … were we ready?

Ready … or not?

Photo by Joshua Sortino

In navigating through my hero’s/heroine’s journey, I’ve come to recognize one of the most brilliant features of this archetypal design. Every time we’re about to cross a threshold into a new phase, after having passed through the requisite initiations of the current one, we encounter what I call “tripwires.”

As you come close to the threshold crossing, some part of you knowing it’s time to move on, you’re stopped in your tracks. As if you’ve just tried to walk out of the Smithsonian with the Hope Diamond in your pocket, you’re surrounded by deafening alarm bells, blinding strobe lights and booming voices of “the authorities.”

Freeze! Hold it right there! Are you sure you have permission to go there? Prove it!

Before you know it, you’re hopping across yet another set of coals. But this time, as you reach the other side of the fire-walk, a big grin spreads across your face as you realize this was just a tripwire.

You see, tripwires are little tests set up {by ourselves, at some level} to prove {to ourselves} that we are truly ready to move forward ~ that we are capable of accessing this increased power with great responsibility and integrity. What an ingenious fail-safe mechanism!

How can you tell the difference between a tripwire and a full-blown initiation? You usually sail through a tripwire quickly and nimbly, like a ninja on monkey bars. It doesn’t take you down, leaving you raw and in need of a lot of space and time to integrate and recover. And you exit it with a deep appreciation for how far you’ve come and how well you’ve embodied the wisdom of that phase. At that point, you know you have everything it takes to cross into the next phase of your journey!

Julia and I didn’t see them coming {do we ever?}, but we were about to cross through three tripwires ~ with warp speed and ninja agility….

Preserving the integrity of a big vision

Photo by Grooveland Designs

As Julia shared her ideas for getting Grail Leadership out into the world ~ through articles, short presentations, workshops, and podcasts ~ I sensed a lot of resistance rising in me.

As we’ve done so many times before, we began to sort through this wobble in true Grail fashion ~ speaking it into “the chalice”, stirring it around a bit, and seeing what surfaces.

I shared my frustration at what seemed like a double bind. I felt compelled to find a way to present Grail Leadership in its entirety, protecting it from the distortions I know can happen when the pieces are separated from the whole. At the same time, I knew we needed to be able to communicate it in a way that would be approachable and digestible.

This body of work is so multi-faceted, multi-layered and relational ~ each principle intimately intertwined with the others. I was worried that, by chopping it up into parts, it would lose its synergetic essence.

“The ability to consider wholeness is, at some point, an intuitive sense rather than a logical one, for it’s the combined behavior of integrated parts that is being discerned, rather than just the behavior of the parts themselves.” ~ Marshall Lefferts, “Cosmometry”

Strong emotions were coming up, along with gruesome analogies of dismemberment. I realized this was stemming from some deep transpersonal trauma of the separation age, as I found myself repeatedly saying some variation of this belief: “If it’s fragmented, it will get distorted. That’s exactly what has led to eons of pain and suffering in the world!”

This is one of the reasons I’d been warming up to the idea of writing a book. If I could present Grail Leadership in a complete picture, then people could go at their own pace and receive from it whatever resonated, but at least there would be an original source that was whole and intact. While bits of it could be twisted, that source could be used to clarify anything that had been misunderstood or taken out of context.

Julia reflected that through our conversation she was getting a deeper understanding of what it means to be a visionary, the challenges of holding a big vision for something that has never been before, and the devotion to bringing it into form intact and free of perversion.

She also shared her wisdom that, while it’s important for the visionary to hold a cohesive vision in its entirety, very few people would ever be able to grasp all of it ~ certainly not all at once. And they don’t need to. They just need to access the bits that at the time are a match for them and their mission, which is connected to that greater whole.

I felt a tremendous sense of relief {and a bit of a forehead-slap moment} ~ of course, that is exactly what co-creation around a shared vision is all about!

I just needed to see my “distortion from fragmentation” fear {which had reached its expiration date} and the rule that I’d unknowingly created from it: that the only way to preserve the integrity of Grail Leadership was to maintain it as one comprehensive unit.

Dancing through this trip-wire showed me how deeply the values of wholeness and integrity reside within me. And, in moving through it, I was able to release the vice-like grip I didn’t know I’d been holding around Grail Leadership in the name of protecting it.

Retrieving the baby from the bathwater

Photo by Jernej Graj

With the concerns about partiality resolved, it felt like Grail Leadership had been unleashed. Julia and I found ourselves over the next few days engaged in exciting conversations, lit up by so many inspired ideas. We mapped out offerings we could create to not only share the core concepts of Grail Leadership, in ways where they could be easily and meaningfully implemented, but also to provide round-table experiences to directly engage with and embody true co-creation.

Within the span of a week, we had laid out a beautiful framework for expressing Grail Leadership in stepwise stages for individuals and groups ~ complete with self-selecting pathways {yes, pathways!} where pioneering leaders could choose to go deeper based on their own resonance and timing.

At some point, I stopped and half-jokingly said, “Hold on… did we just create a whole marketing and sales funnel? I swore I would never do this again!” Julia laughed and said, “I know, me too! Who are we?!”

After years of implementing those information-marketing systems to great success in my coaching business, I had rejected them entirely as I moved through the Dark Night of the Soul phase. Through my deep-dive into the underworld realm of the feminine, I had thrown out all these forms as being part of the ‘toxic masculine’ way of doing business.

Yet here I was, having so much fun exercising skills I hadn’t used in years. I really had to check in ~ is this okay? have I really gone off the rails here? am I out of integrity with my values?

As Julia and I talked through our surprise at finding so much joy in these activities of our former lives, and checked our motives for any lingering imbalances, we quickly realized what Grail Leadership has shown us time and time again….

It is not what we’re doing, it’s the energy we’re bringing to it. Of course! {slaps forehead again}

Marketing and sales were never wrong or bad. The flaws we had seen and felt in those systems were due to the energies of scarcity, inauthenticity and varying degrees of manipulation and pressure that were often being run through them.

It felt so satisfying to realize how far we’d come in cleansing our systems of those energies, knowing that the framework we were mapping out was arising out of our true nature and our desire to share our respective genius.

We were not creating “marketing and sales funnels” out of any need for people to buy or engage so that we could feel safe or valued. We were now engaging our healthy masculine to create pathways for engagement, building supportive structures that would deliver optimal value for the leaders we are uniquely designed to serve.

We were focused on all that we’re excited to give, from a centered place of fullness, rather than what we need to get to fill some perceived lack.

We had retrieved the masculine baby we’d thrown out with the bathwater!

There was one more tripwire waiting just up ahead…

Protecting my genius from prostitution

“Truth Coming Out of Her Well” by Jean-Léon Gérôme

Over the next week or so, Julia and I continued to refine the pathways for sharing Grail Leadership. We were constantly in awe and appreciation as more pieces of the puzzle revealed themselves, bringing the whole framework into even greater coherence and amplifying the toroidal, regenerative flow that is so characteristic of this model.

As we started putting price tags on some of the larger offerings, I felt a mounting uneasiness. What is this? Hadn’t I resolved my hangups around receiving money years ago?

Back to the chalice!

Over a delicious meal, sitting on floor cushions at Julia’s fabulous round table, I was sharing the voices of worry that were coming up for me: “This is all happening at a time when we’re both feeling a pinch around income. How do we know we don’t have a blind spot and are actually being motivated by some lack-based need for money?”

And then I felt the strong emotions as I began sharing about my time in Florence earlier in the year. While I was in awe, immersed in a mind-boggling array of incredible Renaissance-era art, I could also see and sense its shadow side: “So many of these artists felt trapped by their agreements to serve their patrons, taking on commissions that they weren’t aligned with as a way to meet their basic needs for survival. In many cases, it killed their genius. Grail Leadership is so sacred to me, so closely connected to my genius, and I don’t want to dishonor it by putting that kind of pressure on it!”

I could almost feel the feminine in me, shoulders on hips, declaring that she will never allow herself to be “whored out” again. Oof!

Clearly some strong energies that needed to be resolved if we were to move forward, expressing our genius in the world and receiving income along with it….

And it’s quite a familiar one, isn’t it? I see so many of us who have extraordinary gifts to offer, with great potential to benefit people and the planet, who keep getting derailed when money is brought into the picture. Like peeling an onion, we break through layers of it, only to have it come up again in new and different ways.

There is much to say about money and the remarkable assistance it provides in our heroic journeys, but that’s a topic for another article. Relevant to this one, money was showing up as a tripwire, daring me to engage with it to see just how far I’d progressed in transmuting my lack-based beliefs.

Once those voices in my head had their say, Julia replied with a voice that came from the beyond: “I hear you. I can see how it may look that way, and it’s good to check ourselves. But, I’d say at this point we are pretty damned incorruptible!”

Tears of truth flowed as a lifelong thread that connected money to my survival ~ a thread that was now quite frayed and tattered ~ finally let go.

Yet again, the tripwire experience was reflecting back to me how firmly I had embodied Grail Leadership ~ one of its foundational principles being that at the heart of any healthy, regenerative organization or initiative is a small group of “incorruptibles.”

Who are the incorruptibles? They are the Grail leaders ~ those who have navigated their heroic journey into wholeness and integration, who will not be swayed in their actions by external needs for money, power or control. They are motivated by devotion to their mission, having so embodied its core values that they radiate it from every pore in their being and lead by example. These are the true stewards of our mutually thriving future.

For years I’d been contemplating this idea, talking about it and writing about it. In that moment, I felt the deep cellular knowing in my body that what Julia said was true: we had embodied the wisdom and ethos of Grail Leadership to such an extent that we had become incorruptible.

Unaware at the time, this is what I needed to prove to myself before moving forward. Before I could share the powerful wisdom of Grail Leadership, I needed to know it was not just a set of mental concepts, theories or hollow ideals. I needed to know that we would not be causing more harm through distorted, immature expressions of it. I needed to know we would be worthy stewards, responsibly fulfilling its original intention.

In that moment, it was clear that Grail Leadership was finally ready to exist as a reality in this world ~ because I had shown myself that it is living, whole and intact, within the physical layers of my being.

Welcoming the Masculine Home

Photo by Jan Tinneberg

Along the twists and turns of my heroic journey, I’d thrown the wounded masculine out of the house ~ a necessary act to uncover and restore my exiled feminine. I’d even come face-to-face with the distorted masculine aspects of myself, healing ancient wounds with forgiveness and compassion. What I didn’t know is that I hadn’t yet fully welcomed the healed masculine back into the sanctuary of my home.

As I look back now, I can see it was my feminine who’d set this trifecta of tripwires.

Of course, “she” is me; and so is “he.” As much as it can be helpful to observe and analyze the feminine and masculine aspects of ourselves as if they were distinct, they can never actually be separated. “Me” is a co-creative dance of intimately intertwined polarities weaving their way into ever more life and evolution.

So, please humor me while I imagine the tripwire process from the perspective of my feminine….

She was afraid of letting the masculine back in too soon. Sure, he was saying all the right things; but he’d always been good at that and she’d been fooled before. Could she really trust him? She needed to test him, proving to herself that he could be trusted with this valuable treasure ~ the vision and mission of Grail Leadership, the expression of my genius.

Tripwire #1: Was he going to march back in, take the microphone and start spouting off intellectual concepts that don’t honor the relational spaces between them and their connection to the whole? Actually, it seems that he has been quite humbled by his journey into her realm. He realizes there is much he doesn’t know ~ and he now understands the vast difference between the mental realm of knowledge and the physical earthiness of embodied wisdom. Through his connection with her, he has come to remember that true north is only ever found in the orientation to the whole. He is clearly devoted to defending and maintaining the integrity of Grail Leadership in all its multi-dimensional wholeness.

Tripwire #2: After reveling in the boundless flow for years, was he going to come in and cover the whole thing in scaffolding and rigid structures, constricting it with the pressure of needing to get something out of it? It turns out that no, he was showing up ready to construct a framework that supports from underneath ~ no ceiling, no pressure, no need to limit or control, just a deep desire to serve the mission.

He was now bringing a critical piece that had been missing from Grail Leadership ~ the form of a container and self-selecting pathways that serve the evolutionary pioneers of our time, allowing them to understand this regenerative form of round-table leadership and choose how to access it in a way that is right for them. Not to mention the sense of safety and stability of riverbanks that help guide the flow, as we all navigate our way through this new realm together.

Tripwire #3: After a lifetime of domination, suppressing her in his attempts to survive, was he now going to capitalize on this genius, monetize and commoditize it, sucking the very life out of it? Actually no, he has truly learned that survival does not need to be purchased through making money, earning our keep, or justifying our very existence. He’s seen the cosmic joke that operating out of survival keeps us from truly living, with all of our energies focused on avoiding the inevitable truth of our physical dying. He has no need to seek power or control, as he’s tapped in to the source of incredible power that moves through his own being. He’s found the true abundance of being in connection with all life and in integrity with his mission ~ and, he’s learned much from her about receiving, knowing that we cannot give from an empty cup. And he would not do anything to sacrifice the freedom and vitality he has discovered through his connection with her.

I’m imagining her taking a deep breath, and saying “Well, he has passed all the tests I laid out for him. He now really knows me, appreciates me, and reveres me. And I adore his strength, intelligence and vitality. It won’t all be a bed of roses ~ after all, the thorns are a part of the adventure of life and growth. But we are finally in it together, honoring and cherishing the gifts of the other that so perfectly complement our own.”

What’s next?

Photo by Jack Anstey

The final stage in Joseph Campbell’s 12-step Hero’s Journey is called “Return with the Elixir.” This is when the hero returns to his community as a force of change, bringing healing and wholeness to society at large ~ offering hope, life, and purpose in people’s lives where it had once been lost.

Out beyond ideas of wrongdoing and rightdoing there is a field. I’ll meet you there. ~ Rumi

The hero’s/heroine’s journey is the archetypal story of our trek through the Separation Age, a process of synthesizing opposing polarities into integrated wholeness ~ at both a personal and a collective level. I have no idea what awaits us in this Beyond Field, but I am excited to explore this new terrain alongside fellow Grail leaders as we co-create the next archetypal story for an age of sovereign unity, abundance and mutual thriving.

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Holly McCann

Founder & Vision Keeper of Grail Leadership, helping pioneering leaders thrive by aligning core mission, essential genius and the regenerative flow of nature