Photo by Tom Gainor

Restoring the Feminine to Birth a Whole New Vision

My journey of birthing Grail Leadership {and myself} into the world

Holly McCann
Published in
11 min readDec 31, 2022

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But little by little, as you left their voice behind, the stars began to burn through the sheets of clouds, and there was a new voice which you slowly recognized as your own, that kept you company as you strode deeper and deeper into the world, determined to do the only thing you could do — determined to save the only life that you could save. ~ Mary Oliver, from “The Journey”

For the first 48 years of my life, I lived solidly in the masculine. I was the oldest of four girls, taking on a great deal of responsibility at a young age when my parents divorced and my father left. I put myself through college and law school, and climbed the ladder of success through three careers ~ spending twelve years as a lawyer and the VP/General Counsel of a healthcare organization, twelve years as the owner of two award-winning stationery boutiques, and then as a leadership coach and consultant.

I created and managed a robust legal department for a rapidly growing corporation. I initiated and led multi-department projects that impacted the entire organization. I built from the ground up a best-in-class retail business with two brick-and-mortar shops and an online store. I managed teams and created operational systems to optimize service and profitability. I started businesses and wound down businesses. In the height of my entrepreneurial frenzy, I had five businesses with two in start-up mode at once.

I knew how to build and lead organizations in the masculine world of business, through the well-trodden pathways of the conventional. What I didn’t yet know was that I was here to pioneer an entirely new path of leadership ~ one that would require the restoration of the feminine, beginning with my own.

Dark Night of the Soul

It turns out that, when you sign up for a big mission, life has a way of moving mountains to give you the best chance of fulfilling it. You just have no way of knowing that is what’s happening when the tectonic plates start shifting and the ground beneath your feet disintegrates….

After repeatedly attaining heights of success in my careers, yet feeling miserably unfulfilled and on the verge of adrenal burnout, the walls of my carefully crafted house of cards came crashing down.

For the first time in my adult life, I was utterly failing, completely incapable of holding together all that was unraveling in my world. The streams of income from my lucrative coaching business had slowed to barely a trickle, my 20-year perfect marriage had run its course, and my mother who had played such an immense yet complex role in my life was about to lose hers to ovarian cancer.

Despite several stubborn attempts to stave off outcomes I could only see as catastrophic, “trying harder” and “working smarter” as I tried to bend nature to my will, I finally had no choice but to surrender to the impossible reality that I was powerless to fix any of it.

Photo by Tim Marshall

Freeing my Feminine from Exile

Tumbling headlong into the underworld realm of the feminine, I spent several months swirling in a sea of confusion and disorientation as everything I thought I knew was turned upside down. I was overcome by tidal waves of ancient trauma and pent-up emotions, dragged down by the suit of armor {that I thought was me} into an abyss of personal and collective grief so deep I wasn’t sure I’d ever surface.

As I shed layers of identities and beliefs that no longer fit, I began to discover troves of sunken treasure ~ dredging up parts of myself that were submerged so deeply I hadn’t even known they existed.

I came to realize the incredible grace and beauty that exists in the very same feminine qualities I’d disdained in others throughout my life.

I reclaimed the awe-inspiring magic and tremendous power that had lain dormant in the untamed wilderness of my true feminine nature.

In reconnecting with her, I remembered my connection to all life, true abundance, and unconditional love.

My inner masculine ~ who had valiantly built walls of protection so thick that they’d become a prison ~ could finally begin to let go. In the nurturing presence of compassion and forgiveness, he started to release his stranglehold of control and ease up on the relentless self-criticism, over-work, and over-responsibility.

With my feminine finally freed from her lifelong exile, I experienced a sense of liberation and peace unlike anything I’d ever known.

And I vowed never to go back….

Photo by Frank McKenna

Preparing the Womb Space

In the process of reclaiming my feminine, I moved far away from the masculine ways of doing business that had been my Zone of Excellence. {I would later find that I had thrown the baby out with the bathwater, but this was an essential part of my process as I created more space for my feminine to find her footing.}

I became passionate about whole-systems design, regenerative food & farming, and new collaborative organizational and leadership models that are more aligned with our rapidly emerging shift in consciousness.

I was moved by a deep desire to be in my Zone of Genius ~ bringing my leadership experience and wisdom to the round table, in co-creation with other visionary leaders who were devoted to making a difference in the world. I knew I had a role to play in new-paradigm leadership, but no longer wanted to be “the” leader of anything.

In 2016, I sold or gave away nearly everything I owned and moved across country to Boulder, Colorado. Within three weeks, I was hired as the CEO of a start-up company devoted to “an enlightened civilization by 2035”, which had been founded by a spiritual teacher. After six months, we amicably parted ways when it became apparent that he was choosing the path of the guru and my approach of co-creation turned out to be more about my vision than supporting his.

Almost immediately after leaving that role, I immersed myself in an inspiring project to purchase in collective stewardship a very special retreat venue on sacred land in the foothills of Boulder. This led to several additional collaborations, all focused on co-creating regenerative communities as part of healthy ecosystems.

In late December 2017, I was invited to lead the systems and operations of an organization dedicated to personal transformation retreats, centered around somatic trauma release and self-leadership. So I put my belongings in storage and moved to the island of Gran Canaria to live and work with the founder. Again, after about six months, we parted ways when my co-creative approach was not actually aligned with supporting the vision held by the founder.

In a tear-filled conversation, my highly intuitive friend Dawn said “You have a multi-dimensional vision that is bigger than anyone I know. You need to stop trying to support other people’s visions and just write a book about your own!”

Despite her supportive urgings over the years, I had been resistant to writing a book. In this rapidly emerging space, I didn’t want to write something that would be quickly outdated. And I didn’t want to just sit back and dwell in the conceptual realm ~ I wanted to be actively engaged, prototyping new trails through this exciting shift in ages! But I was beginning to open to the idea.

Synchronistically, a few days later a dear friend invited me to stay with her in Winchester, just outside of London. She was offering a beautiful en-suite guest room in her new home, where I could focus on documenting the many maps, models and visions of whole-systems leadership and organizational design that had been brewing in me.

That trip turned into a highly activating journey through England, Scotland, Ireland, Italy and northwestern Greece over the course of five months. While every step contributed to the gestation of the vision I was carrying, in ways I wouldn’t fully comprehend until later, I spent exactly zero time putting pen to paper.

Photo by Mark Basarab

Laboring through the Birth Canal

Upon my return to the US, I retreated to New Mexico to spend a month alone on a mountaintop with the sole intention of writing. Those visions that had been dancing in my head were now bursting at the seams of my skull, demanding to be expressed!

This task proved to be far more challenging than I’d anticipated. The designs for holistic, regenerative organizations were so clear to me when they were residing in my system as whole and complete packets of energy. But as soon as I tried to reduce them to writing, they became immense, multi-dimensional concepts that seemed impossible to compress into any sort of coherent written form.

After many unsuccessful attempts that ended in tears and frustration, and several long phone calls with close girlfriends, I cried to my friend Dawn, “I don’t know if I can do this. I feel like I’m trying to give birth to an octopus while riding a whale!”

She laughed and said, “Of course you’re having a difficult time. You are so used to the masculine way of creation, where you have a vision for a business and then you go and build it. This is something entirely different. You’re now creating from the feminine, which is not logical or linear ~ giving birth is messy!”

My time in New Mexico would end shortly after my birthday, so I used that to set a deadline for myself. Determined to write something by my birthday, I finally published my first article ~ The Hero’s Journey of Grail Leadership: Finding the Wholly Grail of Sovereign Unity ~ ten minutes before midnight on December 12, 2018.

The conception of Grail Leadership had moved out of the ethers to take form in this physical realm. The baby had been born and was now its own living, breathing entity ~ one that no longer existed only within me.

The Infancy

I soon realized that the three women who had spent so much time with me on the phone throughout the previous month were like the midwives of Grail Leadership. Each a maverick leader devoted to new ways of living and leading, they were incredibly resonant and supportive of this vision, wanting to see it as a reality in the world.

I invited them to begin meeting as a group in weekly Zoom calls to share our experiences that all seemed to be strangely related.

So began a nine-month journey of profound connection, transformation and co-creation unlike anything any of us had ever experienced. As we shared what we were experiencing in our personal lives, we sensed important themes that were arising not only for us but in the collective as well.

And we went deep. Vulnerably sharing in this safe space of compassion and non-judgment, we were generating a field of unconditional love and nurturing that was incredibly healing and inspiring.

We were continually in awe. Not only were we experiencing rapid metamorphosis within ourselves, we were also witnessing the development of Grail Leadership as new concepts and patterns emerged in perfectly timed layers through this powerfully generative space.

I started taking notes as we realized that Grail Leadership was providing us with a new “lesson” each week, teaching us through direct experience what it really means to lead from an integrated place of wholeness, walking us through the many initiations of alchemy and healing that would be required of the pioneering leaders who are here to truly co-create a mutually thriving future.

The Toddler Stage

In September 2019, exactly nine months after I published the first article, we launched the Grail Leadership website to connect and co-create with leaders of regenerative initiatives devoted to serving the Earth and humanity. We created a free online community and began sharing some of what we’d been learning, sensing and experiencing about round-table leadership.

We began holding weekly community calls on Zoom, open to anyone who wished to join ~ providing a space for people on this journey to feel seen and appreciated in a warm, nourishing environment as we explored themes around personal and collective leadership that were arising for us each week.

It was beautiful to see so many people from all corners of the world who were powerfully drawn in, coming together, connecting with each other, and experiencing for themselves the power of this nurturing field.

The Awkward Adolescence

We were all about doing things differently than the conventional approach to business and leadership. We didn’t have a mastermind or a workspace, we had a ‘playfield’. We had no framework, no real structure or direction, and no defined pathways for people to access the principles and values of Grail Leadership.

We were simply going with the potent flow ~ excited to see what was emerging, and continually blown away by the magic and mystery of it all.

In September 2020, after a year of hosting our Weekly Weaving community calls and experiencing Ronacoaster-induced-Zoom-fatigue, we felt it was time to take a step back and regroup. We were excited to convene round tables of regenerative leaders, but we weren’t seeing people stepping forward with progressive initiatives who were ready to co-create in the way we’d hoped.

As with every teenager, we thought we had it all figured out and were “all grown up.” We thought we were providing a living example of a new-paradigm form of holistic leadership, where the feminine is harmoniously integrated with the masculine in sovereign unity.

What we couldn’t see at the time is that, in creating lots of space for the feminine, we had actually swung the pendulum far away from the masculine. This pole shift led to us experiencing the shadow qualities of the imbalanced feminine ~ over-giving, weak boundaries, and a lack of clarity and direction.

Of course, nothing ever happens “by mistake” with Grail Leadership. This was an essential phase of the process ~ we were continuing to cleanse our systems of deeply-rooted conditioned patterns of the distorted masculine, while getting more comfortable in giving free rein to the feminine.

Photo by Nick Fewings

Being the Change

“Be the change that you wish to see in the world.” ~ Mahatma Gandhi

Cliches often contain some of the deepest truths, don’t they?

As the feminine awareness of interconnectivity is increasingly restored in our reality, we are being shown that new-paradigm initiatives {those that are part of co-creating our flourishing future} cannot be built “out there” ~ they must be birthed through us.

As evolutionary leaders, we are the vessels for our visions, the portals through which our creations are woven into the fabric of our mutually thriving world. They become reality as they come alive within us, as we fully embody and be the gifts we are bringing to the world.

It now makes perfect sense that we took a step back, feeling a bit stalled. We had more to alchemize and integrate within ourselves before we could authentically radiate the wholeness that is at the heart of Grail Leadership.

We still needed to move through a critical phase in the heroic journey into sovereign unity ~ the Healing of the Wounded Masculine.

While we naively thought we’d already completed this phase, Grail Leadership knew better. It turns out we hadn’t truly healed the wounded masculine ~ we’d simply kicked him out of the house….

[To read more about the next phase of this journey, see the second article in this three-part series: Forgiving my Wounded Masculine.]

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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