Photo by Giancarlo Corti

Forgiving my Wounded Masculine

Freeing myself from a lifelong pattern

Holly McCann
Published in
12 min readJan 4, 2023

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I’ve recently emerged from a big initiation ~ navigating a threshold that I naively thought I had already crossed in the hero’s and heroine’s journey of my life.

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” ~ Steve Jobs

As I connect the dots of my experiences over the past two years, finally making sense of my trek through nine countries in four continents and two hemispheres, I can now pinpoint where I was in the archetypal heroic journey. Unbeknownst to me, I’d been moving through the phase known as the Healing of the Wounded Masculine.

This is the penultimate initiation in the quest for the Wholly Grail of Sovereign Unity ~ the journey of coming into a state of being where the feminine and masculine aspects are no longer experienced as being in opposition but as essential polarities that dance together in harmony, wholeness and vitality.

I want to share with you some of my unwitting pilgrimage to reunite with my healthy masculine. While the faces and places will be different, my hope is that you may find in this sharing some gems of insight, confirmation and camaraderie that may be helpful as you wind your way through the breadcrumb trails of your own epic adventures.

[For the first article in this three-part series, and to learn more about the genesis of Grail Leadership, read Restoring the Feminine to Birth a Whole New Vision]

The pendulum swing to the feminine

Photo by Harli Marten

After decades of leadership roles in the masculine world of business, I toppled into a dark night of the soul that turned my entire life inside out and upside down.

Emerging from that underworld journey, in which I reconnected with my long-lost feminine, I experienced such a sense of liberation and peace that I vowed I would never go back to the masculine ways of doing business.

I wound down my coaching practice. After all, how could I now hold myself out as an ‘authority’ on anything, given that I was continually questioning everything I ever knew?

I rejected all forms of marketing systems that I had previously used to great success ~ no more sales funnels, opt-ins, or online membership programs, and definitely no more “education-based marketing” approach of telling people that they had a problem and I knew how to fix it!

While I was passionate about new-paradigm models of leadership, I no longer wanted to be “the” leader of anything. All I wanted was to bring my leadership experience and wisdom to the round table, co-creating shoulder-to-shoulder with other visionary leaders who were devoted to making a difference in the world.

In late 2018, after taking on a series of roles supporting other transformational leaders, I birthed my own vision. This body of work known as Grail Leadership emerged through an extraordinary co-creation with two other pioneering women leaders.

After two years of swinging widely into the feminine, and not seeing as much traction and forward momentum as we’d hoped, we decided to take a step back to regroup. Not to mention, we were in the midst of the “year of Covid” ~ a year when the whole world seemed to be disoriented and taking a pause.

Connecting with the masculine

Photo by Wonderlane

Over the next few months, I jumped into an all-consuming project building a website and online education program for a non-profit organization where I served on the board of directors.

Shortly after completing that, in early 2021, I had the urge to travel internationally again. I was feeling really drawn all of a sudden to Costa Rica {and it happened to be one of the few places with an open border}. I had no real intention or plan, simply following what felt like a strong calling to go.

A few days after arriving, I felt rudderless, disoriented and lonely. What was I doing here? And why had I felt so called to come here?

When the heat and humidity started to get to me, I retreated to Mount Chirripó ~ the highest mountain in Costa Rica and the “land of eternal waters.” I spent a month there in a beautiful casita on a powerfully flowing river just outside of the national park, rejuvenating in the nourishing energy of the feminine.

During that time, a friend connected me to three men who were launching a start-up business ~ developing co-living and co-working centers that would evolve into regenerative villages through an innovative membership model with digital tokens. I was so inspired by our conversation that I flew to Guatemala and spent a month with them on Lake Atitlan, along with a group of their friends and potential co-creators.

I felt tremendous resonance with these men and their vision. The more we got to know each other and our work, the more we were blown away by the synchronicities and connections we had in common. And they were equally inspired and excited about Grail Leadership and all that I was bringing to the table.

They invited me to travel with them ~ first to a regenerative-focused gathering hosted by a mutual friend on a private island near Bar Harbor, Maine, and then to Baja, Mexico to explore a potential location for the first co-living/co-working site.

We spent a month in the searing heat of Baja, in a large beach house where I joyfully engaged in epic white-boarding sessions with one of the founders. We all spent every waking hour deep in the throes of ‘start-up mode’ and immersed in meaningful conversations about the world and the significant impact we were devoted to making. We also snuck in some fun and exercise in nature, as we held “Sea Brief” meetings every evening to catch each other up while treading water in the ocean!

At the end of our time there, they invited me to join their team as a co-founder. I had been checking in with my co-creators in Grail Leadership, and we all felt that each organization was the missing piece of the other’s puzzle. Grail Leadership was bringing the more feminine round-table leadership and ecosystem-based organizational models ~ and these men were bringing the more masculine capacities of distributed financing and regenerative building design and construction. A marriage made in heaven!

We moved on from the desert of Baja to the mountains of southern Ecuador, living in an eco-retreat in the village of Vilcabamba ~ an idyllic setting known by most as the Valley of Longevity {and by some as the “land of aging hippies”}. We were exploring this region as a location site and were thrilled to find not only the beautiful landscape and lower cost of living, but also the number of regenerative-minded locals and expats in this small community. I spent the next six months there, making amazing connections and continually lit up by possibility and potential.

Confronting the unhealthy masculine

Vilcabamba, Ecuador

After months of intense collaboration, I decided to take a step back from the group when I realized that my nervous system was consistently on edge. I was spending too much time working and “efforting” in the masculine ~ something I swore I would never do again. I was also locking horns a bit too much with one of the founders who was very much in the masculine. {Having swung so far into the feminine, I was quick to be triggered by anything in the opposite polarity.}

I had also begun weaving more deeply with a wonderful couple who owned a biodynamic farm near Vilcabamba with a vision of establishing a community there. They were very active in the area, working closely with local residents and with the indigenous Kogi tribe of Columbia who had identified their farm as sacred land. We shared very similar visions for collaboration and round-table networks as a way to make meaningful impact.

I attended inspiring retreats at their farm with Kogi elders (known as Mamas) and met several times with the founders as we envisioned ways to establish a regenerative community of people living on and stewarding this sacred land.

I was ultimately invited to join their team of people working to bring this vision to life. And I almost said Yes….

About that time, however, I was noticing that I was becoming very triggered in several arenas, reacting strongly to what I was perceiving as the imbalanced masculine on display all around me.

Experiencing my world through a hyper-critical and highly emotional lens, I felt I was surrounded by: men who were talking for the sake of hearing themselves speak, leaving no space for women’s voices; men boastfully beating their chests in what felt like competitive, alpha-male behavior; men insisting that they knew the answers, leaving no room for questions or differing perspectives; leaders who wanted to collaborate but weren’t willing to let go of control; and well-intentioned organizations wanting to teach the local indigenous youth how to start their own businesses in a very American-centric approach.

I had no tolerance for any of it ~ and I was harshly judging them all. I repeatedly broke down in sadness and anger over what felt like echoes of the masculine-dominant world I had left years earlier and to which I vowed never to return.

Forgiving my inner masculine

Photo by Ingo Stiller

Genuine forgiveness does not deny anger but faces it head-on. ~ Alice Miller

One evening, after retreating to my room in tears of frustration and anger, it dawned on me that there was a pattern going on here. I was being triggered by the masculine so often and to such a degree that I couldn’t help but take notice.

After some time spent in contemplation and journaling, it became painfully obvious that the common denominator in every scenario was me. Of course! {slaps forehead} ~ I was actually rejecting parts of myself that I hadn’t yet forgiven.

Reflections of my own distorted masculine were now coming up in my field like a cartoon character, taunting me at every turn, demanding my attention, and begging me to alchemize these wounded masculine energies that were finally ready to move out of my system.

In several tear-filled journaling sessions and a few sleepless nights, I was powerfully confronted by my inner toxic masculine ~ meeting head-on the aspect of me who had spent so many years attempting to control my life and those around me, thinking I had it all figured out and judging others who “didn’t get it”, and steamrollering over my own feminine.

Oof! After experiencing so many awe-inspiring qualities in my newly liberated feminine, it was extremely painful to come face-to-face with all the ways I had unwittingly abused and diminished her throughout my life.

As if that wasn’t enough, I was also encountering the ancestral and multi-dimensional facets of my being that had been doing this at a collective level for eons. {Since I’d opened that door, I might as well meet all the demons lurking in the shadows behind it!}

Finally, drawing on the compassion and grace of my restored feminine, I was able to clearly acknowledge, forgive and integrate these masculine aspects of myself that had become so distorted through their separation from the feminine.

Releasing a very old pattern

Photo by Leo Rivas

A few days later, I had lunch with a friend I’d met in Ecuador who was involved in these local initiatives. He had been witnessing what was happening for me and pointedly said, “You have such a clear vision of how things can be different. And you have what it takes to actually make it real. Why aren’t you starting your own regenerative farm and community?”

I felt the familiar resistance rise to the surface: “I don’t want to be the leader; I don’t want to take on responsibility for an entire initiative; I don’t want to build something on my own again; I don’t want to slide back into the same old patterns that had nearly squeezed the life out of me. Besides, I don’t think I’m meant to start one local initiative. I really want to be operating at the systemic level, generating a massive global impact.”

That afternoon, while contemplating our conversation, images of all the organizations and initiatives I’d been involved with over the past five years suddenly came flooding in ~ along with a dawning awareness. Oh no, I’ve been doing it again….

Just before leaving for Costa Rica, I’d noticed a pattern that had repeated itself in four different scenarios since I moved to Colorado: I would connect with fledgling organizations founded by leaders with a resonant vision for the future; I’d passionately jump in with both feet; I would even live with the founders, sleeping, eating and breathing the mission in an intensely intimate container; I would give it everything I had, contributing with little to no compensation ~ usually taking it on as my responsibility to find a way to bring in revenue so that everyone could be paid; and ultimately, I would walk away feeling depleted and disillusioned.

The only time I hadn’t operated in this way was in founding and co-creating Grail Leadership. Alas, as soon as I stepped away from it for a bit, I fell right back in to those deeply engrained behaviors.

While cleverly disguised in a more feminine mask of “co-creating new-paradigm organizations,” I was still employing the same masculine survival mechanism I’d developed at a very young age. The only way I knew to keep myself safe, to feel valued, and to avoid outcomes I feared was to work really hard and take on way too much responsibility for others’ well-being.

Ironically, my survival mechanism had become the thing I feared most. I was terrified of returning to my unhealthy masculine ways of overwork and over-responsibility. And yet, guess where I kept ending up….

Having moved through the showdown with my wounded masculine days earlier, I was now able to see this pattern so clearly ~ a sure sign that I had stepped outside of it. And I could see why it had continued to hang around.

This pattern was determined to keep replaying itself like Groundhog Day, with changes only in the faces and places involved, until I had seen my own shadow and finally learned the lesson it held for me.

The deeply engrained behavior of taking on too much responsibility and working too hard was stemming from ~ and fueled by ~ my wounded masculine. I thought I had left behind my old ways of overwork and over-responsibility, but my lifelong companion was still there ~ he was just cleverly disguised in a cloak of purpose-driven, evolutionary projects.

Truly healing the masculine

Photo by Mohamed Nohassi

Through my underworld journey into the feminine, I had peeled away many layers of armor and control, shifting out of countless misguided beliefs and imbalanced masculine behaviors. To me, this is what it meant to heal the distorted masculine.

It turns out I hadn’t actually healed my wounded masculine, I’d just kicked him out of the house. And he would keep coming back until I was ready to look him in the eye and see my own reflection ~ ready to see that I was still rejecting, judging and condemning parts of myself.

I could not resolve the relationship with my masculine by trying to cut him out of my life. This significant aspect of me would only be healed when the beauty had fallen in love with the beast ~ when I could clearly see him for what he was and make peace with him.

By acknowledging, owning and forgiving those ailing masculine aspects, loving them into wholeness, I came to understand what it really means to heal the wounded masculine.

In doing so, I’d resolved what was at the root of this enduring pattern ~ and was finally released from it.

Looking back now on the confusion I felt in Costa Rica about why I’d been called there, and all that’s transpired since, a smile of appreciation spreads across my face as I feel a winking nudge from Steve Jobs: “You can’t connect the dots looking forward!”

In perfect timing as ever, I returned from South America in late December 2021, having wrapped up this extraordinary phase only a week prior to my departure. Little did I know then that the reconciliation with my masculine was only partially complete.

Just up around the bend in 2022 lay even more dots ~ involving more international, cross-hemisphere travel ~ that would eventually join up to round out this epic quest into wholeness.

Ahh, the beautiful chaos of this life ~ and the clarity of order that eventually, inevitably appears in the rear view!

It would not be until the end of 2022 when I would realize that, while I had forgiven my inner masculine, I hadn’t yet allowed him back into the house….

[For the final phase of this journey, read the third article in this three-part series: Welcoming the Healthy Masculine Home]

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Holly McCann
Grail Leadership

Founder & Vision Keeper of Grail Leadership, helping pioneering leaders and their businesses fulfill their mission and thrive in alignment with Nature.