We’re breaking down to break through.

Regenerating Leadership is a weekly newsletter, podcast and connection hub for visionary pioneers and changemakers ~ leaders like you who are:

  • done sacrificing the well-being of yourself, others or our planet in a relentless pursuit of success and growth at all costs;

  • focused on moving beyond merely surviving into thriving; and

  • called to make a meaningful impact in the world.

Whether you are an entrepreneur, business owner, corporate or community leader, you have come to realize that the ways we’ve been living and working are not sustainable.

As leaders, we are facing a confronting truth: that our conventional business models are inherently extractive. With a primary focus on profit and growth, we are incentivized to get the most by giving the least.

Operating under this definition of success, we are left burned out and utterly unfulfilled. In the process, we are burning out our employees, trading partners, communities, and the planet.

And it’s all coming to a head. Every day, we’re seeing our global systems and structures collapsing under the weight of these same unsustainable models.

But here’s the thing: we are in the midst of a metamorphic breakdown that inevitably precedes the breakthrough. And it’s happening at every level of our civilization.

“Everything will be all right in the end. If it’s not all right, it is not yet the end.”
~ Deborah Moggach, The Best Exotic Marigold Hotel

The systems and structures that extract resources at the cost of life are breaking down to make way for the new that is emerging ~ thriving ecosystems that generate more life for the whole and everyone in it.

That’s why the leaders of our emerging future are focused on regenerative, not extractive, leadership.

What is regenerative leadership?

Hi there, I’m Holly.

After achieving heights of success in three careers – as a lawyer & corporate executive, as the owner of award-winning retail boutiques, and as a business coach & consultant – I was burned out and profoundly unfulfilled.

I would often hear things like “How do you do it all so successfully?” But inside, I felt like a failure, never living up to my ideal of the perfect leader, mother and wife ~ and wondering what was wrong with me that I couldn’t just be satisfied where I was, continually seeking happiness and security at the top of the next mountain or at the top of my next career.

In 2014, the carefully constructed house of cards that was my “successful life” came crashing down around me. I entered an epic Dark Night of the Soul and tumbled into an underworld journey that would last nearly two years ~ one that stripped away all the layers of who I thought I needed to be in order to succeed and survive.

Finally, in the deepest darkest recesses of a dungeon surrounded by a moat and guarded by a fire-breathing dragon, I began to unearth the buried treasure of my true self ~ the one who I had exiled so long ago and hidden so well that I didn’t even know she existed.

In looking back and connecting the dots of my life, I could see that I came here to deeply explore leadership ~ through many direct experiences of what worked and what didn’t ~ and to pioneer new ways of leading beyond success-by-sacrifice.

So in 2016, I set out on a quest in search of ways to lead differently. It turns out I was also on a journey to recover my exiled feminine, to heal my distorted masculine, and to integrate these life-generating polarities so they can dance in harmony rather than warring in opposition {an ongoing work in progress!}.

This pursuit has taken me to twelve countries, four continents and two hemispheres over the past seven years as I’ve immersed myself in a variety of purpose-driven regenerative initiatives ~ working and living with the leadership teams of evolutionary organizations devoted to a flourishing future.

And, for the past four years, I’ve been co-creating and prototyping something called Grail Leadership ~ exploring ways of working within and across organizations in round-table ecosystems that are rooted in universal principles of nature and mutual thriving.

Why Regenerating Leadership?

Throughout all my travels and explorations, one thing is clear:

We are not meant to do it alone.

We are coming to realize that the world in which we live is a vast network of interconnected ecosystems within ecosystems. Thriving happens as we cultivate more nourishing relationships with ourselves, each other and nature.

We are being called to transform our systems and structures to more collaborative models that allow us to tap into the vast intelligence of the natural world and the wisdom of the collective.

At the same time, we are being called to transform ourselves ~ moving beyond the drama & trauma that keep us separate, stuck in old patterns of control and power distortions ~ so that we can actually come together to work effectively and sustainably within and across our organizations.

That’s why I’ve started Regenerating Leadership. I wanted to create a space of connection where we could discover, share and practice ways of leading ourselves and our initiatives differently ~ ways that allow people to bring all of who they are to the table and engage the passion, genius and vitality that lives within; ways that support individuals and organizations to make their desired impact and thrive.

Why subscribe?

Regenerating Leadership is a platform for exploring new ways of living and leading as we transform ourselves, our initiatives, and our planet.

Most importantly, it’s a space to connect with people who get your world and what you’re going through ~ because they have been there, are there, or are about to go there.

Subscribe to get full access to the newsletter, website and more. Never miss an update ~ every new edition of the newsletter goes directly to your inbox.

What’s here for you

Regenerating Leadership features for all subscribers:

  • ✍️ a weekly newsletter where I share my experiences, ideas, visions and questions around regenerative leadership ~ with as much authenticity, transparency and vulnerability as I can bring at the time;

  • 🎙️ podcast conversations {at least monthly} with leaders who are regenerating themselves, their initiatives and the world around them ~ sharing not only hope and inspiration, but the challenges they’re encountering and how they’re navigating them;

  • 💬 discussion threads where you are invited to share your reflections and experiences, engage in conversations, and bring your voice to the party; and

  • 🌱 whatever else emerges through this space as it grows and evolves

Consider this

If you resonate with what I’m sharing, please consider joining as a paying subscriber. Not only will you get to experience the joy of contributing to something you care about, you will be generating a wave of encouragement and support for my work and for other leaders in this community, which will be returned to you exponentially.

As a paying subscriber, you will also receive:

  • 🦋 excerpts from my breakdown-to-breakthrough journal entries ~ your backstage pass into the messy, juicy bits of my own transformational initiations!

  • 🔥 invitations to Hearthfire Calls ~ monthly gatherings online for paid subscribers

  • 📚 access to the archive of all previously published articles & newsletters

Want to give and receive even more regenerative goodness?

By joining as a Founding Member, you will generate a wave of tremendous encouragement, support and flow within this space that will be returned to you exponentially.

As a Founding Member, you will receive full access to everything provided in Regenerating Leadership.

Plus, for a limited time, I’m offering a complimentary 60-minute private mentoring session with me {normally $333} for you early adopters.

No matter what you choose, I hope you will read, listen, reflect and engage. I appreciate you and all that you are bringing to the world!

You are not alone. Pass it on….

The journey of leadership can be a lonely one, especially if you are on a mission that’s calling you into ever greater transformation.

This is a space where you can connect with other leaders like you who are:

  • sharing our big visions, our personal challenges & triumphs, and our wisdom;

  • unleashing our innate gifts ~ the ones that the world is crying out for and that we’re each uniquely designed to contribute; and

  • supporting and celebrating each other as we pioneer new pathways ~ regenerating ourselves as we regenerate the world.

If you like what you see here, please help our community grow and thrive by letting other leaders know about this space.

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A space for leaders who are moving beyond the success-by-sacrifice model and exploring ways to generate more mutual thriving for ourselves, our organizations and our planet.


Former lawyer, corporate executive, business owner and entrepreneur passionate about transforming leadership for an emerging world. Whole-systems visionary. Coach for purpose-driven entrepreneurs & executives.