If belonging is our birthright, how did it come to be that so many of us know so little about creating and nurturing deep connection and sustainable relationships?

Here we are, fully grown humans, having somehow missed out on foundational skills, practices, and perspectives that support us in choosing right relationship with ourselves and one another.

The important conversations we need to have sit and fester.

In our desire to stay connected, we grasp at familiar habits.

  • We ignore, dismiss, or try to fix other people (or ourselves).
  • We act tougher or more helpless than we are.
  • We expect our partners to “just know” what hurts or pleases us, and feel frustrated and justified in our belief that we shouldn’t have to ask for what we want and need.
  • We hold our tongues and seethe silently at serial boundary-steppers so others won’t see us as angry or unkind.
  • We beg for or demand attention and validation where there is none to be had.

We pretend we’re not hurting. We pretend we’re not scared. We pretend we’re not disappointed. We pretend we’re not powerful, amazing, talented, brilliant. We pretend and pretend until we can’t pretend anymore, then we lash out and say the things we really mean… but maybe didn’t mean to say quite like that.

We shun, we rage, we withdraw, we chase. We attack, we defend, we avoid, we control. (And this is the short list.)

We come by it honestly. We learn what we live.

Supremacy cultures teaches us that strategies like punishment and reward, withholding affection, blame, manipulation, violence, either/or thinking, defensiveness, retaliation, and rescuing—to name a few—will somehow “earn” us the closeness and harmony we yearn for, then we end up wondering why our best attempts at right relationship leave us feeling frustrated, bitter, confused, conflicted, ashamed, disappointed, bored, angry, or resentful—and ultimately disconnected.

Here’s the thing: we are connected. We are in more relationships than we ever thought possible. We are in relationships with ourselves, our bodies, our needs & desires, our parents & children, our clients, our communities, work, play, home, ideas, information, the cosmos, difference, life, death, time, money, government, technology, food, history, ancestors, art, pain, medicine, humanity, gravity, nature… literally everything (including our intimate partners and closest loves).

REGARD is a year-long, paradigm-shifting deep dive, small-group coaching space, community of practice, and 1:1 coaching container for humans who crave deeper connection and more authentic relationships — with themselves, the people they love, their communities, the world, and everything.

In this year-long conversation, we’ll explore the challenges that arise in our most important relationships… without bypassing the contexts, constructs, and systems of power that we inhabit together, and without dismissing the innate power and responsibility we have when we show up truthfully as who we are and with what we have.


In REGARD there is space to explore and practice the relational skills of:

    • Identifying and interrupting the places where dominant culture impacts how we show up in relationship
    • Telling the truth about what we want and need
    • Recognizing consent & honoring boundaries (ours and others’)
    • Navigating conflict and difference without compromising our integrity
    • Confronting our mistakes without spiraling into shame 
    • Repairing relational harm and returning to harmony
    • Generously acknowledging and cherishing the people and communities we love (because we want them to thrive, we want them to know how we feel, and most of them are not mind-readers)

This group is a space for asking tough questions about how we were taught—and not taught—to relate, for facing the honest answers, and for cultivating the skills and capacity to:

    • Bring courage, care, capacity, and skill to uncomfortable conversations
    • Recognize, confront, and dismantle oppressive beliefs and behaviors in ourselves and in our relationships
    • Show up with integrity and grace in our most important—and sometimes most challenging—relationships (because we can do this, for ourselves, for each other, and for the world we want to create together)

This is what I want for us: more joyful connection and less suffering in all of our relationships.

Hi! I’m James-Olivia. I am a friend to humans who love and lead, a facilitator and enthusiastic advocate of uncomfortable, extraordinary, life-changing conversations, a foundation shaker and root nourisher, and fellow work-in-progress (i.e. avid & grateful maker of mistakes).

I ask exquisitely rude questions & I cherish exquisitely honest ( sometimes squirmy) answers. I find this both fun and world-altering.

I believe the conversation is the relationship, and that in Right Relationship there is room for us (you and me and everyone) to show up with our whole selves. I believe neither freedom nor joyful connection can be sustained without combining relentless compassion with the disobedient inquiry.

In my own life and in my work with individuals, partners, teams, and organizations, I actively seek out and engage in the conversations that radically alter our most important relationships  — with ourselves, our loved ones, our work, the world, and everything.


What Regard ISN’T.
This exploration of Right Relationship…

    • will not teach you how to transform someone else’s behavior. Manipulation, coercion, and control are generally ineffective strategies for creating just and sustainable relationships. (We may, however, have a few laughs noticing—without shaming ourselves—where we try our relational fuckery.)
    • is not a space where judgment, shaming, or punishment are employed as teaching tools. You will be both supported and challenged to examine your conditioned beliefs, and you will not “get in trouble” for making mistakes, taking care of yourself, or not knowing all the answers (they’re your answers… you’ll get to know them in your own time).
    • will not neatly answer all of your questions. In fact, you’ll leave with new and different questions to explore. (Yay!)
    • is not a comfortable or safe space; it’s real life. Things get messy in real life. Differences are inevitable… and we can navigate the discomfort together with grace and care. Uncomfortable doesn’t have to mean painful, and messy doesn’t have to mean reckless. Regard is a space for exploration, growth, learning, practicing, taking responsibility for what is ours, and holding others capable of taking responsibility for what is theirs.
    • will not bypass the systemic realities of supremacy culture. If you are unready or unwilling to share in frank conversations that explore identity, socialization, systems of oppression, privilege & marginalization, and how these things impact our interpersonal & collective relationships, please consider joining us at another time. If you are willing but kind of uncomfortable, welcome to the conversation!
    • is not a support group (although I welcome and encourage supportive, loving humans to join each other here). Support groups provide a space for people to share personal experiences, feelings, and coping strategies. While acknowledging your lived experience is a crucial element of your experience in Regard, having the group hold space for emotional processing or lengthy personal stories is not its intended function. We will focus less on what happened, and more on what now?
    • is not a space for excavating or processing trauma. This bears repeating: in our conversations differences are inevitable, and our nervous systems may get activated. There is abundant room for us to be present with each other in difficult moments. And… If you are unable (or unwilling) to take care of yourself in the presence of your own or someone else’s discomfort, difference, or tension, this is not the space for you.

What Regard IS: a year-long commitment, a relating skills intensive, an experiential exploration of right relationship, group & 1:1 conversation, and a community of practice.

  • July 2022 through October 2022: Relating Skills Intensive (6.5 days over 4 months)
  • November 2022 through June 2023: community gatherings – twice each month (on Wednesdays 12-3pm ET)
  • Monthly 1:1 conversations with James-Olivia
  • Regular 1:1 conversations with a permanent program partner
  • Ongoing monthly community of practice (open to skilled clients, past and present)
  • Intimate group – up to 8 humans
  • All gatherings are live via Zoom and are not recorded
  • Cost: $8,500-$11,500

“Thinking of you and smiling face and heart.  Thank you for how you’ve influenced and shaped my life and relationships.  It hasn’t been easy or pleasant to make some of these changes and I am beginning to taste the sweetness of more truthful, reciprocal relationships.” —Anakha Coman

“Working with James-Olivia has truly been a GIFT. To be loved, held, mentored, and challenged by them has been powerful and deeply healing. Through their witnessing and guidance, I have strengthened my relationship with myself, my will/power, and my community. I’ve learned to lean into conversations and situations with more love, awareness, regard for myself and others, and possibility. They embody love, liberation, and leadership in ways that have given me so much inspiration, hope, and another way of being in this world. I’ve cultivated joy and embrace for my full humanity more. And I will forever be grateful. In a culture that benefits from your suffering and disconnection to Self, Regard and Disobedience School are a gift for your soul and the world. —Michelle Morales

“I feel more loving, connected, and capable of navigating through Life with ease and grace. They tenderly invite me to consider different perspectives, without ever coming off as judging or shaming me. The way they reflect my complexities back to me, with nuance and context, so I can better understand my Self, as well as my relationship with everyone and everything around me. The way they hold loving patient space while I process and uncover new layers of my Self. I have never felt as held and loved in my discomfort & growth as I have by James-Olivia. I cannot speak highly enough of them as a facilitator, teacher, guide, and human.” —Nic Strack

Uuuummmmm. I love James-Olivia too, but I also strongly desire to role a huge blunt after REGARD some days.” Rev. Ladale Benson

“James-Olivia is who you want to work with when you want to be LOVED, HEARD and GUIDED into understanding the intersections of disconnection we’re ingrained in — fully and deeply. They are incredibly gifted at listening to the experiences of your life and helping you dissect and dismantle the lies of limitation and cultural programming that separate you from moving towards embodying your realness in our society.” —Ash Johns

“James-Olivia creates ease, a sense of trust (because you know they will be honest), holds space for complexity and inspires connection and openness. It’s no wonder their sweet spot is around healing and deepening in relationship. They live and breathe it. In a field of coaches/healers/spiritual people holding space for radical transformation (which necessarily includes the examination of how we exist and choose consciously in systems and structures of privilege and oppression) they are someone who models integrity in leadership. I’m thrilled to have been introduced to them.” —Nancy Guerrera

I love that James-Olivia brings a strong anti-oppressive framework to their coaching practice, and the many ways that they consistently link the personal to the communities and systems we are all a part of. While I can always count on James-Olivia to be loving in our conversations, it is a love that is committed to truth telling and accountability; I know that I will leave our conversations understanding myself, my relationships and my social conditioning more thoroughly, whether or not it’s pretty. But James-Olivia is utterly unconcerned with pretty, which creates the space to actually just BE and make aware, sovereign, clear decisions about who we are constantly becoming. I can’t think of a bigger gift.” —F.C.