Which hat do I wear today? A Personal Essay

I’m Shiloh McCloud. Artist. Writer. Teacher. Entrepreneur. Revolutionary—depending on what hat I am on that day. Most days I am wearing my captain’s hat—which happens to be a cowgirl hat—at the helm of my sparkly pink ship, cruising around to different marketplaces, and ports of call.

Some days you’ll find me at the art gallery. On others I’ll be in my studio or at my writing desk. Still others I’ll be teaching sacred art or visionary business at a school or college. Many days I’m at Cosmic Cowgirls University (on-line or on-campus), paintbrush in one had, microphone in the other, inviting women to CREATE as if their lives depend on it.

Some creative’s don’t like to be labeled with titles, but since I’m always changing roles I find titles are like my hats. They support me in choosing when I am the art doctor or the den mother, and whether I need to serve up a cup of tea and compassion, or a healthy dose of kick-yer-ass git-er-done visionary wisdom. Choosing how I show up is part of my schtick. After all, I am the creator of my own legend, why not have a good time?

Folks often look at me and my endeavors with a quizzical, baffled, curiosity. They even ask how I got “this way”. It sounds part compliment, part accusation. I think what they really want to know is not how I got to be me, but how they can fast track their own lives to match a fuller version of who they are, or want to be.

From the time I was a little girl, I had loving support to be myself. For this I am most grateful, and consider it one of my assignments in life to share from that abundant encouragement I was given. One of the tools my artist-poet-designer mama, Caron McCloud, so carefully placed in my little toolbox—which I never leave home without!—was: perspective. She taught me how to THINK. How to put things into context. And how to live life as a Great Adventure. Most of the tools were to be utilized to indulge my creativity and to be original at all costs. My mom is still my best friend and ally, and to this day encourages me to NEVER give up on my dreams, or to give into my fears.

Growing up, we moved a lot. With each move she encouraged me to take advantage of being “the new girl in town” and re-invent myself. If I didn’t like the new me, well, we’d be moving on one day and I could try out another. It may sound kind of schizophrenic, but it wasn’t. I think most folks don’t get a chance to try out all their selves. We tend to settle into a self that is determined by other’s expectations, and all too often, end up leading lives that are not fulfilling. We neglect a lot of the juicy parts which only come out after a few glasses of wine! Not being ourselves is scary. It does not have to BE like that. We can be legendary, even if it is only in our own minds. We can work with what we have right where we are, and use it—even the pain—for our personal transformation.

I learned about the happiness of making art from Sue Sellars, my mentor and the woman who has co-parented me throughout my life. She taught me to put my intention into the work, to make it mean something, for myself and for others. Getting that part was one of my big wake up moments. From that point on HOW I created became personal medicine, a revelatory serum of grand proportion.

By the time I was twenty-two, I was coming down from the rage of teenhood, followed by disillusionment with the “system”, and feeling trapped within the patriarchy that defines the paradigm in which we live. I left the San Francisco, moved to the country and promptly had a mountain top experience. I experienced an intense awareness of the pain and suffering and greed in the world. This awareness created in me what I call my revolutionary heart, and a relentless perseverance to give. I believe that those who can serve, should, and from deep within myself, I knew I was called to serve.

It was at this time, that I first encountered the Blessed Mother, Mama Mary. She responded to my broken heart and tears. I felt that she told me that what was unique to me is CREATIVITY and that I must plant my “Tree of Life” in that creativity, and that through my art and poetry I would be led to guide and inspire others towards their own peace, creativity and life purpose.

I began to consider the possibility of being able to serve by being an inspiration for folks to be MORE themselves. And not just more of who they already are, but who they WANT to become. I could work with others to encourage them, that we can invent and re-invent ourselves.

After ten years of making and selling art, owning galleries and promoting women’s work, teaching, and creating and publishing books, I started feeling the frustration of the transitory “come and go” nature of business, and the challenging work associated with keeping up with all the ones doing the coming and going.

I felt there had to be a way to guide and work with women that was more productive and had more consistency…what I wanted was a movement! Through prayers to Our Lady, and profound ongoing conversation with my brilliant and gorgeous husband, Isaiah, I entered into a deep visionary space to contemplate the burning question: How can I be of service and make a good living, so that I can have the freedom to give as much as I want?

I came to the realization that I needed a tribe to create that movement with me. A tribe that would be sustainable. A tribe motivated by time commitments not framed in typical business hours. We needed something we could rely on over the years.

I knew it was put on the hat of leadership. This is where the cowgirl hat came in along with the handle “Chief Laughing Cloud.” I founded of Cosmic Cowgirls, a business with a 100+ year vision in which women’s wisdom is to be shared in a “circle style” community, connecting women across the world. Within just a few short years we have a nationwide membership base, a campus in Sonoma County, a University online, and we publish books and blogs relevant to leading lives of meaning.

In one of our courses, “Leading A Legendary Life,” we each paint a portrait of our invented legendary self, and write our shero’s journey. This gets us in touch with the ways we have not been “being.” Or sometimes we discover that we have been being legendary, but didn’t know it. Women are inspired and invigorated by being asked questions like: What medicine do you carry in your medicine basket? What tools do you carry? What does your magic cape looks like? What mountains have you scaled in the service of choosing to live a vital, creative, and yes! fulfilled life. While we are learning to paint and to write we are participating in a self-revelatory healing process, besides developing a personal creative practice that will serve us throughout our lives.

At Cosmic Cowgirls we also have a vengeance for independence. We are mindful that not everyone wants to be an entrepreneur. However, even if one has a regular job, one might want to try a little something on the side. We invite baby entrepreneurs and also seasoned ones, to meet us at the Big Dream Café, a virtual café for visionary entrepreneurs where we teach and support women to invent their lives in terms of business and/or projects by which they are inspired.

There is no grand ship without a crew. And one very important thing I’ve learned is the necessity of surrounding oneself with powerful folk—ones that are smarter-n-you in certain areas. Everything I do is made possible by the women and men who journey with me. I cannot say enough the importance of tribe, not just like minded folks, but your own tribal folk who “GET” you. This must be a part of the pursuit of every human, because isolation from being truly known by people you truly know can cause a lifetime of blues, besides being awful dang lonely.

Everybody gets their kicks different ways. Mine come from answering calls from the deep wilderness of womanhood. Tending the suffering in the world somehow, whether it be through extending the red thread, or coaching someone through self loathing into self honor, teaching intention based creativity, or serving up a cup of tea—this is my joy.

I live a privileged life. I know that – and that is why I am so grateful. I do what I love to do, and have peace in that process. Having joy and peace, however, does not mean that what I do is easy. Things haven’t always been smooth sailing. Far from it. I didn’t graduate from college. I don’t own a big house on a hill, I don’t have medical insurance, and I didn’t start out “talented” in art or writing or with a particular advantage other than I was supported by creative women. That is huge! And that is why I want to share it.

You know what? Just because I do what I love, doesn’t mean there aren’t plenty of hard days. I have to imagine my purpose, and then git on my red cowgirl boots and stomp around the yard a while, and then go to work. I am often undone with the pain and suffering in the world. It makes me want to get in bed with my blankie and my kitties, read a good novel, and eat mashed potatoes with lotsa butter. But I keep getting up and I continue to invent, improvise and innovate. And I continue to discover the fullness of my assignment on spaceship Earth. And regardless of what else has happened, I have steered the ship in the ways that are important to me and that reflect my values.

I don’t (as the saying goes) make art for art’s sake. I make and teach it to bring healing into the world. I truly believe that when we create, with an intention of sharing love, it works on a quantum level. I am not talking about “create our own reality” hoodoo—I believe there is a brilliant creator in charge of reality, but I also know that I need to show up so there is something for Creator work with in me. Showing up means thinking the thoughts that generate the love and then taking the actions consistent with the sharing of that love, and continuing that cycle consistently.

Any even semi-realized visionary wants to share their love with the world—let me rephrase that—cannot help but share their love with the world. Doing so becomes impassioned to the point of a healthy obsession. The pursuit of meaningful lifework in the grand marketplace of life is a fulfilling life path for me and for most of the entrepreneurs I know. We might be tired, lonely and sometimes misunderstood, but most of us are, for the most part, happy no matter what.

The desire to create and share my work with the world has me out, toolbox in hand, behind the wheel of the ship, cruising to the next destination with my cosmic compass set to: SERVICE. But on the days when I am free to do whatever I want to: I go to the art studio.

What I am working on now is everything I have always worked on, and I am also writing a new book, “The Legendary Teahouse of Lupe Max.” Writing this book is what I do to nurture myself as I build my various enterprises and projects. It helps me keep my hat collection in context through showing me that we creatives are diverse creatures, and just because we may not be able to do it all doesn’t mean we shouldn’t try.

My marriage is at the heart of my life, and everything that has been created is in collaboration and celebration with—besides Creator—my beloved husband of sixteen years. At this moment in my herstory it is early in the morning and he has brought me a cup of coffee and is playing his guitar. The day is dawning on my gratitude and sitting here writing this, I feel blissed out. We are about to have a visioning session for our life.

And so, there is liberation I find, in learning to be ourselves, and to discovering which hat to wear each day. In not limiting ourselves to one way of being, but including as much of who we are as we can.

Shiloh Sophia McCloud

Learn more about Cosmic

Learn more about Cosmic Cowgirls University