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Connecting Within to Connect More

An Interview with Molly Caro May, Writer/Teacher/Speaker

In life, we have the opportunity to tap into our inner selves and explore. Some people do this, some do not. But the beauty of learning, listening, exploring is that we can make connections far bigger and deeper than ourselves. Molly Caro May has a powerful approach to leadership and to connecting within, to others, and to the universe at large. Ready to hear more?

WeInspireWe: Hi Molly – so great to meet you. We would love to learn more about you!

Molly Caro May: Absolutely. As you know, I am Molly Caro May and I am a writer, a teacher and a speaker. I have written two memoirs (The Map of Enough and Body Full of Stars) and I create and facilitate writing and story workshops both in person and online. I also work as a writing coach for anyone working on short or book length projects and have been working in this space for over 10 years. I am personally very inspired by the mountains, gardens (anything related to plants), travelling to foreign countries (I grew up abroad until age ten), minimalism, exploring any place on foot, art, somatic experiencing, and movement as connection to spirit.

WIW: You seem so down to earth (pun intended) Molly. If you had to summarize yourself, how would you tell your story of who you are at the core?

MCM: I am a fierce truth-teller and also tend to be mediator or peace-maker in many situations. These two parts of me work in equal proportion.

WIW: Tell us a little bit about the path that has gotten you to be the strong, female leader you are today.

MCM: It’s long and winding. I’ve worked in many settings: fruit-picking alongside men from Asia, working with at-risk teens in New Mexico, editing and learning the publishing and relatively fancy world in mid-town Manhattan, starting my own workshops from scratch in Montana, choosing not to get an MFA but to create the experience in a scrappy and dedicated way. Now, I’m an entrepreneur. I work for myself charting my own path, without any prescribed way to follow. This path is what has built capacity in me.

WIW: So many unique opportunities and time to select what matters most to you. How did or does that tie into your personal leadership style today.

MCM: I lead with care and listening and also directness. I like to make myself human in front of people. I also like to drop what feels like absolute truth when it matters and is authentic. I’m fun and serious and very much attuned to the energy in a room. This has helped me to evolve over the years too – especially in my ability to riff or go off script when needed. For me, it’s important to plan and envision a workshop or meeting or talk, and then I leave it up to the wind, literally. I’m quick to make changes as needed and I’ve gotten very comfortable in that by-the-second flow. Having both the plan and the flow has been integral to how I operate.

WIW: Can you tell us about a time that you had a major “aha” about the leader you wanted (or want) to be.

MCM: Over the last few years, I have REALLY clicked into a rhythm of being, where I am comfortable with defeat and failure and then rising again. I weather disappointment (professionally at least) really well and I have an eye for the long game. I also know that I’m not for everyone and really no one is for everyone, so I’ve dropped the people pleaser part of my younger self. I also trust pacing—that not every week is a “go” week, that there are fallow times and these are essential for creating anything. That is something I try to impart and share with my students and anyone I’m working with. Trust your own way.

WIW: Really listening to yourself and learning along the way is a theme I am sensing with you. What has been your biggest learning lesson as you’ve established your personal leadership style so far?

MCM: It’s possible to be many ways. We don’t have to fit into a stereotype. I can be both serious and playful. It’s also an art—knowing when to watch, observe and let a moment unfold vs. when to step in and steer. I like that dance.

WIW: How would you like to see your leadership style evolve in the future?

MCM: Right now, I’m in a moment of wanting to be the kind of leader who laughs and cries easily but still stays grounded. I can do this in some settings and not others. It’s a growth edge for me.

WIW: As you’ve continued to grow and explore, can you share with us any particularly difficult leadership situations and how you handled it (and if you feel like that situation differed because you’re a female leader)?

MCM: This is a common one I experience in my workshops. A student will be giving feedback to another student with a very well-meaning tone. In the process s/he might spout a stereotype (for example, “we all know fathers don’t do as much as mothers”) and, at that point, I have to step in, with kindness and gravitas, to invite us all to look at that stereotype and examine why we have it and whether it’s true. It’s a fine balance to do so without shaming that student and with bringing us into a field of “we are in this together to look at our language choices and evolve them.” It’s about forging community and connection. I do this, often, by observing my own language out loud in front of everyone. Oh look, I say “you guys” again; that’s a hold-over from my teenage years and let’s discuss. It’s hard to call someone out. It’s also essential. I want to be called out myself. I try to make it feel like an honor to have that learning given to me, and given to others.

WIW: When I say “female leadership” or “women in leadership”, what does that mean to you?

MCM: This is hard to answer. For me, it is how it should be, how it has been in ancient times, how it actually has been in times when people thought women weren’t leaders. Women have always been leaders. They have always influenced men and their decisions even when they themselves didn’t have decision-making power.

It’s a dynamic time for this sort of definition. For many years, it meant a woman taking on masculine (by masculine I mean masculine not male) traits in order to align with a cultural expectation. But now, it can evolve. My definition of female leadership is someone who is interested in and devoted to cyclical rhythms and uses them to run her life. She is all of the above. She isn’t just intense or just soft. She embodies the range and has a laser ability to use the right tool in the right moment. She is NOT always on, or always doing. She knows the value of pleasure and leisure as much as she knows the value of hard work. It’s a both/and thing.

WIW: What do you believe we need to do as a collective to allow for female leaders to thrive?

MCM: We females need to pull each other up, show solidarity and communion instead of competition. It’s also systemic. We need to create environments where different leadership styles work.

Women struggle with the age-old “if you are strong, you are a b@#$%.” We, as a collective, have been conditioned to be nice. And men have been conditioned to expect us to be sweet and available and willing. When women push against that expectation all hell breaks loose, in a good way of course. The only way to solve that challenge is to do is more, to do it enough that it becomes normalized. And to show the full human beneath the woman. She can be kind and strong as fuck. They aren’t mutually exclusive.

WIW: YES! Finally, Molly, any advice that you’d give to a young female employee beginning to develop her leadership style.

MCM: Watch other females around you and notice what you are drawn to, what resonates and experiment. It’s about practice and failure and more practice and success and on and on. Become a collector. You get to create your own mosaic. You don’t have to be like anyone else. How do you blend with your industry? Notice also what other people appreciate in you? They might be onto one of innate gifts and ways of being. Cultivate that. There’s only one you in the world. We need you.

Thank you so much for sharing your story with us Molly. You clearly are very blessed with gifts of sharing your voice, encouraging others to do the same, and allowing others to explore in the process. Your heart for opening others minds is inspiring and we thank you for all you do for the community around us!

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