An Interview with Akaya Windwood, Rockwood Leadership Institute


This interview is the seventeenth in our series, Black & Bold: Perspectives on Leadership

Akaya Windwood, President, Rockwood Leadership Institute

Courageous. Visionary. Resilient.

Twitter: @rockwoodleaders and @akayawindwood



If there was a headline for your leadership journey throughout your career, what would it be?

Trust the path.

I used to believe…and everyone is taught to have a 5-year plan, a 10-year plan — to set up all these goals and benchmarks and then work according to the plan. I have found that that’s actually nonsense. The minute I set a plan the universe conspires to disabuse me of it. I came to understand that my planning was a way to manage anxiety as opposed to allow for possibilities that I couldn’t imagine. When I stopped planning and started creating wonderful, compelling visions for my work, life got much more interesting. My work became much more satisfying and I became much more effective because I stopped trying to control what was my life path and just started showing up for it. So, the headline would really be: “Don’t plan — trust the path.” (Akaya Windwood pictured at right. Photo credit: Susan Freundlich.)

What are some of your career highlights?

There are so many. Being selected as an American Field Service exchange student to Italy when I was 17. Discovering that I was a lesbian and falling in love with women writ large. Doing all the liberatory work around, you know, queer rights, women’s rights, farm workers’ rights, and that began – (I was young — in my teens and early twenties) the work of social transformation, though it wasn’t called that then. Getting radicalized as a result of some deep race and class oppression at UC Berkeley in graduate school. Starting my own business as a consultant around issues of inclusion and diversity and then shifting to leadership.

Coming to Rockwood, joining Opportunity Collaboration, and falling in love a lot all along the way. And when I say in love, I am talking about love of nature, love of the mountains, and the cycles of life. I’m in love with humans…in love with the magic. How astonishing it is to be alive even in the most challenging of times! I’m in love with aliveness — what a gift.

Those highlights certainly represent a continuum. I’m curious about getting radicalized at UC Berkeley. Can you say more?

I was the first kid in my family to go to college. So it never occurred to me or anybody else that I would go to graduate school. When I did get accepted to UC in a PhD program, I had this notion that it was an opportunity to go up on the hill and exchange great ideas, learn, and engage. While some of that happened, what really hit me was systemic racism and classism — I suppose there was gender in there too — and that shook me to my core. I didn’t anticipate this as an African-American woman raised working-class coming to a very elite institution. And while I had experienced personal racism and sexism, I hadn’t run up against the system. It became increasingly clear that students of color — myself included — were withering, and it wasn’t about us. When we brought this to the attention of the powers that were, we were met with, “We noticed this was a problem but think we aren’t selecting the right students.” At that point I woke up. I was looking at all these brilliant students of color…brilliant. The administration noticed the problem and their response was “the problem is you.” When I woke up to the systemic nature of oppression, it was not just personal, hateful stuff people can and will do. At that point I left the ivory tower with all but dissertation and started working on anti-racism, anti-oppression, and diversity work. I made my living doing that work for many years. Eventually I shifted from that limited cage, which felt like diversity was just too small. I shifted to the work of leadership — social transformation leadership specifically — and have been swimming in that pond ever since.

What are your favorite types of challenges?

There’s an interesting challenge of being human and loving and real and authentic in the context of fundraising. There’s a weird dance that generally has to happen or is expected to happen between funder and grantee…power stuff where I’m one down and they’re one up…all that mess that I just refuse to play. My building relationships with folks who will support the work of Rockwood is about building authentic relationships. I don’t want to care about the person’s power. I care about the person. I don’t want to — almost refuse to — negotiate that “you’re important because you work here or have this title.” Sometimes that’s a challenge because the game is so intense. To do the “oh I should be saying ‘thank you for taking a meeting with me’” when it benefits both of us that we know each other. How do we show up in a real way and step out of the prison of our roles? They (our roles) are functional and don’t tell us anything about what this human might be.

I enjoy that challenge, particularly as a Black woman since people have all sorts of notions about who I’m supposed to be, what I care about, what I’m supposed to say. When I show up as Akaya Windwood, an older Black woman, I show up as me and expect others to show up as them. That’s always interesting.

I sometimes find myself rehearsing conversations in my head before I have them when there is a power differential, which may not be such a good thing, but it helps me to show up. Does showing up as you take preparation?

I’m 62 and I’ve been preparing all my life for this. When I was younger I was careful with who I was talking to, thinking about what they needed to hear. The world is not set up for Black women’s authenticity, but I realized that I’m much happier — and the world is in better shape — when I am for real. I needed to get old enough for people to take me seriously and that’s one of the travesties of ageism. I’m watching what’s happening to young people who are coming out against gun violence. What do you mean we can’t take them seriously? That’s adultism/ageism. I finally realized that the world is not served by me playing small. If someone says my authenticity makes them uncomfortable, that’s fine — there are others to play with.

What is one book that was meaningful or influential in your development as a leader?

I read a lot of science fiction. As a genre, it allows for imagining what might be possible in the world. These days I’m not reading anything written by old white men anymore at all. Those voices have been overheard. I’ve heard enough. Unless the voice is a fresh one or a voice that we haven’t heard, then I’m just not reading it. Over the years…Octavia Butler…Ursula Le Guin…Alice Walker.

I’m wanting to read about ideas that connect us, that diminish the artificial barriers we call race, class, gender — all of that — reaching for something about our common humanity. We are living in a world where our common humanity is not exercised very often. I want to listen for a time when post-racial is actually true, and I do believe we can get there, and we ain’t there. This in-between time of hyper-alert race, class, gender oppression is useful — we can’t afford not to pay attention to it, but it’s also limiting us. We are far more than stories of oppression, both individually and collectively. That was one of the gifts of Black Panther. That’s how a woman moves when she’s not fettered by sexism all her life? That’s how Black people act without having the mantel of race on our shoulders for a lifetime? The movie was the counter conversation to Get Out. I want to know what it feels like to live in a time where it’s not even about Black people because it’s about people, and it’s not about women because it’s about people.

To go full circle on this, this is why I don’t make plans. If I make plans they are in relation to what’s available to me now instead of what I might dream. I don’t want my path to be limited; the world has so much more opportunity than what I currently know.

Work in the social sector can be very personal and linked to one’s values. Can you think of a time when your values were in tension during your career and how you reconciled that tension or not?

It goes back to trusting the path. If something was out of alignment with my values, I stopped doing it. I’ve been fortunate to either have my own business where I could choose who I worked with or not. I chose to come to Rockwood where who I am and what we do is just aligned. That partly has to do with the fact that I’ve been able to shape Rockwood over the last 12 years in alignment with my values. It’s partly because I haven’t worked for anyone else. I certainly work for my board, whom I love, and we trust each other. There’s a deep alignment between the values my board holds individually and collectively with what Rockwood believes in and what I believe in.

What’s your approach to self-care? Are there any rituals you use to survive and thrive?

I don’t actually love the term “self-care” because it makes it sound like I am caring about myself. Part of my responsibility as a community member is to care for my being, not the self as a separate thing other than connected to other people. “Self-care” sounds like I am going to take this elitist step away from the world because I can, which is different than understanding that my wellbeing is inextricably connected to your wellbeing. I want you to be well so we are well.

At Rockwood we call it personal ecology — being part of a broader ecosystem. It doesn’t serve the forest if the oceans are sick. Similarly, we can’t have a healthy community if we individually are sick. It’s my responsibility to tend to my self and wellbeing in service to our collective health and wellbeing. I can’t see it any other way. When I sit in my garden and put my hands in the dirt, I’m very aware that my hands are connecting with dirt that has been here forever, that my ancestors have worked, that holds the imprint of the roots that have decayed, and the animals that have lived and died. It’s a whole thing. I’m not just gardening for me. I’m also gardening for the neighborhood. It’s good for the bees to have blossoms to pollinate which is good for the trees which are good for the children. What you call self-care, I see as caring for the world.

I do garden and sit at my altar and often as a I can I take a walk around the lake. If you want to have a meeting with me, ask me to take a walk around the lake. That’s going to be a very different conversation than a strategic meeting in an office.

What advice would you offer other Black women trying to develop or amplify their voice and become self-advocates?

Trust your intuition. Trust your wisdom. Do not trust what you think! Don’t trust what you know. There’s a wisdom that we carry that is deep and it’s from our wild places — places where we are not tame. Trust our deepest wisdom that is clearly on purpose. Those messages are often at complete odds with what our social systems would tell us. The minute we have a doubt as to whether we are worthy or any of that, that is the voice of our internalized oppression and it is not true. Every single one of us is worthy. Every single one of us deserves grace and respect and to be loved. That is the only truth I know. So, when we forget — and our social system would ask us to forget! — it’s important to reach out to each other: Girl, I know you are worthy. You may have forgotten for a moment. Remind each other when we forget that simple truth.

I’m not sure how important amplifying voices is, but believing in ourselves and each other is more important to me…refusing to be hoodwinked by the lies of any system that would tell us anything other than the truth about our inherent worthiness.

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