Introduction and Shared Connections
Taryell Simmons: Welcome, ladies and gentlemen, to another episode of Rise Urban Nation. It is your host, Taryell Simmons, and I have a special guest in the building today. We share a mutual acquaintance we both dearly admire: the amazing Roxanne. When Roxanne was with RISE San Diego, she was actually my coaching circle coach. How did you first meet Roxanne?
Rachel Wyley: In my past life as a nonprofit executive director, I was looking for someone to facilitate a racial equity conversation for my board of advisors. I love those conversations, but I knew as the executive director that I needed to be a participant in that room rather than leading it. I asked my team to research someone who could hold a real and honest dialogue. Roxanne was one of the names they brought, and as soon as you learn anything about Roxanne, you know you need to have her in the building. She facilitated that training for my board members, and to this day they still talk about how transformative it was.
Taryell Simmons: Roxanne is definitely a force of nature. If you are not ready to do some serious soul searching, Roxanne is not the one for you. For the folks listening, you have a lovely flower behind you and a board on the wall. What does that board say?
Rachel Wyley: It belongs to a family member, and it says, "Chance favors the prepared." To me, it means our blessings can find us if we do our work. Whatever we are called to do in the world, that is our unique assignment. The blessings and favor we need to walk that path can find us if we do our part. We have to listen intently to understand our specific role. I have an ongoing battle with God where He tells me, "Can you stop trying to do my job? Do yours. I got the other part." All things will find you, but do your job, be ready, and let Him take care of the rest.
Taryell Simmons: My auntie used to say, "You want to make God laugh? Tell Him your plans." The reason I started this podcast was because so many people have not found their path or remain stubborn about doing the preparation required. When I spoke at high schools, students would see a Black man leading organizations in HR and DEI and think, "You must be the only one." Then working with adults, I realized adults have limiting beliefs too about who we are and finding our story. Let us dive into your journey of getting out of your own way.
From East Oakland Educator to Executive Director
Taryell Simmons: You were an executive director twice, even though you never intended to be. How did that journey start?
Rachel Wyley: I did not choose it, I did not want to be there, and I said that out loud many times. When you tell God what you are going to do, He says, "You do not tell me what you are going to do; I tell you." I started my career as a teaching fellow with an educational nonprofit in East Oakland. I loved working with middle school students and learning from them every day. They have beautiful wisdom because they are actively questioning themselves and the world. My original vision was simply to be a teacher or a principal and give back to community that way.
Rachel Wyley: From teaching, I became an administrator coaching teachers, and then moved into program management at a health equity organization. Then my manager told me, "I know you are comfortable in this program director seat. But it is time to elevate. It is time for you to become an executive director." Two weeks later, an organization reached out to recruit me for an executive director role. I served in that seat for a couple of years, took on a fundraising leadership role at another organization, and ended my nonprofit career in a second executive director position. I was moved from place to place, and today it could not be clearer why I sat in every single one of those seats.
Taryell Simmons: Those people who pushed you along the way—would you call them mentors, or angels who saw something in you that you did not yet see in yourself?
Rachel Wyley: Both and more. Some were mentors who became trusted friends, but truly they were appointed angels. They told me, "You have work to do in this world. You cannot stay here; it is time to keep moving." I was blessed with people like that from my earliest jobs all the way through executive leadership.
Early Work, Style, and the Creative Foundation
Taryell Simmons: You mentioned working in Parks and Recreation early on. How did you get that job?
Rachel Wyley: Technically, my very first job at fifteen and a half was on the fashion board at Nordstrom, dressing mannequins and setting up display windows. But my first regular, year-round job was with Parks and Recreation when I was sixteen. I got that role because I had volunteered with the city since I was thirteen years old. When it came time to apply, I had years of dedicated volunteer experience, so they hired me as a recreation leader.
Taryell Simmons: You definitely brought that sense of style into the building today—the leather jacket, statement earrings from Barcelona, and that undeniable presence. You can tell immediately that you carry an artist spirit.
Rachel Wyley: You never know where things will end up, so you have to bring your best! But that artistic identity is foundational. Throughout my entire nonprofit leadership trajectory, I was simultaneously walking my journey as an artist—as a vocalist, poet, songwriter, and essayist. You do not have to choose between your professional career and your artistry. You can and should walk both paths. Your creative self informs every leadership decision you make.
Founding Culture Kinesis and Cultural Reimagination
Taryell Simmons: How did all of those experiences shape what you are building today at Culture Kinesis?
Rachel Wyley: Every single step prepared me for this work. Today, I am the founder of Culture Kinesis. Our focus is creating containers where individuals and organizations can engage in deep cultural reimagination, specifically around racial equity. Culture Kinesis does the work organizations need to do before they hire a DEI consultant or convene a DEI committee. It is about naming what currently exists, identifying what we need to unlearn and learn, building intentional community, and dreaming together rather than simply patching things onto broken systems.
Taryell Simmons: In so many institutional spaces, people cling to existing foundations even when they are harmful, saying, "We have always done it this way." How do you help people break through that?
Rachel Wyley: In order to upend the status quo and unseat centuries of oppression, we have to be extraordinarily creative. But capitalism does not teach us creativity. Many of us have forgotten how to dream because our creative self has been separated from our daily lives. That is why art is essential. We cannot bring the exact same tools and expect a radically different outcome. As an artist, I guide people to awaken their creative imagination so they can envision a future far better than anything they have previously witnessed.
Rachel Wyley: In practice, that work is a process of co-creation. I do not arrive with pre-packaged answers. Instead, I bring the questions that help people break open so others can see their deeper layers. Just like singing on stage, I know when an audience is merely nodding along versus when they are emotionally connected through shared vulnerability. In my coaching, I bring music into the space and lead storytelling exercises like "a room full of strangers." When colleagues look beyond formal credentials and connect with each other's full humanity, the work transforms entirely.
Navigating Power, Humility, and Institutional Limits
Taryell Simmons: If you were giving advice to someone navigating their career path in leadership or entrepreneurship, what critical steps would you highlight?
Rachel Wyley: First, start in a role that is as close to community as humanly possible. Loving and understanding community will anchor your entire career and shape every choice you make. Second, maintain your parallel creative path. Third, establish a clear vision for how you want to shift the narrative. But here is the hard pill to swallow: an executive director seat is a seat of power, but if the decision-makers around you have no interest in evolving, your individual power will not be enough to change the system. When you realize that existing institutions cannot hold your vision, you have to ask where your power belongs. For me, that meant stepping outside the nonprofit sector to build my own lane and apply pressure from the outside.
Taryell Simmons: That speaks directly to what I explored during my Rockwood Building Power fellowship last year. It forced me to examine how we hold power, yield power, and often give away power to institutions that do not serve us. It also challenged me to ask how I can best support Black women leaders, get out of their way, and lead with genuine humility.
Rachel Wyley: Humility is essential. Early in my career, one of my mentors told me, "You must always be both a teacher and a learner. If you stop learning, there is no hope for your leadership." Your team, your peers, and the community all have wisdom to teach you. If you are too arrogant to learn from others, you will never reach the true pinnacle of your leadership.
Black Women, Legacy, and Building Our Own Spaces
Taryell Simmons: What is one enduring lesson that life has taught you?
Rachel Wyley: Everything is relevant. I spent years feeling frustrated that I was placed in executive director roles I had not asked for. But looking back, it could not be clearer why I sat in those seats. The triumphs, the heartbreaks, and the relationships all taught me lessons that sustain me today. Often the experiences that feel most irrelevant turn out to be the most critical preparation for your calling.
Taryell Simmons: Black women are earning degrees and launching businesses at unprecedented rates, often without venture capital or traditional funding. What is driving this powerful movement?
Rachel Wyley: Black women are inherently divine, creative, and community-oriented. We reach a point where we realize we must fulfill the legacy we have been entrusted with. That is the very first conversation I have with every client: what legacy are you trying to leave in this world? When you get clear on your legacy, you recognize that traditional institutions cannot hold or nourish it. James Baldwin wrote, "The space that I will occupy will not exist until I make it." For years, I searched for an institutional home for my vision. When I realized it did not exist, I accepted that heartbreak and got busy building my own lane so that others could do their work as well.
Culture Kinesis and the Dandelion Movement
Taryell Simmons: How did you come up with the name Culture Kinesis, and what does it represent?
Rachel Wyley: When I was wrestling with naming the business, a friend helped me realize that what I was describing was kinetic energy. Real change only happens when things move. People have to move from power hoarding to power sharing, and from avoiding power to assuming power. You cannot simply shift your mindset; power, resources, and positions must move as well. At the root of any real shift, culture has to move.
Rachel Wyley: The visual metaphor I carry is a dandelion with white seeds. It only takes a gentle breeze to dislodge the seeds, and each one embarks on its own unique trajectory. When a seed lands, it takes the wisdom of its journey, plants itself, and grows something new. We cannot expect everyone to take the exact same path or arrive at the identical destination. Dandelions are often labeled as weeds, but they are incredibly resilient. We have a responsibility to spread out and plant a counterculture of positive transformation wherever we land.
Taryell Simmons: What upcoming projects are you working on, and where can people connect with you?
Rachel Wyley: You can learn more at culturekinesis dot com and follow on Instagram at Culture Kinesis. In 2022, I am hosting Call-and-Response with Culture Kinesis, a free monthly drop-in virtual space for Black women and women of color to shed the residue of oppressive systems and step into their power. In July 2022, I am launching a cohort for emerging Black executive directors, creating a supportive community where leaders do not have to navigate isolation and can thrive in their full, authentic Black selves.
Taryell Simmons: Thank you for creating that space and for sharing your wisdom with Rise Urban Nation. Everyone listening, please make sure to follow Rachel Wyley and support Culture Kinesis.
Rachel Wyley: Thank you, Taryell, for holding this space and for the beautiful dialogue. Infinite gratitude to community and everyone listening.
