We had the good fortune of connecting with Graylyn Swilley-Woods and we’ve shared our conversation below.

Hi Graylyn, what role has risk played in your life or career?
Risk-taking is part of my DNA. Not only was risk-taking critical in my career choices it kept life exciting. I believe calculated risks are the best types of risk. If computed correctly risks are bound to take you to the next level. I recall starting my first business venture. I had no plan, just experience with my product. I left a secure job and learned how to get better at what I wanted to achieve. That experience placed me in touch with new potential and talents. All along the way, I wanted to make good decisions that would lead me to a quality life. Now, I use those insights I gained from the many risks I took to look ahead with vision and discernment.  Calculated risks I take more of today are based on my wisdom and maturity. It is essential to know yourself and your vulnerabilities. In other words, placing yourself on the line… that is being uncertain is a sure way to hone new talents. As a result of risking taking, I acquired an entirely new set of skills that placed me in unexpected positions which brought new opportunities. Thus, I learned to trust myself and to unlock doors that I hadn’t even considered. Risk-taking enabled my creativity, independence, courage, and entrepreneurial talent. Taking a risk is important to me and as previously stated is built into my DNA. It is my product and brand that differentiate my work, career goals, and aspirations. Have I had miscalculated risks? Yes indeed. They provided me with valuable business instructions as an entrepreneur and executive. Thus, I am always looking ahead willing to take risks to shape new and innovative business strategies and to enhance my personal growth.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.

My career has had many pathways filled with energy and compassion. Before starting my career, I thought it would be a sinch. I heard from family and friends all of my life “Go to college… go to work… get a good job… have a good life… you will be happy” … Instead, it was a long, often uncertain, and constantly evolving journey. I did obtain good jobs, earn competitive salaries, and learned that happiness is not found in a bottle. I would have never guessed that the wealth of experience I gained over the years and the maturation process of getting there would be as rewarding and long-term as it has been. And I never thought that my passion for my work would still be burning and the feeling just as exciting. My career path evolved from being a student leader to mid-management, onward to Executive Director roles of several nonprofit organizations in cities across the country, culminating to a VP on corporate levels, to a social entrepreneur, scholar-activist, and thought leader today.

What sets my career pathway and me apart from others? It is my willpower, adventurous personality, and decisiveness to advance and move ahead. Before I launched my career, I had limited resources and a lot of determination. I was unaware of the absolute need for money and resources and how they are equivalent to success. I only knew I had to complete my education and learn to stand up to the circumstances that were waiting ahead. I recalled arriving at The Ohio State University only to be informed as I waited outside the Bursar’s office that my scholarship went to another student. I was unaware that my scholarship would be delayed for an entire year if they had not heard from me on a specific date. I was devastated and lost. Having arrived in the dead of winter, I had to decide: stay and figure it out or return home and wait another year. I took a risk and remained in Ohio with friends I made from Pittsburgh during my undergraduate years. That experience brought me face to face with the meaning of “perseverance and tenacity”; I had to draw from a deep source of faith that remains an active part of my career journey today. The scholarship experience taught me not to give up in the face of adversity and to stick with my vision of self. I never guessed that the experience and the growth process would be as rewarding and long-term as it has been, and I never thought that this passion would last so long; I guess I got lucky!

My journey to the current professional place I am in today has had multiple pathways. My professional interest has always been motivated by “my personal mission” to serve others, especially African American communities and those who are in need regardless of background. This interest grew from childhood as I watched the civil rights movement unfold, similar to witnessing the riots after the murder of George Floyd.

My professional career began as a student leader at the University of Pittsburgh, where I was elected the President/Chairperson of the Black Student Government. Before my signature had thoroughly dried on the document, I signed on as the incoming student leader. A series of unexpected events required me to organize a student body to reinforce the need to establish the Department of Black Studies. At the time, there were limited course options on African American history, science, and politics. As a student leader, I wrote articles, delivered speeches, and, most importantly, acquired a prospective passion for racial equity, and an urgency to address social injustice and the power imbalances pervasive in our social and economic systems. My years as a student leader prepared me for the professional careers I have today. In each leadership position I have held, there were platforms to question and address sensitive issues that affect society. I identified problems that hindered progress while simultaneously seeking to create knowledge and understanding to improve community functionality.

As a scholar-activist and public servant, reaching success is no “cakewalk”. It is a journey! It requires refueling the heart daily while addressing the needs of others. I want others to know I took risks to serve others while keeping close to my passion; today, my risk-taking is more premeditated. At the end of it all, the career opportunities  I experienced were about learning yourself, sticking with your goals, and doing it “my way”. I found the “silver lining”. I want others to know voice matters, and risk-taking leads to new challenges. Standing up for what you believe in can lead to a rewarding career. Finally, networking has been foundational and fundamental to my career success. Without networking, meeting people, and following up with them, my career pathway would not look anything like it does today. People, and the resources they bring, are critical to helping others reach their goals. No man is an island; networking or what I call “peopling” is substantial to career building and is key to the overall human experience.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
There are many fun and interesting places to share with friends who visit the Miami area. My most favorites are Historic Overtown, Little Haiti, Little Havana, and Miami beaches, all are my favorites…..LOL. Of course, these places have their unique flavors and I will share.

Let’s start with Historic Overtown. A community under change. In some ways, the change is good, and in other ways not so. Rent is outpacing the locals. The nightlife is picking up. I really enjoy the Lyric Theatre events such as Lyric Live and the Comedy Jam. The Red Rooster Restaurant, the latest “foodie” place in Historic Overtown, offers a superb dining experience filled with locals and tourist energy, a must-visit. The Dunn Josephine Boutique Hotel is another new venue in Historic Overtown. It is a place of culture and history especially for those who want to get in touch with African American “roots”, visiting this place will take you there. Pillows on the bed and pictures on the wall from back in the day of historical figures who performed in Overtown will make you smile. Imagine running into Aretha Franklin, Mouhamed Ali or Langston Hughes on 3rd Ave in Historic Overtown. Visitors and residents alike are introduced to the history and culture of this community. The Urban Open Space is another entertainment venue I enjoy, the Wards Rooming House Art Gallery, The Little Greenhouse Restaurant is yummy – the best soul food in town, and the overall ambiance of the community is being elevated with the redevelopment being experienced.

Little Haiti, another favorite place is vibrant and also experiencing changes similar to Historic Overtown. I recommend Chef Creole for eating out and the Haitian Cultural Complex for entertainment. There is a TAPTAP bus that is available for a tour of the community. Little Havana, Ball and Chain restaurant and entertainment spot, the streetscape with its live music on the sidewalks are all exciting. These are places I always send visitors and my friends to check out.

Who else deserves some credit and recognition?
My Shoutout is to Dr. Dorothy Fields an important person to me, to the community of Historic Overtown, and to the city of Miami. She is the founder of the Black Archives and Lyric Theater, mother, grandmother, friend, and more. She is the “Cat’s Meow”, someone special. I want to shout out and thank Dr. Fields for living at this time. To keep us “woke” and caring about the people who cared that we got this far. Thank you, Dr., for helping me cross the line…only to get to another one and another one.

Website: www.overtowncyc.org

Instagram: https://www.instagram.com/overtowncyc/

Linkedin: https://www.linkedin.com/in/graylynn-swilley-woods

Twitter: https://www.twitter.com/overtowncyc/

Facebook: https://www.facebook.com/overtowncyc/

Youtube: https://www.youtube.com/channel/UCHnspXD2yruLvdWOSo3zldw

Image Credits
Lakiesha Nicole, LLC.

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