Today we’d like to introduce you to Penny Dickerson.
Hi Penny, so excited to have you with us today. What can you tell us about your story?
Jacksonville became my home in 1977 following my father’s military retirement. My mother’s water broke in El Paso, Texas and I was born on Ft. Bliss Army Base and the youngest of three girls. While my origins align with the Border of New Mexico, every two years it seemed we were domiciled in a new state including Georgia, Washington state, a Texas repeat and my father’s last duty base: Ft. Ritchie, Maryland. Our family returned to Jacksonville because it was my mother’s home and all three of her daughter’s graduated from Nathan B. Forrest High School (renamed Westside High School amid racial strife). From navigating snow through 1st and second grade in Germany to hopping on subways in Philadelphia, being transient and in motion has always been embraced as my new normal.
In 1988, I earned my Bachelor of Arts degree in Journalism from Temple University followed by a 15-year gap and pursuing a Master of Fine Arts degree in Creative Writing from Lesley University in Cambridge, Mass. The least of my life’s surprises is that my career as a journalist would come full circle following stints in retail management,
corporate fundraising for United Negro College Fund to enduring days as a classroom teacher and falling in love with young adults as an adjunct English professor.
My love for reading began in my formative years. James Baldwin and Mark Twain were early influences as much as Beverly Clearly. Military bases had skating rinks and movie theaters but the library was free and my mother was not an advocate of boredom. “Read a book!” she would bellow. And that’s what I did. My love for the written word was insatiable and I learned to both read and write poetry and prose that made language dance. Journalism was more of a reinvention of self following a 2006 cancer diagnosis. The Zora Neale Hurston festivals opened doors for one festival story at a time (pro bono) to greater heights of being awarded seven Journalism fellowships and high profile interviews with celebrities, ONYX Magazine cover stories, and a diverse body of work that now defines my resilience and perseverance. My nickname is “Pennyfly” because I championed cancer in the tradition of Muhammad Ali: “Float like a ‘Pennyfly’ sting like a bee.” It later became a poem.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Without pause, I offer cancer as my life’s greatest challenge. As mentioned, in 2006 I was diagnosed with Renal Cell Carcinoma (kidney). Two decades later I am still fighting like a bee with fly-sting. I have had a recurrence in 2017, 2020, 2023, and yes: in February 2026, I had tumors frozen via cryoablation at UF Health Shands. I have also received treatment at M.D. Anderson (Houston) and Mayo Clinic (Jacksonville) It has been more than a notion to conquer cancer only for it to follow me like Mary’s Little Lamb. At each pivotal employment coup, cancer recurred. In 2020, I was editor of The Miani Times. Six months into the gig: I had a cancer recurrence. In 2023, I was a reporter with The Jacksonville Business Journal. Six months into the gig: another cancer recurrence. The urology team at Shands, a teaching hospital, is pursuing genetic tests to determine why my kidneys grow malignant tumors. The challenge has been stability, maintaining a positive attitude and relying on my Christian faith. My prayer life and seeking God deeper has kept me afloat and mentally sane most days. My village is also strong and includes my family, daughter Kelsey (35) and grandchildren Journey (14), Isaiah (10) and Mya (3). My son-in-law of ten years is Donte Boyer. He holds their Tallahassee home. My first cancer treatment was a partial left nephrectomy which left a left-handed me with three resected ribs and severed nerves. My range of motion was so affected that I could still write in a classroom on a dry erase board, but I definitely couldn’t withstand pain eight-hours per day. So tenacity kicked in and teaching took a backseat to journalism’s forward drive. The latter is remarkable given the struggle and sudden stops, but oddly, I take it all in stride and remind myself that God has a purpose for my life, and I am applying for a Marijuana Card for pain. Another salve to soothe my soul is an occasional Chick ‘fil A ice cream cone. I have learned to never crave that delectible custard on a Sunday!
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
As a creative and content creator, I work as an Independent Journalist who has contributed to an array of digital and print magazines and newspapers. My journalistic approach is known for finding unique angles to stories and seeking to make the human condition palpable. I gravitate toward profiles and cover stories for ethnic media; however, my portfolio is diverse: I can pen an image-driven feature for the Orlando Sentinel Magazine or indulge in research for more indepth coverage of “Kongo Across the Water” for Ebony.com. I’ve been blessed to write numerous cover stories for ONYX Magazine. The overarching theme for my writing life has been transparency and storytelling that has range and is raw. I am set apart from peer writers in that my work ethic dictates that no one in a room will work harder than me. I recall one of the nine years I covered the Disney Dreamers Academy with Steve Harvey and ESSENCE Magazine. I went to Orlando to cover Florida’s student representation and left the Magic Kingdom with four additional stories after meeting celebrities and other persons of intrigue. I am most proud of using a trifecta of digital platforms for funding one of my life’s dreams to travel abroad to the Motherland. In 2019, I was one of two volunteer writers who traveled aboard the Africa Mercy in Dakar, Senegal. It was a costly endeavor, but not beyond the realm of what Pennyfly was built to accomplish. Utilizing gofundme.com, Facebook and pennydickersonwrites.com, I raised 16K in 30 days with just 44 donors. I am strategic and exhibit extraordinary resolve while my ability to stay focused is one of my better attributes.
Do you have any memories from childhood that you can share with us?
Growing up a “military brat” seemed to be an ideal life if you were not the soldier commissioned to salute. My childhood was unique and the most fond memory would be seeing snow on Christmas day versus wearing flip-flops in Florida to celebrate my Savior’s birth. I was a long, lanky, and awkward kid with huge brown eyes that would later become an asset when I was crowned the first Black woman to win the title Miss Florida Junior College (now FSCJ). College was not subjective in our household. Both sisters entered the armed forces and it was incumbent upon me to figure out how I would finance academic pedigree. Pageantry proved feasible and triumphant, and I won a string of teen pageants including Miss Delta Teen sponsored by Delta Sigma Theta Sorority, Inc. It was my first win, and I would be remiss if I did not mention that I am a proud member of the first Sorority founded for Black collegiate women in 1908: Alpha Kappa Alpha Sorority, Incorporated. It feels a bit arrogant to throw in that I am also a former Miss Black Florida and there are other titles of note, but scholarships were available and playing “Flight of the Bumblebe” on a mahogany wood xylophone brought home many tiaras and crowns. The full-circle childhood memory, the take-away, is that being raised in unique environments was instrumental in my becoming an adult who adapts well to new situations and a girly-girl who gives God all the glory.
Contact Info:
- Website: https://Pennydickersonwrites.com
- Instagram: @pennyflywrites
- Facebook: https://www.facebook.com/pennydickerson
- LinkedIn: https://www.linkedin.com/in/pennydickerson/
- Other: Pennydickersonwrites@gmail.com
