Harold Phifer’s journey is far from ordinary. Raised in a world where hustling was a way of life and obstacles came early and often, Harold turned many hardships into stepping stones. From his modest beginnings to life-threatening experiences in warzones across Iraq and Afghanistan, Harold’s life could easily be described as a gripping novel—yet it is all real. Today, he is an accomplished author, international contractor, and speaker who draws inspiration from his raw life experiences to craft stories that inspire, entertain, and promote healing.
Southern Roots and Early Lessons
Growing up in the deep South wasn’t easy. Harold learned early how to work the streets, hustle his neighbors, and bus tables in bars that were perhaps not meant for him. These early experiences shaped a fierce independence and resilience that would later come to play a significant role in his life and writing. After graduating from Caldwell High School, he continued his education at Mississippi State University and Jackson State University—a remarkable accomplishment in his neighborhood at the time.
Despite academic success, Harold never truly felt settled. The traditional 9-to-5 lifestyle did not entirely satisfy a man destined to collect stories from around the world. But first, he began a stable career as an air traffic controller with the Federal Aviation Administration in Memphis, Tennessee. For 23 years, he guided airplanes with precision and calm, even as an internal storm of restlessness brewed.
A Life Reimagined Overseas
At the age of 45, Harold made a bold decision. He walked away from his secure FAA position and took a leap of faith into international contracting—a world filled with risk, danger, and the unknown. He spent several years in Iraq, working alongside soldiers and government officials during some of the region’s most volatile years.
In October 2011, due to the U.S. military drawdown, Harold was asked to leave Iraq. But his story didn’t end there. He resurfaced in Afghanistan, working as a contractor and, in his own words, a mercenary. For eight additional years, Harold faced the perils of conflict zones, witnessing trauma and heroism in equal measure. When the Taliban took over Afghanistan in August 2021, Harold once again had to flee for his life.
This time, he landed at Guantanamo Bay Naval Base. Under the protection of a secure environment, he returned to a familiar role as an air traffic controller. But something had shifted. Harold began pouring his experiences onto the page, channeling years of chaos into cathartic storytelling.
From Trauma to Triumph: Becoming an Author
Harold’s debut title, Surviving Chaos: How I Found Peace at A Beach Bar, is more than a memoir—it’s a personal exploration of the mind of a man who has faced numerous challenges and lived to write about them. Through the character Dylan, Harold reflects on his own past—a tapestry of trauma, absurdity, and ultimate resilience. The book has resonated with readers worldwide, offering not just entertainment but healing.
His follow-up, My Bully, My Aunt, & Her Final Gift, showcases Harold’s knack for blending personal storytelling with insightful cultural observations. The book follows his contentious relationship with a religious aunt who tried to derail his childhood ambitions, and how life came full circle when he was asked to deliver her eulogy. Through stories like “Two of A Kind,” “Letters to Santa,” and “Columbus Has Talent Too,” Harold shows how sometimes the biggest obstacles are the ones closest to home.
The Power of Voice and Representation
What sets Harold apart as a writer is his voice—raw, honest, humorous, and unflinching. He writes with a street-smart clarity and emotional depth that resonates across demographics. His stories are not sanitized for comfort; instead, they reflect the world as it truly is, especially for people growing up in marginalized communities.
Harold uses his platform to highlight issues many would rather ignore: familial toxicity, systemic racism, religious hypocrisy, and the silent scars left by war. Yet, he does it all with grace, often wrapping pain in humor and wisdom. It’s this balance that draws readers in and keeps them turning the page.
Writing Under Two Names
In addition to publishing under his real name, Harold also writes under the pen name Dean Conan. This dual identity allows him to explore a broader range of topics and styles, further showcasing his versatility as a storyteller. Whether it’s non-fiction memoirs or fiction inspired by true events, Harold ensures every piece carries his unmistakable signature of truth and transformation.
Readers R Leaders: Inspiring the Next Generation
Harold lives by the mantra: “Readers R Leaders.” He promotes literacy and storytelling as essential tools for personal growth and empowerment. He’s donated books to the Women’s Prison Book Project of Minnesota, the USO, and libraries and schools across the United States. His mission is simple but profound: to help others see themselves in stories and believe in the possibility of change.
His target audience is as diverse as his own background. From Christians navigating family tensions to memoir lovers, urban readers, and anyone healing from generational trauma, Harold’s work speaks to a wide range of individuals. Women, in particular, have gravitated toward his stories for their emotional authenticity and raw honesty.
Taking the Stage
In 2025, Harold will appear at several major book events, including The Great Midwest Book Fest (June 21), Book Lovers Con in Las Vegas (May 15–17 under Dean Conan), and The 5th Annual Philly Indie Books & Jazz Festival (June 7). These events give readers a chance to engage with the man behind the stories and understand the real-life moments that fuel his writing.
The Man Behind the Books
Outside of writing, Harold remains active in the international contracting field, currently back in the Middle East. Yet, no matter where he is, his heart remains with storytelling. He sees every person as a story waiting to be told, and every moment as an opportunity to learn, grow, and evolve.
His social media presence reflects his dynamic personality. On platforms like Instagram, X (formerly Twitter), Facebook, and LinkedIn, Harold shares everything from humorous takes on current events to behind-the-scenes insights into his writing process. His website, RiseAndRead.com, serves as a hub for his work, updates, and personal reflections.
Harold Phifer isn’t done yet. With more stories to tell and a growing fanbase eager to read them, the future looks promising. His writing stands as a testament to the power of perseverance, the importance of truth, and the healing that comes from putting pain to paper.
In a world that often hides its scars, Harold proudly shows his—not for pity, but to prove that survival is possible, that healing is real, and that every life, no matter how chaotic, is worthy of meaningful growth.
Published by Jeremy S.
