Hi, I’m Raymond Singletary.
An educational career coach, who is a 25+ year educator who served in roles like: HR supervisor, district supervisor, district specialist, high school principal, department chair, math teaching enthusiast, self developer, and podcaster with a proven track record of partnering with educators to create a sustainable, satisfying, and purposeful career.
Born in New York City, and raised in rural North Carolina, as a first generation educator, I’ve had the privilege of experiencing and learning from diverse communities. Despite the difference, I’ve learned that we all want the best opportunity for a happy and purposeful life.
How Did I Get Started?
To be honest, education was not my first choice, I wanted to be a computer programmer and create video games. But, my family could not afford to pay my schooling, so I was fortunate enough to be advised by my teacher (Ms. Faulk) to apply for a teaching scholarship (Teaching Fellows of NC), which I was able to successfully obtain. The rest is a rollercoaster of developments.
I struggled in college and for the first time, I didn’t know how to respond. I avoided the work, but I was lucky enough to have one professor (Dr. Lee), who provided me with a statement that changed my life. He told me “It doesn’t matter where you are now, its how you choose to finish.” This is a mantra that I still carry with me today.
From that point on, I wanted to be that educator for someone else. This person that no matter what is happening in someone’s life, I would be there to support his/her learning.
This drove me to seek educational leadership opportunities, and after I fulfilled my 4 year obligation to the scholarship, teaching high school math, I decided to start on this path to being a principal.
Educational Leadership (My Bumpy Road)
was a middle school Dean who believed I was ready for the next step. I had observed teachers, led special education processes, built master schedules, and supported instructional growth. After moving my family to a new area, I felt confident I was on the path to becoming an Assistant Principal. Then the district defunded the Dean program, and almost overnight, I lost my job.
The pressure was immediate and real. I either had to land an Assistant Principal role or return to the classroom—over an hour away—with serious financial consequences. I applied everywhere and interviewed often, but the rejections kept coming. The feedback was vague and frustrating: I wasn’t ready, I lacked experience, or I didn’t “tell my story.”
The lowest moment came when I interviewed for an Assistant Principal position at my own school and didn’t get the job. I was devastated, angry, and confused, but quitting wasn’t an option. That’s when I realized the real problem wasn’t my experience—it was my ability to clearly communicate my value in resumes and interviews. Once I learned how to communicate my leadership impact strategically, everything changed.
Five years later, I became a high school Principal, and new opportunities opened faster than I ever imagined. That journey is why I built Educator Career Coach—to help educators avoid years of confusion and rejection. If you’re ready to move to the next level but aren’t getting clear feedback or results, you don’t have to figure it out alone. Join the Educator Career Coach community and learn how to confidently communicate your value and land the role you deserve.
What was missing?
What I didn’t realize is that I wasn’t aware of my own strengths! Even bigger than this, I didn’t know what I stood for and I lacked the ability to socially connect because of it. So, I learned that I needed to figure out ME and develop my social skills in order to get to the level I desired.
Lucky for me I have a loving and supportive wife. She continues to push me and believe in me! So, I decided I could not give up!! I made too may promises to her, myself, and community I wanted to serve everyday.
So, I started searching for some answers. I looked for anything on personal growth, high performance, mindset, communication, relationships, goal setting, and more. I found articles, videos, podcasts, workshops, and read anything I thought might support my journey towards getting better. After, 5 years, I finally obtained the role of School Principal at Sun Valley High School in NC.
Even though, I chose to go in a different direction in educational leadership, I am proof, that it’s not just about hard work, it’s really about figuring out the “right” work for you and doing that work consistently. I believe that anyone can do the same, however I don’t want you to do it alone because it is really hard (continues to be hard). My desire is to share all I have learned and be your personal coach as you develop your personal skill to become that school leader you have always desired.
I want to thank my loving wife, Michele, for being my rock then, now, and forever! I love you!