We caught up with the brilliant and insightful Darrell Holloman a few weeks ago and have shared our conversation below.

Darrell, thanks for taking the time to share your stories with us today How did you come up with the idea for your business?

One night while serving in the Peace Corps in Cape Verde (West Africa), the volunteers (including myself) got into a debate about what was the most important thing the American education system was missing. My argument was career exploration and mentorship. Before then, I didn’t realize I was so passionate about this. That night I couldn’t go to sleep and started writing down all of the ideas I had to fill this gap in our education system.

About a year or so later, I became a Social Studies teacher at my high school alma mater, Bishop McNamara. This experience only further confirmed my argument. Students with high grades to low often knew that they were supposed to go to college, but didn’t know what to do after they got there. Many students had never explored careers and often wanted to have careers that they were exposed to by TV or relatives, but many had not truly explored these careers.

After 7 years of teaching at my alma mater, I moved to Yap, Micronesia. This opportunity finally gave me the time to create a business plan for my career mentorship program. When trying to come up with a name, I realized the theme I used for my class was perfect, “We are all educators!” I then realized that the acronym was W.A.A.E. (pronounced way). I then decided to make it a play on words and officially named it The We Are All Educators, Org. (a.k.a. The WAAE).

When I returned to the U.S., I continued teaching at Eastern Senior High School in D.C., while simultaneously working with the George Washington University School of Law clerkship to register my nonprofit. Once The WAAE, Org. was established, I told my coworkers, and they were immediately ready to give me 75 young men to work with. When I talked to the students about it, the young women made it clear that they did not wan to be left out of the program. Since the beginning, there has been no problem with demand for the program from students, parents or the community. The only issues we’ve had is financially being able to support the program, so that we can provide help to as many students who want to be a part of The WAAE.

The students are not only asking for career exploration, but also guidance on how to make the best decisions that will lead them to the life they dream of having. What makes The WAAE unique is that we not only allow the students to tell us what they want in their programming from us, but we help them until they reach their desired career. This means that we do not stop at high school, college or vocational school, but we vow to assist until they no longer want or need our support.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

My name is Darrell Holloman, Founder and CEO of The We Are All Educators, Org. (The WAAE pronounced “the way”). Though I’ve known I wanted to be a teacher since I was 5 years old, I started working at 14 years old and have held nearly 40 jobs. My main career has been teaching, which I’ve done for over 15 years, but I have also been a DJ for nearly as long. I truly believe that I have had so many jobs because it has prepared me to help others in various careers.

The WAAE is a career mentorship and professional development nonprofit that helps people figure out what they want to do, create a plan and then execute that plan. We provide resources for whatever our students need to help them reach their goal of obtaining their desired career. The WAAE is unique because we don’t “cut the cord”, meaning we help students from the time they join our program until they reach their desired career or no longer want or need help from The WAAE. We understand that most of our students join the program in high school, and that there is so much more that they need after that to help foster their success and to reach their desired career. Some of these resources include: assistance with college or vocational school applications, resumes, interview workshops, financial literacy workshops, connecting students with professionals in their desired careers, community service, etc.

We are most proud of our students. As an organization, we are most proud of how much we’ve accomplished with minimal funding. We have employed over 150 students, assisted more than 700 students with career exploration, we have a 100% high school graduation rate and more than 95% of our students pursue a career explored during our program. We have also completed nearly 1,000 community service hours. We know that we can do so much more with the proper funding.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I am ambitious. If I believe that I can do something, I dive head first into it. I’m also a visionary, so if my vision does not play out the way I think it should, I get frustrated and discouraged. I often see this as a failure. The visionary in me saw The WAAE, Org. being much bigger than it is right now. There are goals I had for The WAAE, that I thought were going to be accomplished in year one that we haven’t been able to accomplish in year seven.

The visionary in me still fights with the fact that “my vision” has bot been fulfilled. The wiser Founder/CEO me understands that every business, nonprofit, person, etc. does not work on the same timeline. The successes that I were going to be easier to obtain will take some time. I cannot tell our students that they are the standard and that they should not compare themselves to others, and not do the same for myself. I also recognize that it’s not all about my vision of what success is. Our students are more and more engaged every year, and sing the praises of how The WAAE has helped them. Though my personal desire is often to do more. I need to recognize when we’ve done the best that we can do, and understand that effort has created its own success.

Though I will not fully let go of what my vision is or definition or success, I must recognize the wins along the way, or I’ll lose sight of what we are doing this for in the first place. The goal is to help others. The nonprofit is focused on students’ desired career, but we may help students in ways we didn’t expect that are unrelated to careers, and that’s okay too.

Any advice for managing a team?

I will reiterate that we are very small, which may attribute to us having pretty successful management and high morale. As the CEO and overall manager of most things, I constantly ask myself, “How would I like to be treated in this situation?” When I do that and act accordingly it usually works. I am in no way perfect when it comes to management, but I have found that asking that question helps. I also try to keep the lines of communication open with those I am managing. This can also be tricky, as there is a power dynamic often at play and people may not always be truthful. Be as genuine as you can, while maintaining a clear understanding that this is your business without being rude or overbearing.

Contact Info:

• Website: www.wearealleducators.org
• Instagram: @wearealleducators
• Facebook: The We Are All Educators, Org.
• Linkedin: Darrell Holloman II
• Twitter: @TheWAAE
• Youtube: The WAAE

Image Credits
D2D Focus – for the headshot Taylor Brown 31, LLC