Q&A with Damien Howard Chief Servant Leader of “Clever Characters”

For 13 years, Damien Howard taught Special Education at inner-city urban schools that served mainly low-income minority populations. But after seeing firsthand the disparities between urban and suburban education, combined with the dissatisfaction and lack of innovation within his peers, Howard had an awakening.

“As educators, we have the ability to be servants…. We have the opportunity to change lives… When I looked at my colleagues, I didn’t see fulfillment. These people were responsible for educating our youth. But then we ask “Why are our students underachieving?” said Howard. Howard soon realized that his skills and passion for education expanded beyond the classroom.

In July of 2017 Howard launched his business “Clever Characters”, to nature the growth off entrepreneurial and servant-minded leaders, who grow leaders and transform their communities.

As the founder of Clever Characters, he would lead a team of mentors and educators that served over 20 schools across Chicago, utilizing online tools to spread the movement to other communities.

Howard says his title “Chief Servant Leader” is intentional – he does not want to be CEO or the boss, but rather a chief, servant, a leader. “So many people articulate grandiose aspirations for themselves and visions that are magnificent. I don’t want to be any of those people who’s just about self service.”

N’DIGO sat down with Damien and talked about his family, Urban Education Reform, who inspires him and his business “Clever Characters”…

N’DIGO: Tell us about yourself?

Damien Howard: Hi there! I have an amazing wife Sharial of almost 15 years and we’re blessed to have a brilliant 9-year- old daughter name Gabrielle. Shari is a top realtor for @Properties and was featured in N’DIGO earlier this year.

I am very passionate about Urban Education Reform. I believe that the current structures in place are failing our kids who already live in the worst conditions. I obsess about ways to use Social & Emotional Learning as a lever for equity, diversity, and inclusion in our school systems. I want our communities to have further empowerment to raise our voices for equitable standards and opportunity – especially for people with minimal financial needs.

You taught special education in the Chicago Public School system for 13 years. What were the highs and lows of your tenure?

Highs – Being able to reach those deemed unreachable
Lows – Consistently seeing boys of color over-represented in the field and often “pushed through” the system.

What made you launch your business Clever Characters? Why the name Clever Characters?

I initially started my business with 4 high school teens from Crane High School. I started the company because I wanted to expose them to entreprenurialism. I thought they could learn so much from me during a summer launching a business with me. After the summer, they went on to their senior year or college, and I was left with a business. I then had to reach inside and imagine how to make this business work for me and allow me to explore my passions. At that, the mission of the vision changed. Initially, the kids and I went to schools and daycares as “characters” and would share helpful messages with kids – hence, “Clever Characters.”


What impact have you made on your students and community?

Over the last 3 years of my work, we have seen consistent improvements in classrooms we’ve worked with. We’ve seen improved grades, better behaviors, and even improved standardized test scores. The organization, CASEL (The Collaborative For Academic & Social Emotional Learning) has done several studies expressing the impact of SEL in schools. I have consistently seen the impact of SEL in the classrooms we’ve partnered with.

Now, we are focusing more on training the adults who work with kids. As we train parents and survey them concerning the impact made, the surveys consistently express that parents are more equipped to cultivate the character of the kids after going through training with us. Parents admit that our training also helps them to regulate their emotions to lead better lives themselves.

What special education strategies and techniques have you applied to help those you mentor?

Special Educators are often stated to be “special people.” I am very patient and I think part of that comes from my persistence as a SPED teacher. My profession taught me to love those often deemed as unlovable. My love empowered me as an advocate and freedom fighter for my students. These are things I advocate for through mentorship too.

What is Social Emotional Learning (SEL)?

I simply speak of it as the following…
Strategies (Learning) that help me to relate to others well (Social) and strategies that help me to understand and manage my emotions (Emotional).
How do you equally help the student and the educator?
Both can get SEL training and focus on character development to accelerate the creation of a winning school culture. We’ve offered training for adults (teachers and parents) and direct SEL Mentoring services for students.

What key components are needed to help students with educational, social and economic challenges?

I think SEL is a key factor that will impact change. Amidst many other factors, SEL has the ability to help students better advocate for favorable conditions for themselves. Empowered kids of all ages and informed parents will be the most powerful agents for education change that this nation has ever experienced.

How do you ensure that students and teachers received the right type of support?

In part, my work is less about telling them what and inviting them to explore what with me. I often say that I strive to be a guide along side versus a sage on the stage. We create safe spaces for parents to explore different topics together. This type of approach allows for parents to speak their truth and get input based on their needs and in the unique manner that speaks best to them. This approach thrives because we tap into the power of collective intelligence.

Given the specific cultural moment we’re in, how has Covid-19 impacted your business? What strategies do you have in place to keep things moving along?

My business strategically partners with different youth serving businesses to offer our services. I thought I was about to crush it and have my phone ringing off the hook with this pandemic. Though that hasn’t happened (lol), business remains steady and there are new opportunities to serve more parents that I’m working on. To keep things moving along I continue to forge new relationships and deepen those that exist. I’m so happy that my relationships with CPS are deepening for us to multiply the number of parents we are training.

In a world of influencers, who influences you most?

Honestly, I remain most influenced by those who personally mentor me and Dr. King. I teach people of ways we can access mentors, even posthumously through their work.
Are there any books that have shaped your own character development?

I’m reading a book now; Connections over Compliance (Dr. Lori Desautels ). This book covers the importance for parents to regulate our own emotions to help kids cope with their situations. This has me thinking of regulating my emotions a lot lately and I’ve been really enjoying being reminded, in a fresh way, of this powerful tool.

What affirmations do you live by?

Les Brown – You gotta be HUNGRY
Eric Thomas – Be the Lion (hunter) and not the Gazelle (hunted)
Jim Rohn – Don’t say If I could, I would. Say, If I can, I will.
King – An injustice anywhere is a threat to justice everywhere

Describe a perfect weekend for you and your family?

The perfect weekend is when we are in sunny Florida in January (escaping the Chicago winter) in a swimming pool while the rest of our peeps are bundled in thick clothing. We love taking warm trips during the winter.

What’s your favorite meal?

Lou Malnati’s pizza, wings, and salad

If you could hear song performed live by any musician, what would it be?

Wow…Whitney Houston I will always love you…I’d cry!

What’s something people wouldn’t know about you?

Many people don’t know that I help education entrepreneurs to grow their businesses. This is one of my new enterprises I have a new excitement about.

Tell us about what’s next for Damien Howard?

Continue to grow as an investor to get more time freedom. With my time freedom I’ll be further empowered to do good in my city.

Thanks for the opportunity. Peace!

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