Meet Jason Brooks

 

We’re excited to introduce you to the always interesting and insightful Jason Brooks. We hope you’ll enjoy our conversation with Jason below.

Jason, we’re thrilled to have you on our platform and we think there is so much folks can learn from you and your story. Something that matters deeply to us is living a life and leading a career filled with purpose and so let’s start by chatting about how you found your purpose.

For nearly two decades, I woke up every day with crystal-clear purpose. I was a teacher, finding joy and fulfillment in helping young people discover themselves and the world. But one day, that certainty shattered.

I’ll never forget walking into my Brooklyn classroom, doing a routine homework check, and feeling *off.* At first, I thought it was just a cold, the flu, or maybe seasonal depression. But that moment marked the start of a 12-year journey through profound loss, reinvention, and transformation.

Desperate to find meaning in the second half of my life, I interviewed hundreds of elders, seeking their wisdom. Nights of frustration and tears eventually revealed a truth I had overlooked: I’d always been intrapreneurial as a school leader—organizing conferences, fundraising, and driving initiatives—but fear had held me back from fully embracing my entrepreneurial side.

Through discernment, I saw how I’d missed opportunities to explore entrepreneurship, blinded by my own doubts. Now, having done the hard work, I’m profoundly grateful.

To anyone struggling with purpose: keep going. There will be moments—maybe this is one of them—where you feel lost or discouraged. But your path is where you’ll uncover your purpose. Don’t give up. Keep walking.

Thanks, so before we move on maybe you can share a bit more about yourself?

I was born and raised in Watts during the height of the War on Drugs. One summer, I took a test that changed my life, landing me at an all-boys boarding school in Claremont, California—a shift that felt like going from the ‘hood to Hogwarts.

From there, I spent nearly two decades teaching, helping students discover their potential. After leaving formal education, I launched two companies dedicated to teaching people how to recognize, change, and improve linguistic patterns. Now, I work with leaders to uncover hidden linguistic dynamics, rework them, and use communication to transform their businesses.

I believe everything we strive to achieve ultimately comes down to communication. The ways we communicate can make or break not only our professional success but also our personal lives. I’m passionate about blending psychology, technology, and the science of linguistics to help leaders unlock their potential.

After much reflection (and some resistance), I’m now launching a communications training company specifically for early-career leaders. The goal is to help them communicate effectively and use language strategically to advance their careers. This work excites me because it empowers the next generation of leaders to achieve success through the power of words.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

1. Learn Constantly: Keep expanding your skillset and knowledge—continuous learning is essential for growth and success.

2. Persist Through the Struggles: There will be moments when it feels impossible, even soul-crushing. But if you keep moving forward, step by step, you’ll emerge stronger and find yourself in a new, more beautiful place.

3. Leverage Your Expertise: Identify what you excel at that others find challenging. Build a lead so strong it’s hard to compete, positioning yourself as the go-to expert in your field.

Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?

The most impactful thing my parents ever did for me was to have the courage and foresight to send me away to boarding school. Their humility in trusting other adults to help raise their son from ages 14 to 18 remains one of the greatest gifts I’ve ever received.

Attending a single-sex school was exactly what I needed as a young man. Coming from a family with four sisters, I craved male companionship and found it at Webb. Beyond friendship, I was surrounded by countless examples of what it truly meant to “be a man.” These weren’t the stereotypical, surface-level tropes but genuine examples of humble leadership and care.

One that stands out is my high school basketball coach. Every Monday and Thursday, the entire school gathered for a formal dinner, sharing a five-course meal. I was fortunate to be seated at my coach’s table, where we bonded over sports and life. One evening, his pregnant wife experienced severe morning sickness at the table.

While the reactions from a group of high school boys ranged from awkward to immature, it was my coach’s response that changed my view of masculinity forever. Without hesitation, he tried to catch her vomit with his bare hands. When that failed, he removed his shirt and tie—right there in front of 400 students, peers, and superiors—and used them to clean up the mess.

He then stood tall, bare-chested, and escorted his wife out of the dining hall with unwavering pride and care, holding her close as they returned to their home. I remember thinking, *that’s what it means to be a man.* Not bravado or ego, but humility, service, and the willingness to lower oneself to protect and support the people you love.

That moment has stayed with me, shaping how I view true leadership and masculinity.

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