From School Pranks to Boardrooms

Navigating from a school computer lab to a boardroom wasn’t a straight line, but it’s a path more accessible than people might realize. I’m going to walk you through my journey, hoping you’ll see how attainable each step can be, even when the path is filled with unexpected choices and transformative moments.

I’ll admit, I hesitated to share this story, concerned it might come across as self-promotional. But I realized that if my non-traditional journey offers hope or inspiration to anyone feeling boxed in by societal expectations, then it’s worth sharing. While my path leans into IT and cybersecurity, the broader theme of forging one’s own way is universal.

Chapter 1: Humble Beginnings

Success isn't a one-size-fits-all journey. Let my story be a testament to that.

The Elementary School Prank

The seeds of my love for technology were planted in elementary school. One playful day, I discovered the magic of the "Net Send" command, leading to a memorable prank that, while mischievous, unveiled my fascination with computers.

High School: Mentorship Matters

High school saw my passion for technology evolve. Working in IT consulting alongside my brother, I understood the beauty of mentorship. I am eternally grateful for this period—it laid the foundation for my future endeavors.

Chapter Insights: Life's early stages taught me the importance of hands-on experience, the potential risks of technology, and the unmatched value of mentorship.

Chapter 2: A Leap of Faith

Life is filled with pivotal decisions, and the paths we choose can profoundly shape our future.

The Military Transition

In 2005, I enlisted in the United States Air Force (USAF), a decision that reshaped my life. The USAF not only honed my discipline but also helped me overcome a personal challenge: a speech impediment. With the support of my peers and the military's structured environment, I found my voice. The relationships I built during this time remain invaluable to me. This networking, combined with the USAF's tech-intensive training, deepened my passion for cybersecurity. Amidst my military commitments, I found love, marrying my wife, and welcoming two boys into our lives, further enriching my journey.

A Turning Point

During my time in the military, our firstborn began showing unique developmental challenges. While the military's healthcare was robust in many aspects, it struggled with rare conditions. For two years, we faced an uncertain medical journey, navigating a condition that made everyday tasks more challenging for our son. The military's suggestion to place our child with stateside family for us to fulfill our duties became the tipping point. Recognizing our family's evolving needs, we decided it was time for a change. With our son's best interests at heart, I began preparing for a transition outside the military.

Certification Pursuit

As my USAF chapter neared its end, I set my sights on the CISSP certification—a crown jewel in cybersecurity. Many advised against pursuing this rigorous certification so early in my journey, suggesting it might be a leap too soon. But, fueled by an inner drive and understanding the stakes at hand, I chose to defy the conventional wisdom. I committed myself to the challenge, pushing harder than I ever had before. My initial attempt narrowly missed the mark, but rather than deter me, this setback only intensified my resolve. A month later, with unwavering determination, I achieved this milestone.

Chapter Insights: This chapter of my life taught me the strength of resilience, both in confronting personal challenges like my speech impediment and navigating the unique needs of my family. The bonds formed during military service underscored the value of deep connections, both professionally and personally. The USAF not only honed my technical skills but also instilled in me the importance of adaptability and prioritization, especially when faced with life-altering decisions.

Chapter 3: Embracing the Private Sector

Every journey has its twists and turns, and my foray into the corporate world was no exception.

Rackspace: A New Adventure

Transitioning from the disciplined environs of the military, I stepped into the vibrant, fast-paced world of Rackspace, armed with my recent CISSP certification. Rackspace was more than just a tech company; it was a melting pot of innovation and creativity. The headquarters, once an old mall, had been transformed into a state-of-the-art office space—each corner designed to inspire, from the art-adorned walls to the ingenious collaborative spaces.

The camaraderie at Rackspace was unlike any I'd experienced. From the interview itself, I felt less like a new recruit and more like a family member being welcomed back home. The team's spirit, commitment, and passion for technology were palpable, making every project feel like an adventure.

Yet, as with any journey, there were challenges to face. Despite my deep appreciation for the company's culture and mission, real-world considerations—primarily financial constraints—loomed large. Balancing my dedication to Rackspace with the growing needs of my family, I made the difficult decision to move on after just one enriching year.

Chapter Insights: Rackspace taught me that a company's culture can be as important as its mission. The energy, passion, and sense of community can make even the most challenging tasks feel rewarding. However, it also underscored the importance of balancing professional passions with personal responsibilities. Sometimes, difficult decisions must be made for the greater good of one's family, even if it means leaving behind a place you love.

Chapter 4: Entrepreneurial Tides

Entrepreneurship is often likened to a journey on unpredictable seas—calm waters can suddenly turn stormy, and unforeseen challenges can test even the most seasoned sailor.

Consulting Chronicles

Jumping into the world of consulting, I found myself immersed in a rich tapestry of experiences. Each project was a new learning curve, a challenge to tackle, and an opportunity to make an impact. My days were filled with accomplishments, brainstorming sessions, and hands-on work. However, like any journey, it wasn't without its pitfalls. Mistakes were made, lessons were learned, and over time, I felt the pull to move in a different direction.

Openly Secure: A Vision and a Venture

With a dream to revolutionize the cybersecurity landscape, I founded Openly Secure. The vision was clear: to create a hub where cybersecurity knowledge could be freely shared, eliminating the redundant efforts I had witnessed across various clients. I envisioned Openly Secure as a knowledge reservoir and a launchpad for a robust consulting business.

The passion and energy I poured into this venture were unparalleled. Late nights, brainstorming sessions, and relentless dedication became the norm. However, the journey also unveiled a profound realization. When a deeply held passion becomes the primary means to provide for your family, the lines can blur. The pure joy of passion can sometimes be overshadowed by the weight of responsibility.

Chapter Insights: From my consulting days to the inception of Openly Secure, the journey reinforced the value of adaptability, continuous learning, and the delicate balance between passion and profession. The most poignant lesson, however, was understanding the dynamics of pursuing a passion when it's intricately linked to one's livelihood.

Chapter 5: Back to Enterprise

The entrepreneurial realm had been a whirlwind of experiences. Yearning for a different challenge, I was drawn back to the allure of the corporate world.

New Beginnings at HPE

Post-entrepreneurship, the job hunt was a journey in itself, culminating in two standout options: USAA and Hewlett Packard Enterprise (HPE). While both were tempting, HPE's varied work challenges, attractive compensation, and the prospect of collaborating with a dynamic team made the decision straightforward. I was set to be a part of HPE's renowned security consulting division as a Security Architect.

Turbulent Times at DXC

Life at HPE was a rich blend of learning and collaboration. However, the merger with CSC to form DXC Technology brought about seismic changes. Recognized for my contributions, I was promoted amidst this flux. Yet, the merger came with its challenges: swift workforce reductions and a strategic shift. Many colleagues transitioned out, and sensing the shifting sands, I too began contemplating my next move.

Immersed in a vibrant ecosystem of tech enthusiasts and seasoned professionals at Hewlett Packard Enterprise (HPE), every project was a treasure trove of learning. However, the corporate landscape shifted dramatically when HPE merged with CSC, giving birth to DXC Technology. This new entity was not just a change in name or branding; it represented a seismic shift in the company's direction and strategy.

Chapter Reflections: This chapter of my life reinforced the essence of adaptability in the corporate world. It highlighted the significance of seizing growth opportunities while being attuned to changing landscapes. Success in such an environment requires both embracing evolving roles and knowing when to carve out a new path.

Chapter 6: Leadership

The trajectory of growth often leads to leadership, where the challenges are more intricate and the stakes, higher.

A New Horizon at Aon

The year 2019 ushered in a new chapter at Aon. As I integrated into the company, my dedication, and the diverse experiences I brought to the table, propelled me through a swift ascent. From taking on managerial roles to leading teams and projects, each step was a testament to the power of perseverance and vision.

Today, in my role as Vice President, Sales & Solutions Enablement, I am not just executing tasks but shaping strategies. I'm at the nexus of decision-making, playing a pivotal role in influencing the company's direction, fostering innovation, and making impactful contributions. It's a position that demands both a macro and micro understanding of the business, and every day presents opportunities to learn, inspire, and lead.

Chapter Reflections: True leadership transcends job titles. It's a synthesis of mentoring emerging talent, sculpting strong and cohesive teams, always putting the client's needs at the forefront, and being agile enough to navigate the ever-shifting business terrains. Being at the helm means constantly evolving, learning, and setting the pace for others to follow.

Epilogue: Lessons from a Journey Less Traveled

My story might be unique, but it's one among many. Forge your path, embrace change, and remember—your unique journey is your story's essence. Always maintain a positive and hopeful outlook, even when faced with adversity.

What are key takeaways?

• Embrace real-world experience. It often rivals formal education.
• Professional certifications can be game-changers.
• Stay adaptable, resilient, and ready for challenges.
• Leadership skills can be honed through practice and experience.

I owe much of my progress to key influences and mentors. A heartfelt thank you to Beatrice Conner and George Mengelberg for their steadfast support and insights. Their mentorship has been pivotal in my journey, and I hope their dedication inspires others to guide and uplift those around them.

Disclaimer: The views and opinions expressed in this article are my own and do not reflect those of my employer. This content is based on my personal insights and research, undertaken independently and without association to my firm.