How Learning to Fly Made Me a Better Cybersecurity CEO

COMMENTARY

As a child, airplanes fascinated me — I was taken by their gravity-defying magic, their technical wonders, their sleek designs, and the adventures they unlocked. I dreamed of flying one myself.

Although I pursued a career in cybersecurity, flying always inspired me — so I chased my lifelong dream of becoming a licensed pilot. I continue to fly light aircraft in the little spare time I get alongside my role as the CEO of a leading cyber-risk management company. 

Always Have Backup

A recent experience prompted me to think more closely about the interplay between my two passions. 

Not long ago, I completed an advanced course for pilots of two-engine planes. Previously, I had only flown planes with one engine, which is a risk: If the engine malfunctions, you’re in big trouble. 

In the final training session, we practiced different responses in the event of an engine breaking down. As our instructor walked us through different tactics, one thought went through my mind: the critical need for a “defense in depth” approach to security. Just as the smooth functioning of an airplane relies on multiple mechanisms supporting one another, a modern cybersecurity platform also leverages numerous defensive techniques, so that if a threat slips through one layer, it will be caught by another. 

That was when I realized: While aviation and cybersecurity may appear as far apart as the heavens and earth, the skills I’ve learned from flying have profoundly influenced my career.  

Know Your Environment

Even at the beginning of my career, as a junior systems analyst and IT team manager, I understood that an organization’s cybersecurity posture is much broader than any single tool or platform. Effective cybersecurity requires a thorough understanding of the operating environment and all the tools therein. Before an organization can identify vulnerabilities and secure itself against attacks, it needs a complete understanding of its internal and external assets, digital surfaces, devices, brand assets, and more. 

Likewise, becoming a pilot not only required me to master the practical skills of navigating an aircraft through various conditions but also necessitated a deep understanding of the equipment on board. Flying without a confident grasp of my instruments or expected flight environment is like playing Russian roulette: potentially fine … or lethal. 

In cybersecurity, just as in aviation, one can never be passive. Full visibility into a technology environment is required to be able to manage risks, quickly adjust course, identify and communicate issues, and fix those issues under pressure. 

Continuous Learning and Testing

In the modern cybersecurity landscape, threats are always evolving, and hackers are constantly honing their skills. That’s why I ensure my company continuously tests its defenses and my employees constantly learn new skills to keep pace with the rapidly changing threat landscape. 

During a recent performance review with one of my direct reports, the employee suggested that some of our threat simulations and training sessions were so time-consuming that they prevented his team from carrying out other deliverables. I acknowledged that learning and testing take up a lot of time, but doubled down on the importance of learning from past incidents to understand future threats and tactics. A cybersecurity company that prioritizes this will serve its customers better in the long run, even if it means a routine report or product update will be slightly delayed. 

Muscle Memory and Task Execution

A little-known insight into a pilot’s mindset: When landing my aircraft, I barely think about what I am doing. That’s because I have practiced and repeated the same maneuver hundreds of times, making complex tasks feel like second nature. 

It’s just as vital to develop this sort of muscle memory among security professionals. Security teams should regularly practice routine protocols for any scenario. Conducting tabletop exercises and attack simulation drills allows teams to react quickly and effectively when a real threat emerges. 

By promoting constant preparedness, I aim to ensure that my teams can execute the best course of action without hesitation, even in high-pressure situations.

Small Issues Become Big Ones

After flying for a few years, I felt like I’d finally memorized the dozens of separate tasks that form part of a pre-flight checklist. In reality, I’d started to prioritize — I knew that I’d always have to check whether there was enough fuel in the tank to complete the journey, but making sure each seatbelt on the plane was fastened correctly seemed secondary. 

One time, I experienced a particularly bumpy landing. I asked a fellow pilot why that might have occurred, and he suggested checking the air pressure in the tires. I took a look and realized that I’d completely forgotten to check the tires before the flight. A tire low on air won’t cause the plane to fall from the sky, but landing on a flat tire can be extremely dangerous. If a flat tire hits the runway, it could burst and send the plane swerving. Incidents like this can easily be avoided — by running through the correct procedures to identify any small issue before it becomes a big one. 

In cybersecurity, small vulnerabilities in a system can easily be overlooked and are therefore ripe for exploitation. In short, cybersecurity is not just about responding to attacks — it’s about mitigating risks before they can cause damage. By implementing best practices and checklist procedures, security teams can do just that.  

The Sky’s the Limit

The lessons I’ve learned soaring through the skies have extended far beyond the runway. 

Learning from my mistakes and internalizing the discipline it takes to be a pilot have allowed me not only to lead my company with clarity and resilience; it also has provided me with a new perspective on the ever-evolving landscape of cybersecurity. Incorporating these lessons into the flight plan of my professional life has helped foster a culture of continuous improvement at our workplace, which ultimately has helped our customers.