Lessons from Cybersecurity and the Open Water
I’ve always been drawn to the water. Growing up near the coast, it was a constant backdrop to my childhood, a playground and a place of wonder. But until recently, I had never truly ventured into the world of sailing. Despite my familiarity with the water, learning to sail has felt like stepping into a completely new domain—one filled with equal parts excitement and trepidation.
It’s an experience that has brought me back to the early days of my journey in cybersecurity. The parallels between the two are striking. Both require a willingness to embrace the unknown, to face fears of making mistakes, and to accept that growth often comes with a healthy dose of discomfort.
The Fear of Looking Foolish
When I first started exploring cybersecurity, I constantly worried about doing something wrong. Whether it was configuring a firewall or testing a new system, the fear of looking foolish—or worse, accidentally causing harm—was ever-present. In sailing, that same fear crept in the moment I took the helm of my newly purchased Catalina 34. What if I make the wrong move? What if I’m not as prepared as I think? What if I end up embarrassing myself in front of experienced sailors?
Both pursuits have taught me that mistakes are inevitable. The key is not to let the fear of failure paralyze us. Instead, it’s about learning from every misstep and moving forward with a little more confidence each time.
Respecting the Rules
In cybersecurity, the consequences of crossing legal or ethical boundaries can be severe. Early on, I was acutely aware of the fine line between ethical hacking and breaking the law. Understanding and respecting those boundaries became a foundational part of my career.
Sailing, too, has its rules. There are regulations, navigational norms, and unspoken codes of conduct on the water. Ignoring them can lead to dangerous situations—not just for myself but for others as well. Both disciplines require me to operate with integrity, knowledge, and a deep respect for the systems at play.
The Thrill of Discovery
One of the most rewarding aspects of both sailing and cybersecurity is the sense of discovery. In cybersecurity, uncovering vulnerabilities or finding elegant solutions to complex problems brings a rush that’s hard to describe. Sailing offers a similar thrill—charting a course, feeling the wind catch the sails, and seeing the world from a perspective few get to experience.
This journey has reminded me that the excitement of discovery often outweighs the fear of the unknown. It’s about trusting in my ability to learn and adapt, whether I’m navigating a network or the open water.
Embracing the Journey
As I prepare for spring and the opportunity to take my Catalina 34 out on the Chesapeake Bay, I’m reminded of how far I’ve come since those early days in cybersecurity. Both journeys have taught me that growth happens when you’re willing to step outside your comfort zone. They’ve shown me that while fear is natural, it’s not an obstacle—it’s a sign that I’m about to do something worthwhile.