Commanding Officer and CISO: Two jobs I decided against

One of the best ways to grow is to surround yourself with wise men. I have been lucky in this regard. 

At the ripe age of 18 I left home for the comfort of US Navy boot camp. To understand that statement, you would need to understand growing up in my home. That is a story for another time. After boot camp, I was lucky enough to have a successive string of mentors and influencers that led me to success. 

One such person was LtCdr Gray, Officer-in -Charge at RAF Digby, UK. At this point in my career, I was facing a career decision. Stay in my current job and try to make Chief Petty Officer or submit my Officer Candidate package. Mr. Gray sat me down for an interview like many others before him had done. This one was different. He asked if I had thought about leading Sailors into battle. I responded with the typical male bravado of someone who had been in these interviews before. Then he said, "Have you ever thought about sending someone to their certain death while you stayed behind?" This was a question like I had never had before. He sent me home to contemplate that question. It changed my life. I went on the become a Chief and never gave the Officer community another thought. I takes a special person to assume the burden of command. Many nights he worked to ensure the best quality of life for his Sailors, knowing that, at any time, he may have to deploy someone halfway around the world to support a mission in a desert. A mission that few Sailors train for, desert combat.

The second person who changed my life was my boss and great mentor in the civilian world. He took a chance on me knowing that I had 20 years of cool experiences and had done really good things, but my resume was a mess (most transitioning military personnel are in the same boat). Over 3 years he sat me down several times to talk about my work and my future. One one such occasion, I told him I wanted to be a CISO. I asked if he could put me on a path to do just that. He explained to me these two things:

     1. A CISO can do everything right (within the constraints of the business, of course) and still suffer a breach

     2. If your company is breached, it is your fault. 

These words (and his daily stress) are what changed my mind about that career choice too.

Being happy in life comes from understanding what you need, what your strengths and weaknesses are, and from surrounding yourself with wise council.