The Best Job I Ever Had

“Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing.”

-Hellen Keller

In honor of Labor Day, I’ve been reflecting on my career in Cybersecurity and how I got here. I wasn’t always interested in security or even computers. When I graduated from college, I thought I wanted to be a stockbroker. I don’t know why. Looking back, I can’t say what it was that interested me about it, other than maybe the excitement related to being so close to the core of our financial system. During my senior year, I went to New York and interviewed with some companies, but I realized I couldn’t survive in NYC on what they were offering, so I went with my backup plan. I moved back home with my parents.

I got this temp job working at a telecommunications company. It wasn’t bad, and learning about technology came pretty easily for me. But in my spare time in the evenings, I was studying to get my license to be a financial advisor. I still knew nothing about investing, didn’t have a 401k, had never bought a home (remember I’m living with my parents at this point), and barely had a checking account. But I learned a lot about sales through a training program with a firm that wanted to hire me after I was licensed. After I got my license, I’ll admit I had started to get cold feet when I looked at all of the cold calls I was going to have to do everyday.

I was just a temp at my day job, and the director of the facility called me in. I had a 6-month contract and it was coming to the end of that time. There were lots of other contractors who had been there much longer, so I wasn’t worried. This was my cushion, my safety net, my backup plan. The director didn’t know I was thinking of giving up on being a financial advisor and thought I needed a kick in the pants to get out the door. So he let me know he thought I was a great employee, an asset to the company, but I needed to go pursue my dreams. So he fired me.

By that point, I had also worked my way up towards being a network engineer, so I shifted gears, buckled down, and got a new job where I could really focus on growing my skills. Did I mention I was still living at home?

I went on to do a lot of things. I worked for some startup tech companies. When those didn’t work out I went to law school to focus on my interest in open source software. I had done a lot of really interesting things, but I was still just dabbling here and there.

Have you ever felt like you had a lot of potential, if only you could find a way to unleash it? That was me. I was a hard worker. I spent most nights after work reading about technology or preparing for certification exams. I was building a foundation for a career, for a safe career, but I knew I could do something special.

A funny thing happened along the way. I started this job and instead of asking me to build a network (it had already been built) they asked me to break something. Technically speaking, they wanted me to set up a system to do ARP poisoning in order to allow users to register on the network. This was an open source product which would eventually turn into a NAC system. But I was blown away that after so much effort to understand how things worked, I realized how interesting it was to break them.

I was talking to a cybersecurity expert recently and they said something weird. They said aside from maybe being a rock star or an astronaut, there isn’t another job in the world that they would want to be doing instead of cybersecurity. My brain started processing this, and it took about a week before I realized I agreed with him. I can’t imagine doing any other job in the world.

I did eventually move out of my parent’s house. I went to law school. I wrote books. I started doing public speaking. What is so special about my career in cybersecurity is that, looking back on it, it’s been an adventure. I get to help protect people. And when things don’t go right, I get to help them through it. There’ve been twists and turns and surprises. Perhaps the most surprising thing of all, it’s been the best job I ever had.


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