EPISODE 2
My Cyber Path, Part 1

MY CYBER PATH, PART 1

About this episode

In this episode, you will learn how Kip got into cybersecurity and what his career path was up this point.

Kip was involved with air-to-air missiles, firing them in ways that would test the limits of their capabilities and then turning the information that we collected about the firings into digital data and then serving that data up for scientists so that they could analyze what was going on. He had to learn how to protect systems and how to protect data and so I kind of backed into cybersecurity.

From the Air Force, Kip moved on to another mission and that was with the F-22 Advanced Tactical Fighter, which is a stealth fighter called The Raptor. When he was working on it, Kip served as the director of wide-area network security for a nationwide, multi-billion dollar program. During this time, Kip worked closely with defense contractors who were handling the software that made F-22 do all the fantastic things that it can do, as well.

When Kip left the Air Force, there was no such thing as broadband to regular homes, and most people were still on dial-up modems. Back then, cybersecurity was called computer security and then it morphed into network security, IT security, and then information security, before gaining worldwide acceptances under the term cybersecurity.

What you’ll learn

  • How to find passion for your work and your job?

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Episode Transcript

Kip Boyle:

Hi everyone, this is Your Cyber Path, the podcast that helps you get your first cybersecurity job. I’m Kip Boyle. I’m a husband, a dad, and I’m an experienced hiring manager of cybersecurity professionals. If you want to give me feedback on the show, or if you want me to answer your question on a future episode, please visit the show page at anchor.fm/yourcyberpath. When you get there, just click on the message button and start talking. 

On today’s episode, I’ll tell you my story about how I got into cybersecurity, what was my path, and why I stayed for years despite the stress and the constant threat of burnout. So today I work as a virtual chief information security officer. I really enjoy my work, but I mean a good question is why and how did I find my passion for my work, for my job? I reflected on this quite a bit as I prepared for this episode, and I realized it’s taken me a long, long time to be able to know the answers to those questions and to be able to actually find the words to share them with you, and I didn’t have the words to describe my first experience with computers but I really liked them from the first time I saw one at school when I was in ninth grade, and you’re probably going to laugh but it was a TRS-80 Model I, so that was a long time ago. The funny thing about that computer is I never actually used it because there were always these much older kids hogging the keyboard and I could never actually get any time with it. But I would stand there and I would watch them and just be completely fascinated.

So somehow, it’s just in my DNA to mess with computers, and understand how they work. But there’s another aspect of why I enjoy my work that’s less tangible, maybe less obvious. I’ve always had a big appetite for the feeling of safety and I think because of that, I was drawn to work related to protecting people and protecting things that were valuable, and I’m sure with reflection that’s due to the experiences that I had growing up. I just didn’t have the support system that a kid needs to feel safe most of the time. I had problems at home which caused me to feel insecure at school and pretty much everywhere I went, and as a result I found myself thinking a lot about how to avoid getting into trouble, and what’s funny is when I do that on the job today, I actually call that a pre-mortem exercise, and that’s part of the risk management approach that I bring to my work. 

Okay, so back when I was in high school and I saw that computer, so I thought about having some kind of a computer job when I got older. But the other part of me that was really interested in safety and protection also caused me to think about becoming a police officer. Well ultimately, I graduated from high school and I graduated from college, and I was commissioned as a second lieutenant in the U.S. Air Force, and that just felt very fulfilling to me. So here is where the cybersecurity part comes in. So while I was on active duty, I worked on the computer side of several secret weapons development systems projects.

The first one that I was involved with had to do with air to air missiles, firing them in ways that would test the limits of their capabilities and then turning the information that we collected about the firings into digital data and then serving that data up for scientists so that they could analyze what was going on. That project was as I said classified and so as I was doing the computer support for that mission, I had to learn how to protect systems and how to protect data and so I kind of backed into it, and I guess because of the things that I’ve already shared with you about how I grew up and what was on my mind, I actually enjoyed it. Just about everybody else I worked with thought it was annoying and difficult and they really wanted to minimize the amount of time that they spent dealing with it. But I actually liked it, and that was good for me because everybody said, “Great, Kip, you do it.” So I had my pick of things to do there. 

But eventually, in the Air Force, I moved on to another mission and that was with the F-22 Advanced Tactical Fighter, which is a stealth fighter, it’s called The Raptor, and when I was working on it, I was the director of wide area network security, and this was a nationwide, multi-billion dollar program. So we had defense contractors all over the place that were handling the software that made F-22 do all the fantastic things that it can do, and so I learned so much from that job as well. But I have to tell you, this was all before it was actually legal to sell things on the internet. So this was sort of at the dawn of the internet as a cultural phenomenon, as something that everyday people would use. The internet of course had been around for years and years before I showed up, but it was really just a niche thing that government and universities used, defense contractors, that sort of thing. 

When I left the Air Force, there was no such thing as broadband to regular homes. Everybody was still using dial-up modems and so that’s how I got into cybersecurity, so I backed into it basically. It was called computer security actually when I first started doing it, and then we started calling it network security and then more broadly we called it IT security and then information security, and now just about everybody calls it cybersecurity, except for some people who have been around in this career for a long time. They don’t like that word at all and I have to admit that it’s a fairly sensationalized term that we sort of got put upon us by media, Hollywood, that sort of thing. I didn’t really like it in the beginning but I’ve sort of stopped resisting and I just embrace it now. But these days, I’m doing pre-mortems all the time and working with customers, really enjoying it.

So there’s actually a bit more to my backstory but I’m going to save that for the next episode and soon another thing that I’m going to do is I’m going to start publishing an online course that’s going to help you get your first cybersecurity job. So you can help me and I would love to have your help. This is what you need to do. Tell me your number one question about getting your first cybersecurity job and please do that using my online survey. When you do that, you’ll get free access to the first edition of my four-week online class and that’s going to launch on April 6, 2020, and just for completing the survey, you’ll also get a free copy of my Amazon best-selling book, Fire Doesn’t Innovate: The Executive’s Practical Guide to Thriving in the Face of Evolving Cyber Risks.

Okay, so here’s how you can reach the survey. Go to b.link/cyberpath, that’s b.link/cyberpath, all one word, and please share this with anybody else that you think would be interested in completing the survey. I would really appreciate that. Okay, that’s enough for now. Next time I’m going to finish my story about how I got into cybersecurity and why I stayed despite the stress and the constant threat of burnout. So until next time, remember you’re just one path away.

 

Headshot of Kip BoyleYOUR HOST:

Kip Boyle
Cyber Risk Opportunities

Kip Boyle serves as virtual chief information security officer for many customers, including a professional sports team and fast-growing FinTech and AdTech companies. Over the years, Kip has built teams by interviewing hundreds of cybersecurity professionals. And now, he’s sharing his insider’s perspective with you!

Headshot of Jason DionYOUR CO-HOST:

Jason Dion
Dion Training Solutions

Jason Dion is the lead instructor at Dion Training Solutions. Jason has been the Director of a Network and Security Operations Center and an Information Systems Officer for large organizations around the globe. He is an experienced hiring manager in the government and defense sectors.