TL;DR
Recently, we got some useful advice from a Cybrary learner just beginning his cybersecurity journey. While his thoughts are well worth a read for anyone in the field, whether novice or experienced, I thought it would be interesting to pair them with those from someone who’s been in the job for longer. Much longer, in fact.
Meet Hugh Shepherd. After working in the US Army Signal Corps (the branch responsible for communications) back in the 90s, Shepard transitioned to the private sector and began working as a consultant across the then-burgeoning IT industry. This gave him a front-row seat to watch the convergence of telecommunications and networking, the rise of wireless and broadband technology, and the emerging dominance of smartphones. It also gave him the opportunity to do a lot of different things, “be it wireless telecom, be it data centers, you name it,” he said.
And this included cybersecurity, a field Shepherd has focused on exclusively for the past decade. Currently, he works as an advisor and consultant for organizations in need of strategic cyber security services and training, as well as a Quality Engineer for Cybrary courses. I chatted with Shepherd to learn how his experiences have shaped his view of the industry and to see what kind of tips he had for anyone else in the field. Here’s what he had to say.
Want to stick out? Then stick your hand up.
When it comes to career advice, Shepherd was clear: One of the most effective ways to stand out from your peers is to do the work no one else wants. “Be willing to do the hard stuff, put yourself out there,” he said. “Be the guy who will step up and come in on the weekend or stay late after work.” And this isn’t just advice that Shepherd had heard — he’d personally experienced the benefit of it.
Back in 2015, Shepherd told me, before he’d transitioned solely to cybersecurity, he was working on a project for AWS that involved building a cloud environment and migrating a server. But when they needed someone to help make the new system secure, no one wanted to do it. “Believe it or not,” Shepherd said, “no one wanted to do cybersecurity work at that time.” So Shepherd raised his hand.
He was quick to mention that this was not the cool “hacker in the hoodie” kind of security work. Instead, it was a “very tedious process” that anyone familiar with the slow assessment work of system hardening will know. But they got through it. Afterwards, his project manager said he was their security guy now. “And that was my entry into cybersecurity,” he said.
Since then, Shepherd has used this initiative to carve a successful career in the industry. “Volunteering has been very beneficial to me,” he said. “It’s a great way to get your name out there, you know, get your foot in the door, or at least expand your network.” As it turns out, it’s also how he got his current role with Cybrary.
Become a member or attend an event
Speaking of networking, despite its importance for career development, this can be something that can feel notoriously hard in cybersecurity and other computing fields. This is especially the case for those just getting started. The subject of our last article, Forrest Caffray, even mentioned this challenge specifically: “I wish there was some, I don't know, some way of encouraging [more] networking,” he said. “It's quite tricky. It's quite hard to network or find others.”
For Shepherd, however, there’s an additional obstacle. His wife’s job has taken him and his family far from traditional tech hubs and put him in places such as Nepal and Thailand. But while this may have proved isolating for some, it has only underlined the importance of joining organizations, attending events, and getting involved however he can.
“Being a member of some of the organizations out there that are IT or security focused, be it ISC2, CompTIA, ISACA, or the countless others — all of them are a great opportunity to get out there and connect with people,” he said.
Shepherd acknowledged that doing this regularly can be difficult. “I attended several recently when I was back in Thailand,” he said. “I went to like three in two months. It’s kind of a hassle sometimes, but it’s well worth it. I connected with a lot of people and learned a ton.” He added that, later on, when you cross paths with someone who works in the industry, these events will give you something relevant and interesting to talk about.
“It shows that you’re engaged and that you’re committed to continuous learning,” he said. In other words, it’s another way to help you stick out.
Keep following your passions
While networking and attending events can make gaining knowledge and connections seem like something you only do to advance your career, Shepherd closed our conversation by emphasizing how important it is to keep pursuing whatever you’re most interested in. “Identify the area of cybersecurity or IT that you're passionate about and just fully embrace it,” he said.
Although he pointed out that beginners need to first make sure to spend time getting prepared and broadening their knowledge by learning the fundamentals of the industry, once you decide on your specific career path it is vital that you love what you’re doing. “If you're not enthusiastic about it,” he said, “or it gives you a headache, then maybe it's not the career path for you.”
Shepherd added that, when you’re interested in what you’re doing, when it’s actually something you enjoy, then it will be much easier to stay on top of all the changes in the industry — which is essential for anyone interested in a long-term career. And even then it can still be difficult. “I can't stay on top of all the different news, different developments,” he admitted. “But, you know, I try my best.”
More importantly, he’s having a blast, which is a big reason why he’s been doing it 20-plus years.
Start your path here
I couldn’t help but notice how Shepherd’s last piece of advice mirrored Caffray’s recommendation from our previous article to “be patient” and “have as much fun with it as you can.” It felt like we’d come full circle in a way. But it also felt like we’d hit on something fundamental: although you’ll be sure to encounter your fair share of challenges as you begin your cybersecurity career, the only people who will succeed are those who fall in love with it. And to do that, it helps to get started out on the right foot.
Ready to start your journey? Browse through our catalog or request a demo for your team to begin accessing our extensive curriculum. We may just help you fall in love.
