A Career in Cybersecurity? Advice from a CISO.

Oct 20, 2021 | Security, Solutions

One of the great things about the way the cybersecurity community has matured in recent years is the openness and willingness to provide mentorship and assistance to newcomers to the field. The number of offers for advice, resume reviews, study guides and other assistance that I see in various social media and other forums is incredible! But why the change? Because we, as security professionals, know firsthand that if we want to get ahead of the curve, we need all the help we can get. The timing could not be better to dive headfirst into the rewarding career of cybersecurity.  What I hope to do in this quick blog post is to give a bit of knowledge on the career of cybersecurity for both the career seeker and the hiring manager!

Degree versus Certs versus Real-World Experience.

The most common question that I get when I am asked about a career in cybersecurity is the best path to choose… degree, certifications, or real-world experience. I think this is one of the hardest things about choosing to transition into this field. The answer is not a simple one and it is not “one size fits all”. What I typically say is that there is absolutely no replacement for real-world experience. Dealing with normal, everyday user issues or complex and imperfect scenarios that exist outside of a lab environment – and in some cases failing miserably and then finding the right solution to bring it all back together after grueling time spent troubleshooting – prepares you for the worst that the world of cybersecurity can throw at you. Also, having the empathy that a security control that should be put in place could cause undue stress in an already stressful environment and may be the perfect scenario for some other, less restrictive controls but still meet the goal. These types of scenarios can only be found by having real-world experience. Experiencing this gives us thoughtful, knowledgeable, and engaged cybersecurity professionals. Depending on the organization that an entry level person can discover a role within, you can find yourself getting tunnel vision. This limits your growth by solely focusing on the daily tasks at hand rather than getting a wide breadth of knowledge of all topics within a subject.

With that in mind a great place to get the additional information that real-world experience may prevent is by studying on a degree path or within certification programs such as ISC2, CompTIA, EC Council, SANS, and others. These methods, while typically only providing cursory amounts knowledge about a given subject, allow you to explore different ideas, best practices, and new technologies that may sit outside of the typical workday. So, my answer to this question becomes a very drawn-out discussion about how a person learns, how they like to spend their time, and what the timeline for transition may look like for each individual person exploring this career.

Now I feel that I must mention another excellent resource at your disposal. The internet has a vast plethora of free and or very cheap resources that allow you to gain the knowledge that a traditional certification path or degree program may provide but allow you to apply the techniques learned in an active learning environment. Websites such as hackthebox.com or tryhackme.com are some examples of some relatively cheap resources that give training and hands-on experience.

Another great resource for those with some technical experience in IT and looking to transition into cybersecurity is testout.com.  For job seekers and hiring managers alike, this can be a great tool.  For the job seeker, you can show that your knowledge in a particular capability is up to par with industry certifications without requiring expensive exams and boot camps. For hiring teams, you can know that the candidate has a validated baseline of knowledge that can be used to fit them into a new role that may not be something they have done in the past.

Choose your own Adventure.

So, you’ve chosen a path and have decided how you’re going to explore the world of cybersecurity but you don’t know where you want to go.  The best part about cybersecurity is the extreme number of things that you can learn and do within this field. If you love the idea of an endless supply of exactly the same task, working with structured data, and piecing 100 data points together to come to a conclusion, there is a place for you.  If you need a very dynamic workday where you’re moving from topic to topic and providing feedback on how to accomplish very different goals, there is a spot for you.  If you’re the kind of person that just loves to write documentation and match a specific requirement to its technical control… yep… there is a spot for you.  And last, if you just want to see how quickly and effectively you can break (or break into) systems then provide options to solve the problems you exploited, there is a special place for you.

My point is that everyone is different and there is no single way to get into cybersecurity.  Blue team, red team, purple team, white team are all options to take, and we need members of every sort of team to make security work effectively. So, find that niche that you like. Find that role that makes you want to get up early in the morning and late into the evening to satiate that passion and make a career out of it!  There is space for everyone to choose their own adventure and make the journey their own!

Variety is the spice of security life!

Finally, after saying all of that, it is important to understand how we can improve this career field and reset our own expectations of what makes a great security professional. Because there are multitudes of different paths to follow to achieve an “education” in cybersecurity and there are unlimited types of roles to fill within this field, we can safely assume that it takes all kinds of people to make it happen. The only way to solve the reported cyber skills shortage is to take a step back and understand that there is no one way to do so. We need a large array of experiences and skillsets outside of the traditional IT and cybersecurity skillsets to bring cybersecurity programs to the masses and to make our information security programs something that can be adopted by everyone from the bookkeeper to the salesperson to the most technical network engineers. So, take a second when navigating careers in cybersecurity, whether seeking or hiring and find those skills that can bring a benefit to the team in a new, fresh way.


Steve Sim
VP, Security & CISO
Green Cloud Defense


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