Cybersecurity Careers. PHOTO: Cybercrime Magazine.

No Shortcuts To Mastering Cybersecurity

Know yourself, know technology, and know business

Jason Shockey

Morristown, New Jersey – Nov 27, 2020

Cybersecurity mastery is achieved when someone has acquired the experience, knowledge, and judgment from deliberate practice honed through years of apprenticeship. There are three main attributes resident in all masters: Obsessive curiosity, lifelong learning, and innovation.

The attributes might seem simple at first but become difficult over time because they involve delayed gratification, a concept most people are uncomfortable with following.

Many people believe they cannot achieve mastery because the tasks are too difficult but that’s not the case. What usually happens is people don’t understand themselves enough before they begin their journey to mastery. They might ask difficult questions about themselves but they don’t really want to know the answers to then make corrections.

Trait-based cybersecurity career pathways match a person to a specific cyber work role and show them the path toward cybersecurity mastery. These pathways are the best way to get people through to mastery and consistently demonstrate the three attributes. Trait-based cybersecurity career pathways show people the correct type and sequencing of existing certifications, experience, training and education to pursue relative to a person’s perfectly matched cyber work role.

Demonstrating the three attributes and using trait-based cybersecurity career pathways gives people deeper job satisfaction and the highest chances of career success, and gives us the greatest probability of closing the global cybersecurity workforce gap.

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Curiosity makes you interested in things. In our youth we were curious to find new things and interested to see how they worked. This urged us to pursue knowledge about those interests. Over time, we built our knowledge base and this created momentum to gain more knowledge and question concepts on a deeper level. The repeated cycle of curiosity, question, knowledge is a large part of cybersecurity masters.

Many people’s curiosity starts strong early in life and fades quickly, which stunts their journey toward mastery. A person who attains cybersecurity mastery has the ability to maintain their curiosity level throughout their life. This allows them to continually grow.


Time effortlessly flows when a master is at work. They don’t feel like they’re working. Anyone can get to this point. Anyone can achieve mastery. The best way is by learning through deliberate practice and applying what you learn through apprenticeship. Be ready and welcome harsh criticism for your work since you want to produce the highest quality. Don’t be offended by a critique, use it to make you better.

When learning cybersecurity, keep in mind Richard Feynman’s statement, “Know something, don’t just know the name of something.” I first came across Newton’s Telecom Dictionary and its thousands of entries in 1999 when I started in IT.  Since I was new, I started memorizing the dictionary terms so I could better participate in meetings. I learned a valuable lesson that knowing the terms from the dictionary gets people’s attention but they’ll quickly turn away from you if you don’t provide meaningful input about the term. Know hundreds of terms but also know how and when to apply those terms for a business benefit.

If you’re pursuing cybersecurity mastery, then what you’ll need to learn falls into three categories — know yourself, know technology, and know business. For awareness, Brian Kreb’s lists skills that cybersecurity insiders consider useful. Keep in mind his list covers a portion of one of the areas you’ll need for cybersecurity mastery.


Masters have the ability to make surprising and creative connections between ideas. They have the ability to see what others cannot see. Through years of rigorous, deliberate practice and application through apprenticeship anyone can achieve cybersecurity mastery.  As you reach the level of cybersecurity master you will then innovate.

You’ll start to innovate along your journey but at your highest level, you’ll command innovation. At this level you will continue to challenge yourself and challenge the established thought in cybersecurity. Your contributions, your questioning of deep-rooted industry thought will change and grow the cyber industry for the better.

A difficult situation is to know when you’ve reached cybersecurity mastery. I found myself in this situation when I decided to launch to help people achieve cybersecurity mastery and close the cybersecurity workforce gap. For two years I aggressively tried to prove my idea wrong and that didn’t happen so I decided to launch. Neil deGrasse Tyson said it best, “One of the great challenges in life is knowing enough about a subject to think you’re right, but not enough about the subject to know you’re wrong.”

Finding Your Pathway 

The most efficient way to achieve cybersecurity mastery is by using a trait-based cybersecurity career pathway. These pathways match a person to their perfect cyber work role and show them how to enter the cyber industry and level up throughout their careers.

Being matched to a cyber work role based on personality traits gives people the deepest job satisfaction and the highest chance of career success because they’re matched to the daily rigors of the job roles.

To get started on your journey toward cybersecurity mastery you must first know yourself according to the Big 5 Model. Then, how do your personality traits relate to the 12 cybersecurity work roles in the LISTO framework? Next is to get a personalized career pathway that will guide you from your starting point all the way to cybersecurity mastery.

When you’re beginning in cybersecurity expect to feel foolish since you won’t be able to perform the work correctly on the first try but eventually you’ll get there. “If you’re not willing to be a fool, then you can’t be a master,” said Jordan Peterson. Instead of expecting to be perfect, expect to make progress toward perfection.

Be prepared to sacrifice common comforts in your pursuit of cybersecurity mastery. Conor McGregor revealed a secret of the world when he said, “There is no talent here. This is hard work, this is an obsession. Talent does not exist. We are all equals as human beings. You could be anyone if you put in the time. You will reach the top and that’s that. So, I am not talented. I am obsessed.”

Robert Greene said in his book Mastery, “The future belongs to those who learn more skills and combine them in creative ways.”

There are two mistakes that all people make when trying to achieve mastery, not starting and not going all the way. I believe there is a spot for everyone on the cybersecurity team. I invite you to get started on our journey toward cybersecurity mastery and go all the way.

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– Jason Shockey is the founder of Prior to founding My Cyber Path he served as the Chief Information Security Officer at a publicly traded company in the greater New York City area. Prior to his CISO role, Jason served 20 years active duty in the US Marine Corps as a technology leader conducting cybersecurity operations, incident response, and cyber risk management.

About My Cyber Path

Get A Pathway, Get a Job for Life!

My Cyber Path uses a proprietary algorithm to match you to one of 12 cyber work roles in Leadership, Intelligence, Supporting Technology, or Operations.

Get a career pathway showing the right sequence and type of certifications, experience, training, and education required for your perfectly matched cyber work role.