Season 2 Episode 83: Backwards Planning Your Military Transition with Jason Shockey

After serving 20 years in the United States Marine Corps conducting cybersecurity operations, Jason Shockey has successfully held 3 different chief information security officer roles in the private sector. While his transition may sound “easy”, a lot of hard work, careful planning and deliberate action has placed him at the top of the cyber industry. His methodical approach to his own transition and his desire to help others led him to create My Cyber Path, a resource designed to help students, veterans and HR departments successfully navigate a career in cybersecurity. Jason’s advice on mastering your mindset is relevant to anyone, regardless of career field.

About halfway into his military career, Jason began to focus on what he wanted for a career in the civilian sector once he retired. After researching job titles, he began to craft his own education pathway to prepare him for the qualifications he knew he needed. While he pursued his education, he was deliberate to apply the concepts he was learning to his duties in the military.

Jason believes luck is when preparation meets opportunity. Find a way to apply what you are learning for the future to your day job. By assimilating new knowledge and practicing repetition, real learning and practical application occurs. This is applicable to anyone, whether they plan to continue their military role in the private sector or plan to enter a new career field.

Jason discusses how his fear of not finding employment after the military motivated him to seek ways to stay positive and confident. First, you must believe in yourself. Figure out where you want to go and then work backward to craft a plan on how to get there.  For 8 years, Jason listened to motivational speakers and practiced visualization to keep his mind in the right place.

Reflecting on his roles in the military versus in the civilian sector, Jason believes the main difference is the way he interacts with people. In the military, rank dictates what a person knows, where they’ve been and how they are going to respond to you. That’s not the case in the civilian world. It’s important to be attuned to the people around you and know how you fit into the organization. You should be doing everything in your control to better yourself and the company. Although it may sound harsh, if you are not contributing to the organization and its mission, you are easily replaced.

For those considering a career in cyber, My Cyber Path matches interests and personality traits with cyber work roles and shows the pathway to get to that role through certifications, experience, training and education. It’s also a tool for the cyber professional who is ready to progress and grow into a more complex role. Jason has generously offered to give 10 people a complimentary lifetime access to My Cyber Path on the day this podcast is released. Please visit the Lessons Learned for Vets Podcast page on LinkedIn to learn how to take advantage of this offer!

Jason attributes his continued success and consistent growth in the cyber industry to his focus on personal excellence and the outcomes and outputs he produces for his employers. He also focuses on details and establishing small habits to increase his productivity. Jason discusses how what you eat, watch and listen to can all influence your success. Choose what you consume both in mind and body.

Please head to the Lessons Learned for Vets brand new YouTube channel at to hear Jason answer a bonus question that will leave you motivated.

You can connect with Jason Shockey on LinkedIn at

Learn more about My Cyber Path by visiting


SUBSCRIBE & LEAVE A FIVE-STAR REVIEW and share this to other veterans who might need help as they transition from the military!

Connect with me on Facebook and LinkedIn! Or check out our website at and listen to the previous episodes here!

Subscribe on Apple Podcasts

Click to Subscribe!

Subscribe on Spotify

Click to Subscribe!

Subscribe on Pandora

Click to Subscribe!

Subscribe on Amazon Music

Click to Subscribe!

Subscribe on Stitcher

Click to Subscribe!

Are You Struggling to Write Your Resume?

I created the Veteran Resume Self-inspection Checklist to lessen the resume writing struggle for veterans. This 11-item checklist will educate you in resume best practices while giving veterans a guide to assess their resume and determine if it's ready to send to  employers. 

Download Your Checklist Here