How I Would Strategically Transition from the Military into Cybersecurity

If I could rewind to the day I was separating from the military and start over knowing what I know now, this is exactly how I would approach getting into cybersecurity.

Not randomly.
Not chasing whatever certification was trending on social media.

But strategically.

Cybersecurity is one of the best post-military careers available, but only if you approach it with a plan.

Here’s the plan I would follow.

Step 1: Pick a Domain

Early on, I made the same mistake most transitioning service members make:

“I want to work in cybersecurity.“

The problem with this statement is that it’s too broad to be useful.

This is a great visual breakdown of the cybersecurity domains provided by StationX (https://www.stationx.net/cyber-security-domains/).

This image is just breaking the surface on how large an ecosystem comprises “cybersecurity“.

Out of all the potential career paths that define these different domains, what needs to be understood is that each of these careers look entirely different day-to-day with their trajectories.

Once I understood that, everything changed.

My Advice

Spend a few weeks exploring domains before committing:

• Watch subject matter experts (SMEs) and practitioners on Youtube.

• Connect with individuals already in your targeted domain on Linkedin and ask for their insight (we will revisit this later).

• Join Discord or Slack groups targeting the domain you are interested in and post questions to the members.

After doing this, then pick ONE.

You do not have to marry it forever, but you need direction.

Focus on building momentum.

Step 2: Reverse Engineer the Job Market

Before ever studying for a single certification, I would research job listings.

More specifically, I would research roles:

• In my local area.

• Locations I would be willing to relocate to.

• Companies I would be interested in joining.

• Cleared roles if I held a clearance.

I would then build a simple spreadsheet tracking:

• Job title.

• Certifications required.

• Tools mentioned.

• Years of experience mentioned.

• Degree requirements.

• Salary ranges.

After reviewing around 30 to 50 listings, you will start to notice common themes and trends in roles.

At this point, you shouldn’t be asking yourself:

“What certification should I get?“

Rather:

“What do employers consistently require for the role I actually want to pursue?“

Reframing this question changes everything.

Too many people (myself included) waste time debating certifications and building long wish lists that don’t align with real hiring demand.

Step 3: Conduct a Brutally Honest Gap Analysis

At this stage, this is where I would compare and contrast my market research with my military experience.

Even if I didn’t have a cyber/tech-specific or adjacent role, I know now that my military service built some valuable transferable skills such as:

• Risk management mindset

• Incident response thinking

• Documentation discipline

• Process adherence

• Leadership under pressure

• Security awareness

• Integrity and Accountability

Cybersecurity is at its core all about managing risk and protecting people and systems. Veterans have already done this in practice, even if you don’t think you have.

But here is what I would do differently:

I would reframe my experience to appeal to cybersecurity recruiters and hiring managers.

Not:

“I managed 15 personnel.“

Rather:

“Led a 15-person team in a high-risk operational environment, ensuring procedural compliance and mission-critical system integrity.“

Then in a spreadsheet, I’d create three columns:

• Column 1: What experience the market requires.

• Column 2: Empty

• Column 3: What experience I currently have.

Column 2 will become your roadmap. In this empty column, you will highlight what you are missing to fill in the gap.

For example, if you’re lacking:

• Hands-on SIEM experience: Go ahead and build a homelab.

• Security+: Schedule it first and then start studying.

• Cloud exposure: Sign up for an Azure subscription and starting getting hands on learning cloud fundamentals.

• Framework knowledge: Study ISO or NIST standards.

This way, you take out any of the guesswork and create targeted improvement.

Step 4: Immerse Myself in the Domain I Chose

Cybersecurity is not something you master in isolation.

People have already walked the path. Learn from them instead of reinventing the wheel.

If I were pursuing:

Blue Team / Defensive Security

I’d follow:

• Day Cyberwox

• myDFIR

Offensive Security

I’d follow:

• Tyler Ramsbey

• TCM Security

• John Hammond

Governance, Risk & Compliance (GRC)

I’d follow:

• Dr. Gerald Auger (Simply Cyber)

• Steve McMichael (CPA to Cybersecurity)

• Boyd Clewis

Cyber Threat Intelligence

I’d follow:

• Gary Ruddell

This wouldn’t be just for motivation, but to understand how professionals think.

Hiring managers care about mindset as much as technical skill.

Step 5: Leverage My Military Advantages

If I had an active clearance, I would tenaciously target cleared roles first.

This is because having a clearance already can act a bridge into cyber, especially within defense contractor and government roles.

I would also use benefits intentionally:

• GI Bill

• SkillBridge

• Credentialing assistance

(For transitioning service members or veterans of other countries, please research and see what advantages you may be entitled to.)

Use your advantages to close specific gaps identified in your analysis, not to enroll in random programs that don’t align with hiring demand.

Step 6: Prepare for an Ego Adjustment (And Don’t Do It Alone)

The military is quick to give you responsibility from day one.

The civilian cybersecurity world may reset that (temporarily).

I had to start at the ground level all over again. To get my foot in the door, I accepted a junior role knowing that the long-term trajectory in cyber would make it worth it.

But here is something I would prioritise far more than I did:

I would not do this in isolation.

Transitioning out of the military can feel isolating enough. Trying to break into cybersecurity alone makes it harder than it needs to be.

If I were starting again, I would:

• Reach out on LinkedIn to professionals currently in the roles I am targeting.

• Ask them honest questions about:

  • What their day-to-day actually looks like.

  • Work-life balance

  • Stress levels

  • Meaningful vs. repetitive work

  • What they wish they had known

Most people are more willing to help you than you think, especially when you are respectful and specific with your questions.

I would also join professional communities such as:

• ISACA

• ISC2

• OWASP

Attend local chapter meetings.

Ask questions.

Be visible.

Beyond that, I’d join domain-specific Discord and Slack communities. Cybersecurity has extremely active online spaces where professionals openly share knowledge.

Cyber is a community-driven profession and the faster you jump in, the faster you will grow.

Final Thoughts

You do not need to reinvent yourself to break into cybersecurity.

You need to reposition yourself.

The discipline, resilience, and operational awareness you’ve built in the military are not weaknesses in this industry.

They are huge advantages.

You just have to apply them strategically, and surround yourself with the right people while you do it.