Introduction

It was a privilege to join Omar Sangurima and Alyson Laderman recently on The Cyber Mettle Podcast to talk about a topic that is deeply personal to me: the transition from high-stakes operational roles, like military service, into the civilian cybersecurity sector. I am very passionate about my field, and this topic is near and dear to my heart.

While my start in cyber was perhaps unconventional, the experience I gained in the defense space for over a decade (between military service and defense contracting) has been the single most critical factor in my civilian career. I'm currently a guardsman and fully entrenched in the civilian world, giving me a unique perspective on managing both. I've kind of done most of the cyber things, from network administration to pen testing.

These lessons aren't just for veterans. They are for anyone looking to advance their career by communicating their unique value in a crowded field.

Here are some high points from our conversation - most of which I had to learn the hard way:

The Translation Problem: Stop Talking Jargon, Start Quantifying Value

If you are transitioning into a new role, whether from another industry or simply moving up the ladder, you likely struggle to explain your past work using the right language. The biggest issue I see (and have experienced) is the inability to translate technical or specialized jargon into tangible corporate value.

When I mentor people, I tell them: Your experience is a solution, not a story.

Be Quantifiable: Instead of listing responsibilities, list results. You need to find a way to quantify the value you bring.
Use Business Language: Focus on terms that show value, like risk management, strategic planning, and logistic optimization. For example, the military taught me the "do more with less" mentality, which directly translates to efficiency and solving problems in resource-constrained environments.

The goal is to master the message you send to people and be direct about the specific value you bring.

The Soft Skills X-Factor: Leadership in High-Stress Environments

In many roles, we're taught to be "silent professionals" focused only on the machine. We are often more comfortable being part of a team than individually taking credit. I still struggle with this myself, especially during performance reviews.

However, the rapid responsibility given in fields like the military hardens a set of soft skills that become your X-Factor in the civilian world.

Case Study: My Interview Tie-Breaker

When I was interviewing for my current role, the final 30-minute call was unstructured. I realized everyone had the same technical prep. I decided to pivot and got personal and direct.

I emphasized my ability to:

Lead very technical teams with very strong type-A personalities.
Lead teams in extremely high-stress environments.
Be pointed in a direction and simply figure something out.

My past experience gave me the confidence to say, "If that’s someone you want, I’m your man." That directness, backed by mission-driven experience, might have been the key differentiator that landed me the job.

The Communications Gap: Navigating Corporate Tone

The "no BS culture" common in high-stakes operational roles, where we feed information very directly, often clashes with the civilian world, where tone is heavily policed. I had a manager once tell me my emails were too direct with clients, as I was the kind of guy who would just respond with “done.”

Here’s what you can do about it:

Find a Sanity Check: Find a trusted co-worker or advisor who can be your sanity check, someone who will shoot you a side message in a meeting and tell you to "tone it back a little".
Leverage AI: I often use tools like Gemini to help me phrase conflicts or feedback professionally, especially when I don't naturally have anything "nice" to say. Use the tools you have to avoid unnecessary conflict.
Embrace the Directness (Carefully): You may be the person your team needs to cut through fluff and challenge people. My ability to show up and say things "suck" and then write it up in a neatly written form is a core strength of consulting. But having corporate buy-in before you become the direct person is crucial.

Your Next Mission: Finding Purpose Beyond the Paycheck

One of the deepest struggles in transitioning is the potential loss of a mission-oriented identity. You might be paying the bills, but you miss knowing that you have impact.

I encourage people to approach their current job search or career phase as their "next mission" (with the same planning and perseverance you would a mission).

But what about fulfillment? (Here’s what works for me at least)

Volunteer Strategically: To find purpose, I look for outside opportunities like volunteering with organizations whose mission I am passionate about or can align with.
Network with Intent: I’m terrible at networking, as I’m more of an ambivert and prefer not to be in large groups. I let my work speak for itself. When I do network, a friend (thanks, Santosh) taught me to look someone in the eyes and ask them what they love about what they do, about their hobbies, or about their passion projects. People are more than what they do and they might be tired of the rat race too. This helps find a genuine connection rather than approaching it as a transactional interaction.

What Now, Airman?

Your next step is to reframe your value and move with confidence. You have the skills and the expertise; just keep going, be the hardest worker in the room, and fight the good fight.

You can hear more about my journey, including the candid conversations with Omar and Alyson, by listening to the full episode of The Cyber Mettle Podcast! We dive into topics like: