The Power of Connections

At VetSecCon '24, I discussed how service members transitioning to the civilian sector can navigate the challenges by building a resilient support network. If you missed out (or your preferred learning method is reading), here's a snapshot of that talk.

In 2015, while forward deployed in Kuwait as a Marine Staff Sergeant, I found myself in a conversation that would alter my trajectory. My Marine, Corporal Ryan Osullivan—one of the best I’d worked with—was preparing to leave the Corps. Doing my due diligence as a Staff Noncommissioned Officer, I asked Cpl Osullivan about his plans for the upcoming transition. Unlike many other young Marines I had spoken to about their transition, he had a clear plan: a school picked out, a defined path forward, and actionable steps already in motion. As I listened to him, I had a realization so jarring it sent a wave of panic through me: I had been in the Marine Corps for 12 years and not once thought about my transition. I had spent years advising young Marines on planning their futures, yet I had never applied that wisdom to myself. It was at that moment that my transition story began.

The military provides a structured existence. Everything is laid out—from promotions to duty stations, professional development, and career progression. There is an expected rhythm to life in the service that can lull a person into a false sense of security. In my case, I had already laid out a general path leading to retirement. I knew the courses I should attend, when to expect a review for promotion, and which duty assignments would help my career progression. Whenever unsure, I could talk to my senior leaders or read the readily available regulations.

But in the civilian sector, everything shifts. The neatly arranged steps dissolve, replaced by a nebulous and often overwhelming landscape where two people with the same job title might have vastly different roles and responsibilities. The path is no longer linear; it becomes an uncharted “choose your own adventure.” There is no right or wrong way to enter your desired field or progress in your career.

For service members leaving the military, uncertainty is their greatest enemy. Many resources exist to help service members transition: transition assistance programs, workshops, and mentorship networks. But it can feel like a firehose of information. The sheer volume makes it difficult to discern what is relevant and what is noise. Some programs are under-advertised, and others have stringent requirements that limit when you can apply. Alarmingly, some programs are predatory, preying on vulnerable veterans seeking direction. Time is a limited resource, and spending too much on a program that isn't the right fit can have an outsized impact on the transition.

In the face of this uncertainty, I have found that the most effective navigational tool is not a website, a seminar, or a checklist—it’s people. Connecting with people and building relationships will go a long way toward creating a support network that will enable success beyond the transition. The first step is to find mentors. Having a mentor is critical because they provide lived experience and insight that no amount of Googling can replicate. Every conversation I’ve had with a mentor has provided new knowledge, exposing blind spots, revealing skills I hadn’t considered valuable, and pushing me toward growth.

Mentorship, however, is only half of the equation. Building connections is a two-way street; it requires giving as much as taking. A successful transition requires a shift in mindset—prioritizing relationships not for transactional gain but for mutual support. This is what is called an “outward mindset.” Instead of being the main character in your own story, it’s about recognizing the needs, objectives, and challenges of others. Then ask yourself: How can I help this person fulfill their needs? Overcome their challenges? Meet their objectives? By focusing on how to help others, we inadvertently build networks of advocates—people who, recognizing our generosity, seek to reciprocate. Opportunities emerge organically when we invest in others without expecting immediate returns. (For more, read The Outward Mindset by the Arbinger Institute)

For those unsure where to begin, start where commonality exists: veteran organizations. Groups like VetSec, the Veterans Beer Club, Operation Code, and VETCON provide spaces where the shared experience of military service bridges initial awkwardness. Many veteran groups have established formal mentorship programs that can bring awareness to issues unique to transitioning service members. But this is only the beginning; most of the population has never served in the armed forces, so extending the search beyond veterans is crucial. Many groups are available to help those interested in cybersecurity, such as DEFCON, Null 404, WiCyS, or CSA. LinkedIn, particularly with its free premium membership for service members, can be a powerful tool for connecting with professionals in target industries. You'd be surprised at how many people are willing to talk about their career path (Steve Dalton provides a proven method for conducting informational interviews in his book The 2-Hour Job Search). A simple outreach—asking someone in a role you admire for a conversation—can yield surprising results.

And then, there’s volunteering. If you want to integrate into a community and seen as someone who contributes rather than seeks assistance, volunteer. In cybersecurity, organizations like Security B-Sides run entirely on volunteers and provide a prime opportunity to work alongside industry professionals. Beyond career-focused efforts, any act of service—mentoring, coaching, supporting local initiatives—signals to others that you are invested in something greater than yourself.

My journey illustrates the power of this approach. That night in Kuwait in 2015, after my conversation with Cpl Osullivan, I enrolled in a college course with no clear direction beyond an interest in IT. Over the years, through mentorship, volunteering, and intentional networking, I refined my focus to cybersecurity. Every conversation with a mentor led to tangible refinements to my transition plan. I learned new details about my chosen career, where to focus my effort, and the challenges I will face. A mentor introduced me to the Leader Transition Institute and their Changing Focus program. They were so helpful to me that I volunteered to serve alongside them as a director, helping others navigate their transitions. I'm confident that the help I've received over the years has set me up for success well beyond the end of my military career.

The greatest lesson I’ve learned is that the military transition is not just about finding a job but building a life. It’s about forging relationships, creating opportunities for others, and allowing those connections to create opportunities in return. The structured world of the military may provide a sense of security. However, with all its unpredictability, the civilian sector offers something even better: the chance to shape a future beyond what we imagined possible.

So, to those standing at the threshold, feeling the same existential dread that gripped me years ago, know that you are not alone. Seek mentors, give freely of your time, embrace uncertainty, and trust in the power of human connection. The way forward is not laid out in a field manual but is there, waiting to be discovered—one connection at a time.