Catching Up: How VA Benefits Help Military Officers Transition to Civilian Life

I had the opportunity to catch up with my friend of 30 years, Ken Hockycko , who recently retired from the Navy and is starting his own entrepreneurial journey. Our conversation was a reflection on our shared experiences, the challenges of transitioning from military service, and the opportunities that lie ahead.?

Retirement from the military is a strange thing. After 20-plus years in uniform, you transition from an environment where your identity is tied to your rank, your billet, and the insignia on your chest to a world that doesn’t care much about any of that. You quickly realize that no matter how impressive your military resume may be, civilian employers aren’t necessarily lining up to offer you a corner office. And honestly, why should they?

Ken and I were classmates at the United States Naval Academy ?and Plebe Summer Detailers together but spent our careers in vastly different parts of the Navy. Ken flew F-14s and Super Hornets, graduated from Top Gun, and served in some of the most elite aviation commands in the military. I took a different path—first to submarines, then to law school and the JAG Corps. But despite our different careers, our experiences leaving the military have been remarkably similar.

The reality is that leaving military service—especially for those of us who retire—is a reset. It’s not the same as a civilian job transition, where you climb a ladder and move up. It’s more like stepping off a moving train and realizing you have to start running again, just to keep up. Our civilian peers spent their 20s and 30s building careers, climbing the corporate ladder, and compounding their earnings. Meanwhile, we were deploying, leading teams in high-stakes environments, and operating under a fixed military pay scale. That’s where VA benefits come in.

A lot of veterans hesitate to take advantage of the benefits they’ve earned. Some see it as a handout, others feel that because they’re not "broken" in an obvious way, they don’t deserve these benefits. But there is another perspective. VA benefits—whether it’s the GI Bill, disability compensation, or a military pension—aren’t charity. They’re part of the covenant we made with the country when we signed up to serve, and they are intended to empower veterans to continue their impact after taking off the uniform.

Ken and I have both leaned into the resources available to us. For me, the GI Bill was a game-changer. It allowed me to go to business school and pivot into a completely new career. It gave me the flexibility to take risks, explore new paths, and ultimately start my own business. The pension and disability benefits provided a financial cushion that let me focus on learning instead of scrambling for the first paycheck I could find. Ken is now navigating this process himself, and we’ve had long conversations about how to best use these benefits to set up the next phase of his career.

One of the biggest challenges for transitioning veterans is realizing that, while our skills are valuable, they don’t always translate directly. Leadership, decision-making under pressure, and mission focus are all great qualities—but they don’t automatically make you a CEO, an investment banker, or a startup founder. That takes learning, adaptation, and often, a willingness to start lower on the totem pole than you might expect. Tim Cook, the CEO of Apple, isn’t going to take over a combatant command tomorrow just because he’s a great leader. The reverse is true for military officers entering the private sector.

But here’s the good news: we aren’t starting from scratch. The benefits we’ve earned give us the opportunity to make smart choices and set ourselves up for success. They allow us to take calculated risks, whether that means going back to school, taking an internship, or starting a business. They give us the freedom to learn, to grow, and to find a new mission.

One of the things Ken and I talked about at length was how veterans should not only embrace these resources but also shift their mindset about what comes next. The challenge is not just about finding a new job; it’s about finding a new purpose. For years, the military defined who we were—our mission, our roles, our responsibilities. Now, we have to define it for ourselves.

Ken and I have had some great conversations about this over the past year, and I’m excited to see where his next chapter takes him. For anyone else standing at that transition point, my advice is simple: take full advantage of what you’ve earned, lean on your network, and remember that the best is yet to come. The world isn’t closing in—it’s opening up.

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