Every single week, I talk to retiring and transitioning veterans. Doesn’t matter if they’re E-8s, O-6s, Green Berets, or logisticians who have kept brigades moving for decades. And every single call, early on, I ask the same two simple questions:
Where do you want to be (geographically)?
What do you want to do (professionally and personally)?
That’s it. Two straightforward questions. Not trick questions. Not philosophy exam questions. Just practical ones.
Why do I ask? Because if you can’t answer these, you’re not ready to transition. At a minimum, these should be locked into your head before you hang up the uniform.
Here’s the scary truth: most people can’t answer either one.
Even the elites. Even the folks who spent careers solving complex, dangerous problems under pressure. They’ve fought terrorists, run multi-million-dollar budgets, and led teams into battle… but when it comes to their own lives, they stumble. They give me vague nonsense like:
“Somewhere warm.” “Something with leadership.” “I’m open to anything.”
That’s not clarity. That’s confusion dressed up as flexibility. And confusion gets you eaten alive on the outside.
You’ve been trained your entire military career to put the mission first. To think about others before yourself. To focus on the objective and your team. That’s honorable, but here’s the problem: your transition is not a mission for someone else.
It’s the first time in your career where you are the mission. And if you can’t define the target, how in the hell are you going to hit it?
Think about it like this:
Geography tells me your environment. You can’t fish part-time in Chicago, and you won’t get Silicon Valley executive gigs in rural Alabama. Place matters. Where you live drives the opportunities, the cost of living, the community, and yes, even your happiness.
What you want to do tells me your purpose. Are you chasing wealth? Flexibility? Impact? Are you chasing a dream you’ve always shelved, or do you just need stability after years of chaos? If you can’t articulate this, you’ll fall into the first “veteran-friendly” job that waves a flag in your direction (and three months later, you’ll hate both it and your new life).
If you can’t answer these two questions, everything else is just noise: your resume, your LinkedIn profile, your interview skills. Without direction, you’re spinning your wheels.
When I ask veterans where they want to be, I usually get a blank stare. Then the excuses roll in: “Well, it depends on the job.” “Wherever I can get hired.” “I’m not picky.”
Wrong answer.
Geography isn’t just a backdrop; it’s a strategic choice. The military taught you that terrain dictates tactics. Same thing in civilian life: location dictates opportunity.
Want to break into tech? You’re not doing it in the middle of nowhere. You’d better be in Austin, San Francisco, Boston, or one of the emerging hubs.
Want a quiet life with low cost of living and fishing every weekend? Don’t tell me you’re job hunting in Manhattan.
Want to stay close to family? Great, but recognize what industries exist in that region (and what doesn’t).
Here’s the hard truth: some of you are going to have to make tough calls. If you want big money and big titles, you’ll need to go where the action is. If you want peace, land, and simplicity, you may have to sacrifice prestige and paycheck. You rarely get it all.
But you do get to choose. And making that choice upfront saves you from wasting years chasing opportunities in the wrong place.
When I ask people what they want to do, this is where most people choke. When I ask, “What do you want to do?” I don’t mean “what job titles are you chasing?” I mean: what kind of life are you building?
Do you want to: Climb the corporate ladder and be a high-powered executive? Start your own business? Teach, coach, or give back? Work part-time and fish the rest of the week? Be hands-on (construction, trades, craft) or strategic (boardrooms, consulting, startups)?
If you don’t know the answer, you’re basically saying, “I’ll let life decide for me.”
But guess what? Life doesn’t care about you. Companies don’t care about you. Recruiters don’t care about you. They’ll shove you into the first box they think you fit. And once you’re in that box, it’s damn hard to crawl back out.
Here’s the blunt truth: if you can’t define what you want, someone else will define it for you.
So why do so many veterans fail at answering these simple questions? I see three main reasons:
The Military Never Forced You to Choose: For 20+ years, Uncle Sam told you where to live and what to do. Orders came down, you executed. You never had to pick your own mission. Now you do (and it’s terrifying).
Fear of Being Wrong: “What if I pick the wrong path?” Here’s the newsflash: you probably will. But the wrong path is still progress. Standing still because you’re afraid to choose? That’s failure.
Confusing Flexibility With Clarity: Veterans love saying “I can do anything.” Sure, you can. But employers don’t want “anything.” They want someone who knows exactly who they are and what value they bring. Generalists drown in a sea of specialists.
Let me tell you what happens when you transition without clarity:
You end up in a job that looks good on paper but feels like a prison.
You chase money but burn out because you never cared about the work.
You bounce from role to role, city to city, thinking the next one will magically fix your dissatisfaction.
You blame civilian employers for “not getting veterans” when in reality, you never got clear on what you wanted.
I’ve watched it happen over and over. I’ve seen absolute warriors (people who could command in combat), reduced to mid-level managers in jobs they hate because they didn’t spend the time figuring out their own two answers.
At a bare minimum, when you start your transition, you need to have the following locked in:
Geography (Top 3 Choices)
“I want to live near family in North Carolina.”
“I want to be in a major business hub like Dallas or Atlanta.”
“I want to stay in the Pacific Northwest for lifestyle reasons.”
Don’t tell me “anywhere.” That’s laziness, not flexibility.
Purpose/Profession (Clear Statement)
“I want to lead operations teams in logistics.”
“I want to start my own security consulting business.”
“I want a flexible role that lets me teach, coach, and mentor.”
Deal Breakers
“I don’t want to travel more than 20%.”
“I don’t want to work for defense contractors.”
“I don’t want to live in the Northeast.”
This clarity gives you a filter. It tells me, and anyone in your network, exactly how to help you. Without it, you’re just another veteran sending out resumes into the void.
If you’re reading this and thinking, “I don’t know what I want,” don’t panic. Here’s a process:
Audit Your Past: What parts of your military career energized you? Training? Operations? Strategy? Problem-solving? People? Those clues matter.
Define Your Non-Negotiables: Family, freedom, money, stability, creativity… rank them. What matters most to you in the next chapter?
Test Small: You don’t have to commit forever. Do informational interviews. Shadow someone. Take a course. Start a side hustle. You’ll know quickly if it feels right or wrong.
Set a Timeline: Indecision is death. Give yourself 30 days to come up with your top 3 geographic choices and top 3 professional options. Then move forward.
But I hear ALL the excuses:
“I’ll go where the job takes me.”
“I’m open to anything.”
“I don’t want to limit myself.”
Bullshit. Those are just ways to avoid making a decision. And if you don’t make the decision, someone else will; and you probably won’t like it.
Transition isn’t about keeping all doors open. It’s about slamming shut the ones that don’t fit you so you can walk confidently through the right one.
Here’s the blunt truth: The military may have shaped you, but the civilian world won’t save you. Nobody cares if you were a Green Beret, a pilot, or a supply sergeant… if you can’t answer two simple questions: Where do you want to be? What do you want to do?
If you can answer these with confidence, you’re already ahead of 90% of your peers. If you can’t, you’re just drifting. And drifting is no way to start the next chapter of your life.
So stop hiding. Stop waiting for the perfect opportunity to magically appear. Get clear. Get specific. And then (just like you did your entire career), execute.
Your next mission isn’t overseas. It’s your life. And you’re the commander now.
