There’s a quiet problem I see over and over again with transitioning veterans (and it’s not a lack of skill, discipline, or experience).
It’s pride.
Not the healthy kind. Not the kind that comes from doing hard things and doing them well. I’m talking about the kind of pride that keeps you stuck. The kind that whispers, “I’ve got this. I don’t need anyone.” The kind that convinces you to struggle in silence while the world moves on without you.
Let me be clear. It’s killing your momentum. And if you don’t address it, it will kill your transition and post-military life as well.
In the military, especially in elite communities, self-reliance is baked into your DNA. You’re trained to figure it out. You’re expected to carry your weight. You’re surrounded by people who can execute under pressure without needing their hand held.
That environment creates an unspoken rule: Needing help equals weakness. That rule might serve you in a combat zone. It does not serve you post-military.
Out here, nobody is handing out awards for silent suffering. Nobody is impressed that you spent six months trying to figure out something that someone could have taught you in thirty minutes.
And yet, this is exactly what I see happening. Every day. Veterans spinning their wheels. Struggling to network. Failing to land interviews. Trying to build businesses with no customers. All while refusing to ask for help.
Let me say this as plainly as possible: You are not supposed to know everything. I tell people all the time: “The last Perfect Person walked the Earth 2000 years ago.” That’s not just a nice quote. That’s a reality check.
You are fallible. You are learning. You are transitioning into an entirely different operational environment. And yet somehow, many of you expect to show up on Day 1 in the civilian world and operate at 100% effectiveness.
That’s not confidence. That’s delusion.
Here’s the cost of refusing to ask for help:
Months (often years) of wasted time. Missed opportunities you didn’t even know existed. Bad decisions that could have been avoided. Burnout from trying to do everything alone. Frustration that turns into bitterness.
I’ve seen incredibly capable veterans stall out completely because they refused to raise their hand. Not because they weren’t good enough. But because they wouldn’t ask.
This isn’t theoretical. This is real. If you’re transitioning (or even years removed from the military) you probably need help in at least one of these areas:
Networking: You don’t know the civilian landscape. You don’t know who’s who. You don’t know how decisions actually get made in companies. So what do you do? You isolate. I did. You apply online. I did. You hope your resume speaks for itself. I did (and it won’t.)
You need people. You need introductions. You need conversations. And that means asking someone: “Hey, can you help me understand this space?”
Building a Resume That Makes Sense: Your military experience is valuable. But here’s the problem: Civilians don’t speak your language. They don’t understand your acronyms. They don’t know what your role actually means in terms of business impact. So you send out a resume that makes perfect sense to you… …and gets ignored by everyone else.
Instead of guessing, ask someone who’s done it before: “Can you help me translate this?”
Learning How to Sell Yourself: This one hits hard. In the military, your work speaks for you. Your rank, your position, your reputation, they each carry weight. In the civilian world? Nobody cares until you show them why they should.
You need to communicate your value clearly. You need to articulate outcomes. You need to sell. And if you’ve never done that before, pretending you have isn’t going to cut it. So ask: “Can you help me understand how to position myself?”
Starting or Scaling a Business: I see this all the time. A veteran decides to start a business. They’ve got discipline. They’ve got drive. They’ve got a logo, a website, maybe even an LLC. And then… Nothing. No customers. No revenue. Because they skipped one critical step: Learning from someone who’s already done it.
Instead of burning time and money, ask: “Can you help me understand how to get my first customer?”
Making Decisions in a New Environment: In uniform, decision-making is structured. There’s doctrine. There’s hierarchy. There’s clarity of mission. In the civilian world? Ambiguity is everywhere. You’re making decisions without the same framework. That’s uncomfortable.
So what do you do? You either freeze… Or you guess. Neither is a good strategy.
Find someone ahead of you and ask: “What would you do in this situation?”
Let me be honest about what’s really going on. It’s not just pride. It’s fear. Fear of looking inexperienced. Fear of being judged. Fear of being told “no”. Fear of exposing what you don’t know.
I understand that fear. But here’s the truth: People already know you don’t know everything. You’re not fooling anyone. The only difference is whether you’re willing to do something about it.
In the military, you understand force multiplication. You understand that the right support, at the right time, changes everything. Air support. Intel. Logistics. You would never walk into a mission and say: “Nah, we’re good. We don’t need any of that.”
And yet, that’s exactly how many of you are approaching your transition. You’re trying to run a complex, unfamiliar mission… …without support.
That’s not toughness. That’s poor planning.
Let’s remove the ambiguity. Asking for help doesn’t mean begging. It doesn’t mean being helpless. It means being intentional.
It looks like this: Reaching out to someone on LinkedIn and asking for 15 minutes of their time. Telling someone directly what you’re trying to accomplish. Being honest about where you’re struggling. Listening more than you talk. Applying what you learn.
That’s it. Simple. Definitely not easy, but simple.
If you’re going to ask for help, do it right. Don’t waste people’s time. Don’t be vague. Don’t be entitled. Be direct. Be respectful. Be prepared.
Here’s a simple structure that works: “[Name], I’m transitioning out of the military and trying to break into [industry/role]. I saw your background and would really value your perspective. Would you be open to a quick 15-minute call? I’m specifically trying to understand [insert specific challenge].”
That’s it. Clear. Focused. Respectful. And you’d be surprised how many people will say yes.
When you ask for help… You’re not just helping yourself. You’re giving someone else the opportunity to lead. To mentor. To give back. Most people who have achieved any level of success didn’t do it alone. They remember what it was like to be where you are. And many of them are more than willing to help. I know I am.
But they can’t help you if you never ask.
Another pattern I see? Veterans wait too long. They struggle quietly. They try to figure it out. They hit wall after wall. And only when they’re frustrated, burned out, and desperate do they finally reach out.
At that point, everything feels urgent. Everything feels heavy. And it’s harder to recover. Don’t wait for that moment. Ask early. Ask often. Stay ahead of the problem. Stay left of bang.
You’ve heard it before: “Your network is your net worth.” It’s not just a cliché. It’s reality. Opportunities don’t just appear. They come through people. Introductions. Conversations. Referrals. And none of that happens in isolation.
If you’re not actively building relationships (and asking for help along the way), you’re limiting your own access to opportunity.
You didn’t operate alone in the military. You had a team. You relied on each other. You trusted each other. Why would you expect your post-military life to be any different? It’s still a team sport. The only difference is that you have to build your team.
And that starts by reaching out.
So get over yourself. I don’t say that to be harsh. I say it because it’s necessary. Your pride is not serving you. Your silence is not helping you. Your reluctance to ask for help is slowing you down.
You’re capable. You’re valuable. But you are not perfect. None of us are. I know I’m not.
So stop pretending you have it all figured out. Raise your hand. Start the conversation. Ask the question.
Because the veterans who succeed in transition aren’t the ones who try to do it alone. They’re the ones who understand something simple: Winning after the military still requires a team.
And teams are built one conversation at a time.
