My Veteran Story (Part 2)
This post continues my story from Part 1.
In this part, I dive into the more specific things that I engaged with during my struggles. From resume writing, to interviewing, to finding the new identity that needed to forge. If you’re in the middle of your transition, I think this is one that will provide the best value to you, especially as you become more comfortable with assessing whether the advice someone else provides you is worth your time.
“It felt like a coach yelling, “Just score more points!” while refusing to explain the rules of the game.”
6. What advice did you hear the most during your transition—and what advice did you actually need?
This is where I will start to talk about resumes… a lot. If it feels like I talk about them too much, that’s because I think we put way too much focus on them overall, but learning how to write one is the first truly tactile thing that comes out of the transition, so of course we focus on it.
Everyone wants to see it. Everyone wants to fix it. Everyone has opinions. So, I’m going to bring it up more than once, because it’s the challenge we all grapple with, whether we like it or not.
I grappled with it almost nonstop.
I read every transition guide I could get my hands on. The books, the blogs, the boot camps. To be clear, most of it was written with the best intentions. A lot of it was technically good advice. Stuff like: tailor your résumé to every job, highlight your impact, network every day, write better cover letters, make coffee dates your new MOS. I did all of that.
No joke, I had 75 versions of my résumé on my hard drive. I customized them for every job. Spent hours on each cover letter. I commented on LinkedIn posts, reached out to mentors, did informational interviews. I followed the playbook.
And you know what?
Nothing really moved.
That’s when I realized something was missing. Everyone was telling me what to do, but no one could explain how to do it in a way that made sense for someone like me. The advice was abstract. General. Vague. Everyone said “show your impact,” but when I tried, I’d get the same feedback over and over: “Okay, but what did you really do?”
I remember sending a résumé to a friend. I had a bullet on there that said something like, “Managed $270 million worth of property with zero loss over 20 months, the first to do so.” And his response? “You need to show what you actually accomplished.”
And I’m sitting there, losing my mind, thinking… what? Isn’t that the accomplishment?
It felt like a coach yelling, “Just score more points!” while refusing to explain the rules of the game.
Then I realized that I wasn’t missing effort. I was missing context. The bullet wasn’t wrong, but it wasn’t enough. What I needed to say was that I built a delegated management system that enforced accountability and documentation across seven or eight departments and five or six levels of authority, resulting in zero losses, all while still preserving time for training and without increasing admin burden. That’s what hiring managers want: the “how,” not just the “what.”
That’s not a thing we get taught well because:
Most veterans only go through the transition once.
They don’t necessarily understand what made them hirable. They just know they got hired. Now they’re giving advice from the other side of the wall, not realizing how little they’ve reverse-engineered the process. By the time we get smart enough about hiring decisions, we forget how lost we all felt during this process and don’t have time to close the loop.
That’s the blind leading the blind.
Even the people who mean well, and I truly believe most do, often give you their path, not a path. And when it doesn’t work for you, the implication is that you must be doing something wrong.
What I needed was someone to say: “You’re not missing something, this just isn’t working right now, and that’s okay.”
I didn’t need another checklist. I needed permission to feel lost. I needed someone to say, “Hey, it’s okay to be uncertain. To not have a dream job lined up. To feel like a stranger in your own skin. To question your worth now that you’re not wearing the uniform.”
Instead, all the advice I got assumed I already had clarity. That I knew who I wanted to be. That I had some stable vision of success.
I didn’t. I think a lot of people don’t.
The emotional side of transition is completely under-discussed. All the guides talk about résumés and networking. None of them talk about identity, grief, or the sense that your internal compass just got smashed.
That’s what I needed. Not another template, but someone willing to admit they were scared too.
So I built that space myself.
“Most veterans only go through the transition once.
They don’t necessarily understand what made them hirable. They just know they got hired.”
7. Did you run into any grifters, fake opportunities, or LinkedIn nonsense?
Oh yeah. But not always in the way you'd expect.
It wasn't some guy in a hoodie trying to sell me fake crypto. It was more subtle than that, more insidious for me. The worst offenders weren’t scammers. They were philosophy grifters. Thought leaders. Hustle prophets. People selling you their version of success as if it were gospel. They preach grind culture like it’s a sacred rite. And if you don’t buy in? You’re soft. You don’t want it bad enough.
I remember one guy in particular, a senior manager at Amazon. We were talking about transition, and he launched into this proud little war story about canceling his dentist appointment because his boss called him needing a report done. So he sat in the waiting room, laptop open, hammering out numbers while his cavities grew. He told me that this was the only way to succeed outside the military. I hadn’t had a job on the outside yet, but I was pretty confident that was wrong.
He wore it like a badge of honor. Like this was what it meant to be dedicated. Like this was the kind of sacrifice that proves your worth.
I remember sitting there thinking: “Absolutely none of this is valuable to me.” I didn’t want that life. I didn’t want to become that story. More importantly, I didn’t respect it.
That moment crystallized something for me: not all advice is worth taking. Just because someone found success doesn’t mean they found your kind of success.
I had spent months at that point drowning in advice. Resume tweaks. LinkedIn tactics. Cold email scripts. And now here was a guy telling me the real secret was to cancel your damn dental appointments.
That led me to the realization that just because someone’s farther down the road doesn’t mean they know where they’re going. Or that you should follow them.
So yeah, I ran into nonsense. But it wasn’t always a scam in the traditional sense. It was a mismatch in values disguised as mentorship. And that can be just as dangerous.
My lesson? You don’t owe reverence to every veteran who made it out. You don’t have to inherit someone else’s definition of success. You’re allowed to evaluate the advice you get. You’re allowed to say, “Thanks, but that’s not for me.”
That one realization was more liberating than any resume rewrite.
8. What’s something that didn’t make sense until months—or years—after you got out?
Conviction.
When you leave the military, you’re not just walking away from a job. You’re stepping out of a belief system. What nobody tells you is how long it takes to build a new one.
At first, everything feels up for grabs. Every suggestion feels like a command. Every job offer feels like salvation or a trap. You listen to every podcast, every mentor, every blog post, and every dude who “found success” and wants to reverse-engineer it for you.
But until you figure out who you are, and what you actually want, it’s just noise. Conviction is the filter.
It took me years to find mine.
I spent so much time chasing opportunities that made sense on paper but didn’t resonate. I didn’t know how to say no, because I hadn’t defined what “yes” looked like. Every path seemed plausible. I got wrapped up into seeing every opportunity through the lens of what I could do instead of what I wanted to do. That was the conviction that I needed.
That clarity doesn’t come from figuring out your résumé. It comes from doing the hard emotional work of rebuilding identity, without a uniform to hide behind.
Once you have conviction? Suddenly the roads don’t all look the same. Some lead toward you. Some lead away. Some are rough. Some are paved. Hell, some are just deer trails.
You finally know which ones to walk because you’re able to figure out which roads you like.
9. Was there a moment you thought, “This is the first time I’ve felt like myself again”?
There’s this ebb and flow that’s defined my entire transition. I don’t see it as a single event, I see it as a long, messy process. And throughout that process, there have been moments, not of returning to who I was, but of realizing that I’m actually okay being who I am now.
One of the first of those moments came during what should have been the most boring thing in the world: building a spreadsheet.
I was tasked with creating our company’s annual operating plan. We didn’t have an ERP system or even a real finance tool at the time, so I built it all in Google Sheets. I gave every department head their own sheet to input forecasts, and then built a real-time calculator that pulled it all together. Live updates. Rolling forecasts. Version control. It was ugly, but it worked.
For the first time since taking off the uniform, I felt proud in the same way I used to feel proud when a training exercise came together or a range day went well.
Not because I had briefed a general officer. Not because I had coordinated a combat mission. I had taken a massive, unwieldy problem and built something real, something that other people relied on.
That was one of the first moments where I looked at myself and thought, “I can belong here.”
Another one? This website. Veteran Casual. The stories. The writing. The process of sitting with another veteran and helping them unravel their experience into something coherent, raw, and honest.
I’m a storyteller. I always have been. And there’s something about interviewing someone, really sitting with their experience, hearing them find the words for what they lived through. That makes me feel like I’m doing what I’m supposed to be doing.
Let’s be honest, outside of therapy, when do you ever get to sit down and talk about your life, your fears, your questions for hours? We don’t. We don’t make space for that. Here? I do. And it’s meaningful (for me, at least).
Those moments don’t look like what I thought they would. They look like complex spreadsheets and long-form interviews. They look like clarity. Like usefulness. Like presence.
Not a return to the old me. But an arrival at the new one.
10. When did you first realize life outside the military wasn’t going to kill you?
It really clicked when I changed jobs for the first time.
I had been working at my first post-military company for about 18 to 20 months when I got recruited to be a Chief of Staff at a startup. Unlike every other opportunity I’d had, I didn’t know a single person at the company and had no real shared history. No fellow veteran sliding my resume to the top. Just me, raw, in the open market.
That was the first time in my adult life I felt like I truly earned something without the scaffolding of a military network or personal connection placing me in the role. I had built trust through my interview alone. I had walked into a new world, pitched myself to some of the smartest people I had ever met, and made the cut.
Don’t get me wrong, I had earned a lot of things before: my spot as an aide-de-camp, my time as a company commander in a senior Special Forces billet, even my first job out of the military. But this felt different.
I was also scared. These were some of the sharpest, most capable people I’d ever worked with. It was tech. It was fast. It was intense. It demanded skills I didn’t yet have. I showed up anyway.
That’s when I realized: life outside the military wasn’t going to kill me. In fact, it might actually reward me if I kept betting on myself.
I didn’t feel like I had "made it." I felt like I belonged. That was enough to steady the base plate. That was the shift from being a transitioning service member to being a veteran.
Thinking about it now, I have a blog post up where I talk about how the transition process isn’t a mission to complete, it’s a new mythos to write. This was part of my own transition where I got to choose that this moment mattered, that this was part of my definition of success.
“I’ve had to learn how to be honest with myself about what I actually want. That’s the biggest change.”
11. How has your definition of success changed since leaving the military?
I’ve had to learn how to be honest with myself about what I actually want. That’s the biggest change.
When I got out, I still carried the soldier’s mindset that the team is everything. Success was about unit performance, not personal ambition. But over time, I started to wrestle with something deeper—something I didn’t always feel comfortable admitting:
I care about money.
I care about title.
I care about having influence, about being able to shape outcomes, and about doing work that actually matters to me.
In the military, that kind of personal ambition feels taboo. Everything is team-first. Your compensation is public. You don’t get bonuses. You don’t get to define success on your terms. It’s defined for you, by rank, rating, or role.
After almost five years out, I’ve learned that wanting things for myself isn’t selfish, it’s grounding. I want enough money to live well. I want a role where I’m respected for my mind, not just my work ethic. I want to do things that align with who I am, not just what the organization needs.
All of that requires conviction. Which only comes once you’ve started to rebuild your identity beyond the uniform.
As that identity has solidified, I’ve been able to better define my values. It’s not that I don’t care about teams, I still care deeply about my team. But I’m part of the team. I matter too.
Success, now, is about alignment: between what I value and what I do. Between how I see myself and how I show up. Between what I want and what I’m building.
That’s a definition I couldn’t have articulated in my first two or three years out.
Now it feels like the only one that actually fits.
“What you’re feeling isn’t weakness. It’s grief.”
12. What would you say to yourself on the day you signed out for the last time?
You're not alone in being afraid.
The confusion that you feel, the fear, the frustration, the uncertainty about what you will do now, all of that is normal. Every single person who has ever transitioned out of the military, no matter how dialed in their plan was, experienced fear. It might have lasted a day or a year. It might have been buried under bravado, but it was there.
What you're feeling isn’t weakness. It’s grief.
This isn’t just a new job. This is an identity fracture. You're stepping away from something that shaped you. From a culture, a mission, a sense of belonging. From a version of yourself that you knew how to be.
It’s okay to mourn that.
It’s okay to look at LinkedIn and feel behind. To see others with shiny job titles and wonder if you're failing because your path isn’t so clear. It’s okay to feel like you’ve lost your footing. Like you don’t know who you are without the uniform. You’re going to see someone that you once outranked shoot ahead of you in their post military career. You’re going to see a peer fall wildly behind.
You haven’t figured it out yet. That’s not a flaw, that’s just the beginning of the transition process.
You don’t have to fix everything today. You don’t have to have the next five years mapped out. You don’t need to know your purpose yet. What you need is to survive this moment, to accept that this uncertainty is the price of transformation.
You will transform.
This isn’t the end. It’s a transition. And you will emerge from it, maybe not quickly, maybe not cleanly, but you will. It’s not a clean sequence. Sometimes you’ll look around and see yourself ahead, then you’ll look around and see yourself behind. Remember that it’s a process, not an event.
Let yourself be afraid. Let yourself grieve. Let yourself sit with the discomfort.
Because the only way out is through.
13. What’s something you miss that surprises you?
I miss the field.
Not the conditions, not the bugs, or the cold, or the terrible food. I miss the absurd humanity of it. The parts that strip people down to their raw, unfiltered selves.
Out there, you found out who the “dirty birds” were, who didn’t brush their teeth, who thought changing socks was optional, who forgot deodorant is a public service. You found out who had a sense of humor, and who took themselves way too seriously. You found out who kept the morale up when the mission slid off the rails, and who disappeared into the background when it did.
I miss the boredom too. That specific kind of “hurry up and wait” boredom that led to endless games of Spades, dumb competitions, and shit-talking that could go on for hours without losing steam. I hated it in the moment, like everyone else did. But it was real. You couldn’t fake it out there. And that kind of shared discomfort has a way of forging bonds that stick.
Sure, you can go hiking. You can go camping. But it’s not the same.
You can’t recreate the feeling of being in the dirt with people who have your back and know exactly how you take your coffee.
What surprises me isn’t that I miss the people. Of course I do.
What surprises me is that I sometimes miss the chaos that revealed who those people really were.
